☀ Perched on the Back Shore ~ 1 mile or 5min drive to Good Harbor Beach ☀ 22 acres to explore including: formal gardens, cranberry bog, pond, fountain and spacious lawns ☀ Ocean views on 2nd and 3rd floors ☀ Yoga studio on 2nd floor and gym w/Peloton on 1st floor ☀ Updated kitchen with butler's kitchen for entertaining ☀ Game room with pool table ☀ Large primary suite ☀ Library stocked with books + games ☀ Hi-Speed WiFi and Smart TVs The space Welcome to Cranberry Hill, your private estate perched on a hill overlooking East Gloucester's stunning Back Shore. The sprawling 22 acres was designed by Ezra Phillips in 1924 and carefully preserved while updating with modern conveniences. Enjoy grand formal rooms, cozy sunrooms, a spacious entertainment kitchen, and a luxurious primary suite. Conveniently just minutes to Rocky Neck, Bass Rocks Golf Club, and Good Harbor Beach. With almost 9000 sq feet across 3 floors this space is perfect for groups of all sizes to gather or spread out as they wish. 5 Min Drive to Good Harbor 5-10 Min Drive to Gloucester's Main Street (Beauport Hotel, Cruiseport, etc) 30 Min Drive to Salem Experience Cranberry Hill With Us & Learn More Below! ☆☆ FIRST IMPRESSION ☆☆ Pass through Bass Rocks Golf club and enter the coveted Way Road enclave as you make your way up Cranberry Hill. The long gravel drive provides plenty of parking for multiple cars in front of this private estate. Head into the grand front entrance or choose the side entrance where you'll find a convenient mudroom to return from beach trips. ☆☆ KITCHEN, DINING, SUNROOM ☆☆ Entering through the side entrance you're immediately greeted by a bright and warm floral wallpaper. To your left you'll find a convenient mudroom/laundry room with plenty of space to kick off shoes and throw beach clothes in the washer and dryer. Enter the light filled eat-in kitchen with comfortable window seat overlooking rolling green lawns. The classic and updated kitchen is well-equipped with stainless steel appliances, a center island, and no shortage of counter space. Two sinks, two dishwashers and a double oven make this the ideal spot for a large group to cook. And if this wasn't enough space, walk over to the large butler's pantry for more room to prep. A warm sunroom provides another space for a group of 6 to enjoy a meal while overlooking the grounds. This leads right into the formal dining room where all 22 guests can gather around the table in this thoughtfully designed space. ☆☆ LIVING, PATIO, GYM ☆☆ This nice open floor plan leads right into a flexible and elegant living room. Multiple groups can choose to gather in this space: unwind on the sofas by the fireplace, pick up a game of chess at the bistro set, or relax in the comfortable barrel chairs. A smart TV gives the option to sign in and stream any of your favorites together! This well-lit space is tastefully designed with both new furnishings and vintage finds to pull in its historic character. You'll also be able to connect to an indoor/outdoor sound system to be able to enjoy background tunes wherever you choose to gather! French doors lead you right out onto the brick patio where you can pull up a lounger and rest under the shady awning. This patio is also equipped with 2 outdoor dining tables as well as a gas grill for dining al fresco. A second sunroom also leads out to the patio. This sunroom is furnished as a gym space complete with rogue squat rack, dumbells, and Peloton bike. No need to skip your workout and enjoy beautiful views of the grounds while you do it! ☆☆ LIBRARY & GAME ROOM ☆☆ Right inside the grand front entrance here you'll find a convenient half bathroom with ornate original wallpaper. As you explore the entry and last wing of this first floor stop to take in unique original artwork in the halls. Enter "the library" a distinguished space of shelves lined with plenty of books, art, and board games. You'll also find here a record player bringing this space truly back to it's original 1920's roots. Off the library you'll find a full bathroom with fun vintage wallpaper and a full tub and shower. The bathroom also leads out to the "game room" another sophisticated space that steps back in time with a pool table and leather wingback chair to unwind. ☆☆ SECOND FLOOR ☆☆ Head up the stairs and you'll find a long hallway lined with 6 of the 9 total bedrooms. All bedrooms are furnished with 100% cotton linens from California Design Den and memory foam mattresses for a truly luxurious night's sleep. The first bedroom "Folly Cove" is furnished with 2 full beds and surrounded by plenty of windows for natural light. The "cranberry" walls are a nod to the estate's name and furnishings give a vintage vibe. A large closet and dresser provide plenty of space for suitcases to unpack. The next room on this floor, "Half Moon Beach Studio" is a yoga studio for those who want a place to truly retreat. This space is stocked with yoga mats, dumbbells, exercise bands, and mirrors to guide your practice. The full bathroom on this wing is a newly tiled space with bathtub and shower. Each bathroom is equipped with hair dryer and bath amenities (shampoo, conditioner, body wash). Our housekeeping staff provides a fresh set of towels on each bed. The next bedroom pulls from "Good Harbor Beach" just down the road. This cozy nautical space is furnished with a bunkbed with 2 full sized mattresses. A dresser with mirror also provides a place to unpack and get ready. "Plum Cove" is the next bedroom and the most spacious thus far. This space is fitted with a comfortable King bed as well as a desk set up with 2 monitors for a robust workspace. There are multiple closets with built in drawers to unpack and a full length mirror for getting ready. A decorative fireplace, ocean views, and dramatic red accent wall make this an unforgettable suite. This room also has an en-suite bathroom truly making it like a second primary suite. Step down into the newly tiled bathroom and you'll find a tub and shower along with traditional fixtures like pedestal sink and sconces. "Pavilion Beach Lounge" is a flexible room conveniently located in the middle of both wings. This vibrant green space provides another space to gather while also serving as an additional bedroom as the comfortable sofa pulls out to a queen bed. A stunning antique hutch from the 1600's houses a smart TV for guests to sit back and enjoy a movie night. This room has an en-suite vintage style full bathroom with separate stand up shower stall and tub. Another bedroom is also adjacent to this bathroom in a "jack and jill" style. The "Long Beach Bedroom" is fitted with a spacious King bed and serene coastal blues, greens, and rattan throughout. A nook with desk offers another remote workspace for the guest on "workcation". Closets are equipped with drawers and full length mirror so plenty of space to unpack and make yourself at home. ☆☆ PRIMARY SUITE ☆☆ The primary "Wingaersheek Beach Suite" has a wing of it's own with plenty of space for a bridal party or other events where guests would like to spread out and get ready. There are essentially 2 full bathrooms in "his and hers" style within this suite. The first bathroom has a large built in closet, vanity, steam shower, and bidet. Adjoining this is another bathroom with toilet, vanity, and shower/tub combo. Enter into the light and bright bedroom and you'll find large 4 poster plush king bed. This luxurious bedroom is furnished with a vanity to get ready, a dresser, and comfortable window seat. Step into the en-suite sitting room and you will be awestruck by the panoramic views of the surrounding grounds. A comfortable sectional and Smart TV make this room an exclusive retreat. ☆☆ THIRD FLOOR ☆☆ On the third floor you'll find 3 more spacious bedrooms for guests to claim as their own! A full bathroom is on this floor making it perfect for a full family to have a floor to themselves. "Niles Beach" Bedroom is a beautifully wallpapered space furnished with a comfortable king bed and with a desk for remote work. Inside the closet you'll find space to hang and unpack in the dresser. Don't miss the stunning ocean views outside your window and serene ocean scenes in the art as well. The next 2 bedrooms on this floor are "Jack and Jill style connected by a full bathroom. "Cressy's Beach" is another King bedroom with dramatic accent wall and four poster bed. Plenty of space in the dresser or large closet to unpack. The adjoining bathroom has a shower/tub combination and unique vintage fixtures fitting for the time period of the home. The final bedroom is not to be missed! "Breakwater room" is set to a beautiful deep sea green with original wallpaper kept on the ceiling. 2 twin beds make this a great space for kids or comfortable enough for 2 adults. Nautical accents like hanging oars and lighthouse lamps create a fun eclectic space here. A sitting nook in the corner makes this the perfect little escape! ☆☆ GROUNDS ☆☆ As if there wasn't enough room in this almost 9000 sq ft estate there are 22 acres of grounds to explore outside! Leisurely stroll through the stunning formal gardens enjoying the springtime wisteria and natural cranberry bog. You'll have your own large private pond with bridge and fine impressive granite moraines. Not to be missed is a private trail with direct access from the property to Gloucester's stunning waterfront. ★☆ Book Today & Let Us Take Care Of You at Cranberry Hill! ☆★ Guest access You'll have access to the entire property and grounds except carriage house and barn. Please remember that you're staying in a house, not a hotel. Treat the space with respect. If any problems arise, we will do our best to take action ASAP. Other things to note • Check-in is anytime after 4:00 PM • Check-out is 11:00 AM or earlier • No early check-in or late check out • Quiet hours are from 10:00 PM to 8:00 AM • We have a strict no events policy per city guidelines • There isn’t central ac but we do have window ac units seasonally available in bedrooms between memorial and labor day.

Cranberry Hill | 9 BR 22 Acre Estate | Sleeps 22

A spacious and fantastic home for your family or group of friends perfect for a relaxing vacation. Located just a short walk from Rockport's Front Beach with its soft sand and beautiful ocean views. You'll also be close to downtown Rockport with its array of shops, galleries, and restaurants. If you're up for it, Gloucester's dining spots and whale watching tours are just a short drive away. Plus, you're within walking distance to the commuter rail, offering easy access to Boston and other charm The space The entry floor hosts an open foyer, a living room, a fireside room, a proper dining room and an updated kitchen. All decorated to create a classic New England seaside experience. And - an added porch room with raised dining table and view outside. The second floor hosts 5 classic refinished wood floor bedrooms and two full bathrooms. There is also a reading cove - so comfy. The third floor has 4 bedrooms and a full bathroom. Also with refinished floors. OUTSIDE - There is a two-tier deck with swim spa, hot tub, fire pit, picnic table, outside chairs, a grill and - for chilly fall/winter - some space heaters. One of the decks is open to sunlight and the other covered by shade. Guest access All the house except the basement and a back storage space are yours. Other things to note * Ideal for family, friend vacation or work group retreats * Well stocked Kitchen * Plenty of Living, Dining, and Sleeping options for Everyone * 6-Car driveway parking * Swim Spa, Hot Tub, Firepit

Classic New England: Big Family Home; Spas|Garden

Grand Family Home, great for groups. Walk to Good Harbor and Long Beach, 2 king beds, large deck, outdoor shower and AC. The space Welcome to Aerie! Enjoy this grand gathering house with great flow and enough rooms for all the beach lovers in your life. The home is situated between two of Cape Ann's most coveted beaches, Long Beach and Good Harbor Beach. As an added bonus the home is a moment's walk to an ice cream stand and pizza shop. Beamed ceiling, paneled walls, and wood floors throughout provide period detail and create a traditional cottage vibe. The first floor includes an open concept kitchen and dining area, a bathroom with stand up shower, a large living room with lots of seating, and a cozy den with fireplace. Laundry is also located on this level. A separate fridge is available in the basement for guest use. There is a finished, enclosed 1st level porch washed with natural light that opens onto a large exterior patio perfect for outdoor grilling, dining and lounging. Out back of the house is an outdoor shower to get all that sand off from your beach day! The 2nd level features 8 bedrooms and another full bath. Two of the front bedrooms room have distant ocean views. The four central bedrooms have central air. The rest of the bedrooms cooled by window units. (Portable ac units are placed as of memorial weekend and removed in early October). Aerie is a perfect spot for your groups fall visit to Salem as well. We are close proximity via train or car! The name Aerie means an elevated, secluded dwelling and this home is just that. This near 100-year-old beach cottage is perched above Thatcher road making it a quick walk to local beaches. Items to note: -We leave enough toilet paper/paper towel to get your groups stay started. We will leave you the required city trash bags. Should you need more they can be purchased at any local grocery store. -All bed linens/bath, hand towels are included. Beach towels are NOT provided. -Bookings between end of June and Labor Day require a week's stay. Check in/out is Friday/Friday. -Please note that we do not allow large unruly parties at the property due to proximity of neighbors. Excess numbers of guests or visitors are not allowed. We take respectfulness for our neighbors very seriously. Violators will be asked to leave the property. If your group cannot adhere to this, please do not book. *Our cancellation policy is firm and we cannot honor requests for refunds outside our cancellation policy for reasons related to illness, accidents, weather, wedding cancellations or any other change of plans. We encourage guests to purchase an outside insurance policy to cover them should they need to cancel their booking. Thanks for your understanding! Guest access All areas of the home are open to guests minus the garage area. Other things to note While we hope you enjoy the property to its fullest we ask that you please respect our neighbors by keeping noise to a minimum. Large outdoor parties or events are prohibited on the property. Excess number of guests in the property is not allowed. Noise complaints after 10 pm quiet time will be forwarded to police. Should you violate this your reservation will be cancelled and you will be asked to leave. If your group cannot handle this we ask you not to book.

Aerie, 2 king beds, large space, AC, 2 beaches!

A unique private estate, rich in history and natural beauty. The home was the residence of Benjamin F. Butler, the colorful Civil War general and Massachusetts governor, still belonging to his descendants. Enjoy fifty-five rolling acres of meadows, forest, marshgrass and rocky granite shoreline, with a white-sand crescent beach, a flat mica beach. You will have use of the Main House (5BR) and the Maids Quarters (2BR), which is a separate, pivate residence, with a separate entrance. The space This charming home is nestled within a sprawling 55-acre estate established in the late 1800s, featuring a vibrant community of historic homes. The property boasts rolling, well-maintained walking paths that connect residents to various estate amenities, including two private beaches, a playground, and even a historic cemetery just across the road. Enjoy the serenity of the estate while remaining conveniently close to modern conveniences—a short drive takes you to local shops and an array of dining options in Gloucester and Rockport.

The Homestead: Elegant Victorian & Maids Quarters

The Edgemoor Estate, part of the @ZENDENESCAPES - Luxury collective (find us)! Your ultimate coastal escape awaits at this magnificent mansion on Eastern Point in Gloucester MA. Sleeps up to 32. Main House: 11 Bedrooms, 13 beds sleeps 26. CARRIAGE HOUSE sleeps up to 6. 8.5 Baths. Jacuzzi (365days), heated pool (seasonal) this estate is a rare and coveted find for families/retreats. Just 100 yards from the beach, the property combines breathtaking ocean views with a serene, private setting. The space Inside, you’ll find timeless elegance with soaring ceilings, grand windows flooding each room with natural light, and ample space for dining, entertaining, and relaxation. Recent renovations bring modern comfort, from a new heating system to 50+ new windows, and a whole-home generator, ensuring a flawless stay. The gourmet kitchen and updated bathrooms boast tasteful finishes that complement the mansion’s refined character, making every moment of your stay feel elevated. Outside, the property shines with its manicured grounds, heated saltwater pool (Summer), and jacuzzi, providing a luxurious oasis perfect for lounging and unwinding on sunny days. A separate guest house and yoga room (available for rent separately and coming soon!) offers additional privacy and convenience, while the pool area invites you to soak up the sun or take a refreshing swim, surrounded by landscaped gardens that add a touch of peace and privacy. Whether you’re gathering in the spacious living areas, savoring gourmet meals in the elegant dining room, or stepping out to explore the stunning beaches just steps away, this property offers an extraordinary setting for an unforgettable coastal retreat. Indulge in the timeless charm and ultimate luxury of Gloucester’s finest short-term rental—your private paradise awaits. Guest access Guests will have full access to the property. Carriage House can be rented separately with additional fee. Please inquire within. Other things to note MAIN HOUSE: Can host up to 26. Guests over 16 will be charged $50/person/night CARRIAGE HOUSE: Can host up to 6. Separate payment and does not come with Main House Automatically with bookking. *Due to capacity of the home at 32 people and the limitation of Airbnb at 16 total guests, Any reservations over 16 people will be charged a fee of $50/person per night for main house and that will be collected either via this platform or separately via credit card. Carriage house will be handled separately. POOL Pool will be open late spring until late fall. Please inquire as to whether the pool will be open on shoulder seasons. Its all weather dependent. CARRIAGE HOUSE 6 Person Capacity 1 Queen Downstairs with bathroom 1 Queen Upstairs with Kitchen, Bath, Living Room and Pullout Sofa (2 people) Available for rent separately. Extra cleaning, nightly rate and extra guest fees will apply. GARAGE Garage is not available for guests at this time, but there are plenty of parking spots onsite. SIMILAR TO AIRPLANE POLICIES - CHILDREN OVER 2 ARE CONSIDERED PAYING GUESTS.

The Edgemoor Estate: Pool-Jacuzzi-Beach-Sleeps 32

Family gatherings and family reunions. Make those family memories at this ultra contemporary take on a tree house. Original design based off the iconic Farnsworth house, updated with 10 Bed rooms of individual climate control atop of 20 acres of wildlife. Designer kitchen for the professional chef. Privacy that most movie stars long for. 5 min to beaches 10 min to Gloucester 20 min to historic Salem 45 min to Boston. Pesticide free landscaping Great location for family gatherings and reunions The space Almost a decade of design went into this property. It has the ability to stand out from the outside, yet blend in from the inside. The iconic Farnsworth design brings the forest into the first floor living room with floor to ceiling windows. Guests can expect deer to come up to the windows if avoid spooking them. At night the exterior flood lights illuminate the front lawn as the woodland creatures come out. The second floor provides an aerial view into the forest with equally impressive windows. Guests can expect complete silence and zen at the house. Best value for large gatherings of friends and familes. Salem is the best place to be in September and October. A quick drive or a few train stops away. This is the perfect house for a group or family. most hotels are booked out years in advance and no other houses can accommodate our size. Great holiday house for Halloween or long term stays. Prebooking tours welcome Guest access First floor master bedroom. The house leads directly to hundreds of acres of walking and biking trails Other things to note Summer is for the beaches, fall is for Salem and scenic drives, historic tours, winter is for family events and retreats. we provide the space. you provide the memories. Many of our guests are family reunions. Please keep in mind that this is an ultra modern design and has a much different feel to it than a standard traditional home.

Secluded 20 Acre 10BR ultra contemporary Retreat

☀ Sleeps up to 19 guests ☀Plenty of driveway parking ☀ Prime location on the Back Shore ~ 1 mile or 5min drive to Good Harbor Beach - beach gear included! ☀ Private pickleball and/or tennis court ☀ Ocean views on 3rd floor ☀ Sprawling lawn+multiple decks to enjoy ocean breezes ☀ Private au-pair suite perfect for an additional family ☀ Family friendly amenities included - toys, pack and play, booster ☀ Multiple living spaces to gather on first floor ☀ Hi-Speed WiFi and Smart TVs throughout The space Welcome to Bell View, a spacious, family‑friendly coastal getaway in Gloucester — just a five minute walk from the sparkling Atlantic and the beauty of the rocky coastline known as Bass Rocks. Welcome to Bell View, a spacious family home tucked away in Gloucester's coveted Back Shore neighborhood. This almost 5000 sq ft home was carefully crafted for groups to enjoy the 2 acres of rare space in this seaside community. Enjoy no shortage of living spaces from sun room, game room, to formal living and dining rooms. A private in-law suite with kitchenette makes this the perfect spot for groups looking for their own space. Conveniently just minutes to Rocky Neck, Bass Rocks Golf Club, and Good Harbor Beach. Perfect for families, friends, and groups, this home blends seaside New England charm with comfort and fun. 5 Min Drive to Good Harbor 5-10 Min Drive to Gloucester's Main Street (Beauport Hotel, Cruiseport, etc) 30 Min Drive to Salem Experience Bell View With Us & Learn More Below! ☆☆ FIRST IMPRESSION ☆☆ Nestled in the quant neighborhood of East Gloucester you'll pass Rocky Neck art colony on your way into this quiet street. The long driveway provides plenty of privacy as well as parking for multiple cars. ☆☆ FIRST FLOOR ☆☆ Inside, a one-of-a-kind waterfront scene, hand painted along the staircase by a local artist, greets you as you enter via the formal foyer. Pick your hangout spot from two comfortable living rooms, a game room with a ping-pong table, the sunroom, the cheerful and well equipped kitchen, the umbrellaed patio, or the multiple decks and porches. ☆☆ SECOND FLOOR☆☆ Head upstairs and you'll find a common full bathroom as well as a bedroom with 2 full beds and a bunkbed room. This floor also boasts 2 king suites each with en-suite bathrooms. One of these suites features a desk for remote work and the other has convenient laundry machines in the bathroom as well as a private balcony. ☆☆ THIRD FLOOR ☆☆ This bonus "loft style" floor is perfect for kids! Carpeting throughout makes it a safe place to play and there's plenty of room and toys to spread out. Four twin beds are comfortable for kids or adult guests! This floor also gets amazing ocean views. ☆☆ PRIVATE SUITE ☆☆ The "in-law suite" is located on the east wing of the house. Head up stairs to a cozy apartment - the perfect place for a family or couple to have their our private space! A sofa bed also pulls out to a full sized mattress to sleep 1 or 2 additional guests. A bistro set and kitchenette gives you the option of to have some nights in to yourself. Unwind in front of the smart TV or enjoy your own private balcony after a day of north shore exploring! ☆☆ OUTSIDE ☆☆ Set on a spacious lot with plenty of level lawn space, Bell View also boasts a tennis court with equipment to double as a pickleball court. The shed is contains all kinds of sports equipment and outdoor toys - perfect for guests of all ages. In addition, a slate patio in front and a wraparound deck in the back are delightful spots to gather and relax. Bell View is just a stone's throw from Bass Rocks on Gloucester's Back Shore where you can enjoy looking out at the scenic surf or a leisurely walk listening to the sounds of waves. It's about a mile to Niles Beach and 2 miles from the white sands and surf of Good Harbor Beach. The home is also about a mile to Rocky Neck, the oldest art colony in the U.S. and home to many galleries, shops and great restaurants. ★☆ Book Today & Let Us Take Care Of You at Bell View! ☆★ Guest access You'll have access to the entire property and grounds except the garage. Please remember that you're staying in a house, not a hotel. Treat the space with respect. If any problems arise, we will do our best to take action ASAP. Other things to note • Check-in is anytime after 4:00 PM • Check-out is 11:00 AM or earlier • No early check-in or late check out • Quiet hours is from 10:00 PM to 8:00 AM • Please note that the tennis/pickleball court is available for guest use during all daylight hours but there are not lights available for evening play so that we can be courteous neighbors.

Private Pickleball | Family Friendly | Sleep 18

Welcome to The Chillavista! A newly renovated oasis on the coast of historic Gloucester. Walkable to downtown, restaurants, beaches & parks! Highlights include: -Decks overlooking the ocean -Game Room with Arcade Machine, Classic Nintendo & beverage fridge -Lobster Pot w/ all the essentials -Kids playroom with books & toys -Phone Chargers -Fireplaces -Record Players -2 Fully stocked Kitchens -Board games -Grill (extra propane) Perfect for families or friend groups & Executive Off-sites! The space Each space has been curated with you in mind. Wifi porters so that you can tap or scan to get connected. You'll find remote controls for the TV, Fireplace, heat & AC. Comfortable beds and linens to make your stay as enjoyable as possible. Traveling with kids? Well we thought of that too. The kids can enjoy a dedicated play space just for them. In the Game Room you'll find a classic Nintendo, Pac Man, TV, beverage fridge and plenty of seating. Come see what else we have to offer at our traditional New England Two Family! Guest access You'll have private access to the entire two family home, also known as a duplex in other parts of the country (5 bedrooms, 4 full baths, 2 kitchens, 2 dining rooms, 3 living rooms, game room, 4 decks and bonus kids play nook). To get between the units you may use the front or side deck. This also includes five dedicated driveway parking spots (can fit 6 depending on size of vehicles) the front and backyard plus basement to utilize the 2 washers, 3 dryers & access beach chairs/outdoor games. Other things to note We have provided beach chairs, lawn/beach games, sand pails and other outdoor fun located in the basement. The City of Gloucester recently completed a coastal resilience project on the canal behind our home adding a seawall not shown in our aerial photos. We do have professional landscaping, snow removal and trash removal so you may see these folks helping us maintain our property during your stay. Our home is equipped with a whole home generator so you’ll never be without power while staying with us. This past winter storm dislodged a section of our fence! We are aware and are on the schedule to receive a new fence. Lastly, we’ve updated the railing on the 3rd floor which will differ from the photos you see (for the better 🙂).

Newly Renovated Ocean Escape

Welcome to your perfect Gloucester getaway! This completely renovated 5-bedroom, 3.5-bath home is located in the highly desirable East Gloucester neighborhood—ideal for families, remote workers, and beach lovers alike. The space Stylish East Gloucester Retreat | 5BR + Office | Walk to Marina & Good Harbor Beach Welcome to your dream coastal getaway in the heart of East Gloucester—just a 1-minute stroll to the marina and a 10-minute walk to iconic Good Harbor Beach. Perfect for families, remote workers, and groups, this fully renovated multi-level home blends modern luxury with classic New England charm. ✨ What You’ll Love Brand-new hardwood floors throughout Chef’s kitchen with quartz countertops, oversized island & stainless steel appliances Open-concept main level with kitchen, dining, living, laundry & powder room Finished basement with foosball, games & bonus lounge space Thoughtful layout across 4 levels to give everyone room to relax 🛏 Sleeping Arrangements 2nd Floor Master Suite: King bed + private en-suite bath Guest Room: King bed Guest Room: Queen bed Full shared bath 3rd Floor Guest Room: Queen bed Kids Room: Two Twin beds Separate Office for remote work Basement Finished lounge with games & foosball 🌊 Comfort & Amenities 3rd Floor: LG mini splits in each room for A/C 2nd Floor: Ceiling fans in every room, No A/C Main Floor & Basement: No A/C, but well-ventilated with cool coastal breezes Smart Honeywell heating system for year-round comfort In-home laundry High-speed WiFi 🚗 Things to Know Max 10 guests on property Driveway parking for up to 4 cars only NO PARTIES, NO EVENTS, NO LOUD MUSIC, Quiet Hours: 10pm-8pm 📍 Location Highlights 1-minute walk to East Gloucester Marina 10-minute walk to Good Harbor Beach Moments from downtown Gloucester: restaurants, shops, art galleries & more Whether it’s a summer family vacation, a fall coastal escape, or a work-from-anywhere retreat, this home offers the perfect blend of space, style, and unbeatable location on Cape Ann. Guest access Door Code Provided 10 Days Prior To Booking

Luxury 5BR Family Retreat | Walk to Beach & Town

Welcome to Tidebend, your next Gloucester escape! This stunning 6-bedroom, 2.5-bath home overlooks the picturesque Annisquam River and offers a unique blend of craftsmanship, comfort, and convenience. Thoughtful custom woodwork and built-ins throughout the home highlight exceptional quality while adding character and function to the living spaces. With six bedrooms and plenty of room to gather, Tidebend is an ideal fall getaway for families and larger groups looking to enjoy all that The space Spend your mornings on the inviting farmhouse-style front porch and soak in the peaceful water views from upstairs. Enjoy your evenings watching breathtaking sunsets. In the fall, the changing foliage and crisp coastal air make Tidebend an especially inviting retreat, offering a beautiful setting to relax after a day of exploring Gloucester. Located in a quiet neighborhood of Gloucester, Tidebend offers plenty of space for your family to enjoy this tranquil retreat. During the fall, guests can enjoy scenic drives, coastal walks, local events and festivals, fresh local seafood, charming shops, and the many seasonal activities throughout Gloucester and Cape Ann. Whether you're planning a family fall vacation, a weekend getaway with friends, or a peaceful autumn escape by the water, Tidebend provides the perfect home base for your Gloucester stay. Other things to note No smoking. No events or parties.

Tidebend: River Views and Gracious Comfort

Welcome To 61 Atlantic Rd in Gloucester, a pristine seaside home boasting stunning ocean views and located just a short 5 minute walk to Good Harbor Beach. Enjoy the front porch overlooking the Atlantic Ocean, incredible views of First Cove and Thatcher Island. Fabulous back yard with patio, bar, grill and outdoor shower. This home was built new in 2014. It has 3000 square feet of living space and parking for 6 cars. Very special location. Perfect for one or 2 families. The space Our guests will have access to beach chairs, beach towels, linens and towels. A fully appointed kitchen plus an outdoor gas grill. Free Wi-Fi and full cable channels. Sonos speakers for your enjoyment. We have a glider on the front porch and a table with seating for 8 overlooking the Atlantic Ocean. Patio in back has wicker furniture seating for 8 and bar seating for 8 also.

Luxurious 5 Bed Home Ocean View Walk Good Harbor

Welcome to the Rocky Neck and the Eastern Point neighborhoods. Steps away from one of the oldest working art colonies in the country which boasts 3 waterfront restaurants. Gloucester harbor, Niles Beach, and the Eastern Point Light House are a short walk away. Please note, the rental includes use of the cottage which is a large studio with a full bath and kitchen. The space The house was a summer retreat for the famous artist Childe Hassam. He was one of the first Impressionists to paint in Gloucester, and he did so for over twenty-nine years, starting in the early 1880s. Please note, the rental includes use of the cottage which is a large studio with a full bath and kitchen. Guest access Keys are left in a place easy for guests to retrieve and provide access.

Grapevine Rock House

Enjoy the natural beauty of the hillside forests, rocky monoliths, and the farm fields down to the marsh surrounding this getaway on 150 acre working equestrian estate. Easy access to hiking the Gloucester Watershed conservation lands, Wingaersheek Beach, Conomo Point, and downtown Essex Manchester, Gloucester, and Ipswich. Perfect for a corporate retreat or a family gathering. Located on Ebben Creek which overlooks iconic Choat Island. Perfect for boaters, can help with docking needs nearby. The space Ideal for both stays and events. Rambling estate house that feels like the English countryside or Napa Valley. Great floor plan that maximizes privacy. A Brief History of the Property The land on which the house stands was originally part of the Haskell property, belonging to a prominent local family whose roots trace back to the colonial era. The Haskells established a farmstead here, centered around a first-period colonial home and an exceptionally large barn that stood on the front lawn until the 1960s. The original house was lost to fire long before living memory, leaving only fragments of its story behind. In the mid-20th century, the property became the country retreat of a local man who turned the hill behind the house into a retreat for festivities. He built a dance hall and and invited bands to come and play jazz music. In the 1960s Mrs. Lothrop constructed the present house, continuing the site’s long tradition of habitation, but in a more modern mid-century, mission-style design. The property came into our family in the early 1980s and has been cherished ever since. While much has changed over the centuries, the land retains a sense of continuity—linking its colonial beginnings, its hospitality connections, and its present-day life as a place of gathering and retreat Guest access Enjoy the entire house (other than locked spaces) and the pool. Garage and barn are off-limits. Other things to note Well behaved dogs are welcome. 7 bathrooms not 4. For events Airbnb has a maximum occupancy cap of 16 people at any venue, which includes all guests and visitors. For larger events please message us directly. There is an extra fee for an event and also insurance.

Forest Lodge at Haskell Gove Estate

Discover the historic charm of Bayview, a stunning private estate once home to Civil War General Benjamin F. Butler. Spanning 55 acres of meadows, forest, and rocky shoreline, it features two pristine beaches: a white-sand crescent and a mica-strewn gem. Nestled in the quaint village of Annisquam, this peaceful family compound offers access to Plum Cove Beach, Halibut Point State Park, and vibrant Gloucester and Rockport. Indulge in fresh seafood, coastal beauty, and timeless serenity. The space Immerse yourself in the beauty of the seaside at this expansive coastal home, offering breathtaking views of the ocean from the grand living room and most upstairs bedrooms. Perfect for families or groups, the house comfortably sleeps up to 12 guests across six beautifully appointed bedrooms: Bedrooms 1 & 2: Luxurious king beds for ultimate comfort. Bedroom 3: A cozy queen bed. Bedrooms 4, 5 & 6: Each features two twin beds, ideal for flexibility and convenience. The heart of the home is the huge living room, designed for both relaxation and entertainment. Gather around the cozy fireplace, sink into plentiful seating, or enjoy movie nights on the large-screen TV. Step outside onto the spacious patio, where you can unwind in comfortable seating while soaking in panoramic views of rolling hills that lead to pristine beaches and the ocean beyond. For dining, the elegant dining room offers a touch of old-world charm, perfect for hosting memorable meals. The well-equipped galley kitchen provides everything you need to prepare anything from simple snacks to gourmet feasts. Your stay includes access to two private beaches and tennis courts overlooking Ipswich Bay, ensuring endless opportunities for recreation and relaxation. For adventure lovers, the property also provides two adult and two child kayaks, inviting you to explore the waters nearby. This is more than a vacation home—it’s your gateway to unforgettable coastal living. Other things to note All bedrooms are on the second floor.

Elegant Bayview Victorian Home; walk to beach

Welcome to Stay Cape Ann, where exceptional homes meet local hospitality. This property features: ✓ 2-min walk to Good Harbor Beach with ocean views from the deck, porch, and most bedrooms ✓ Spacious 5-bedroom home with 1 king, 2 queens, 2 fulls, and 5 twins ✓ Chef’s kitchen, large dining areas, and central AC ✓ Deck, covered porch, grill area, outdoor shower, and driveway parking for 4 cars See more photos, video tours, and local recommendations on IG @staycapeann. The space This expansive coastal home offers the ideal Good Harbor Beach stay, with ocean views, generous gathering spaces, and a location just a 2-minute walk from the sand. Designed for families and groups, the home combines beachside convenience with comfortable interiors, multiple outdoor spaces, and plenty of room to spread out. Enjoy morning coffee on the covered porch, beach days at Good Harbor, relaxed meals on the deck, and evenings gathering in the spacious living and dining areas. ★★★ HIGHLIGHTS ★★★ → 2-minute walk to Good Harbor Beach → Ocean views from the deck, porch, and most bedrooms → Spacious 5-bedroom layout with room for families and groups → Chef’s kitchen with high-end appliances → Large dining area plus kitchen island seating → Central AC, high-speed Wi-Fi, Smart TV, and laundry → Deck, covered porch, grill area, outdoor shower, and driveway parking for 4 vehicles ★★★ FIRST FLOOR ★★★ → Living Room: Smart TV and sectional couch for relaxing nights in → Dining Area: Large dining table plus kitchen island seating, ideal for shared meals → Chef’s Kitchen: Fully equipped with high-end appliances and cooking essentials → Laundry Area: Convenient first-floor laundry access → Bathroom: Full bath with modern shower → Deck: Water views and ample space for outdoor dining → Covered Porch: Multiple seating areas for morning coffee, reading, or relaxing after the beach ★★★ 2ND AND 3RD FLOORS ★★★ → Primary Suite: King bed, renovated en-suite bath, and stunning water views → Bedroom 2: Queen bed, crib, and water views → Bedroom 3: Queen bed with water views → Bedroom 4: Two full beds → Bunk Room: Sleeps 5 in twin beds, with desk and chair for added convenience → Bathroom: Full bath with modern finishes ★★★ OUTDOOR SPACE ★★★ → Deck: Ocean views with lounge and dining seating → Covered Porch: Private, peaceful setting with multiple places to sit → Landscaping: Lush surroundings for a relaxed coastal feel → Grill Area: Conveniently located at the back of the house → Outdoor Shower: Perfect after a day at the beach → Parking: Driveway fits up to 4 vehicles Guest access Guests will have access to the full home, deck, covered porch, grill area, outdoor shower, driveway parking, and laundry. Guests do not have access to two locked closets, the basement, or the garage. Please note that the entrance to the house is via the deck, which is accessed by a full set of stairs, as shown in the listing photos. Check-in details and any important house information will be sent prior to arrival. Other things to note The entrance to the home is accessed via the deck, which requires using a full set of stairs. Guests should review the listing photos and consider this if stairs or mobility are a concern. Guests do not have access to the basement, garage, or two locked closets. Traveling with little ones? A pack-and-play and high chair may be available upon request. Please let us know before your arrival if you would like either item so we can confirm availability and have it ready for your stay. Our Stay Cape Ann team lives and works locally. If you need recommendations for beaches, restaurants, fishing charters, or rainy-day activities, we're happy to help.

Stay at Good Harbor Beach

Welcome to the Gathering House - a special, spacious home - renovated in ‘21 to gather more than a dozen people – while affording pockets of peaceful rest. Enjoy the views of the ocean. Feel the sea breeze. Listen to the waves. Share meals in the gourmet kitchen or grill outdoors. Grab a beach chair & cooler and head to Loblolly Cove, Cape Hedge of Pebble Beach. This extraordinary home is ready to welcome you and your circle of love.. The space This is an "upside-down" house - designed to give you views from the ocean in the rooms where you spend the most time! The entrance is on the middle floor with 4 bedrooms (2 have queen beds and 2 have 2 x-long twin beds) and 2 full baths. Go upstairs to the gourmet kitchen that seats 18, the livingroom with.3 seating areas, the primary suite (with a king bed and deluxe bathroom), the "peace room" with a toy corner, the Juliette balcony out front and a spacious deck out back. On the lower level is a finished basement with a sitting area, 2 queen futons and an office area. The Gathering Home provides the perfect space for you to create precious memories! Guest access About 48 hours before your arrival, we will message you in AirBNB with an entry code for the doors. We are always available to answer questions and provide assistance!

Gather @ Ocean - Home Sleeps 14 w/ 3.5 baths

This is the vacation house you have been looking for! It’s perfectly located only a few steps from the private & secluded section of Coffins Beach. As well as a short walk to the world famous Wingearsheek Beach. The younger crowd will love the excitement of the public part of Wingaersheek beach, while the private access to Coffins Beach is unexcelled for that quiet relaxing time. Why have to make a choice when you can have them both? The space This is the vacation house you have been looking for! It’s perfectly located only a few steps from the private & secluded section of Coffins Beach. As well as a short walk to the world famous Wingearsheek Beach. The younger crowd will love the excitement of the public part of Wingaersheek beach, while the private access to Coffins Beach is unexcelled for that quiet relaxing time. Why have to make a choice when you can have them both? All within a 2-3 min minutes walk, less than 2/10th of a mile to the private neighborhood section of the beach called Coffins beach. Or 1/2 of a mile to the white sands of the public side of Wingaersheek Beach. This immaculate and graciously appointed home is the perfect destination for discerning beach lovers who want only the best in accommodation, sea & surf, at the same time having the secluded privacy you have been dreaming of. Housing accommodations are a perfect set-up for the extended family or share with the best friends. This location contains 3000 sq/ft. of housing for your enjoyment. This is one of the most private and secluded houses available in the area, as you will be quietly resting on 1.38 acres. Once you enter the private community by way of the guarded gate house and continue until Sleepy Hollow Pond you will turn on to your own private way and head up the driveway to the house, and you will immediately feel like you are on vacation and ready to enjoy your stay. All the while as it seems you are the only one around. You will be residing on your own 1.38 acres of private land. There are numerous outdoor custom built landscapes and a front patio to enjoy the beautiful weather and enjoy the wonderful privacy. As you walk-in the first floor entrance into the spacious custom tiled foyer/entrance, you will immediately feel the beach house charm! The first floor also contains an expansive open concept fully appointed eat-in gourmet kitchen featuring double built-in Jenn-Air ovens. The granite counters, custom cabinets, complete with Built-in counter blenders, and coffee grinder, pantry and stainless appliances completes this home so that it is the perfect place to be the ultimate beach home away from home. Produce your family’s favorite recipes or try some of the great local dining options, its all up to you. Beyond the 8 chair open concept, eat in kitchen, you can relax as you proceed thru to the spacious living room which contains the center-piece of the room, a beautiful custom stone built fireplace. Enjoy watching the 55” HDTV with the full surround system and music surround system (iPod friendly), or choose to relax in quietness, as the choice is yours. To your right you have two oversized custom French doors to the enormous and fully screened-in rear deck which has some spectacular water views over looking Sleepy Hollow Pond, which is a brackish pond teaming wide life. This is the prefect spot where you can relax on the outside deck furniture and sunbath privately instead of the beach if you prefer. As you continue around the first floor, there is the first of the three very nice bathrooms. For the more formal dining experience, you can always entertain in the Formal Dining room, if you prefer. You will also find the separate laundry area off the kitchen entrance/foyer. As you climb the stairs to the Lower Level. You will enter into the entertainment area which contains a large TV, and a spacious and comfy living room sets, and don’t forget you can always challenged each other at the 3-in-1 game table, with your choice of pool, ping pong and air hockey. Perhaps you prefer to play Xbox with your friends and family, and of course bring some family favorites, or sit at the beautiful Oak table and play table games or have a card tournament. It’s a great space while you’re not enjoying the beach. Additionally the sectionals do contain sleeping arrangements which can be used once the fun has ended! Once you are back on the main level and you climb the stairs to the second floor you will find the king sized master bedroom with cathedral ceilings It contains your own custom full-sized bathroom and another queen-size sofa set, and a large TV. The King size bed actually looks small in this space! There also is a huge second king size bed room, and an additional bedroom with Two Bunk beds set ups, one with pull-out trundle to round out the sleeping arrangements. The third full size custom bathroom is also located between the two bedrooms. In addition to the three bedrooms on the second floor, we also have a very large beautiful bedroom with a queen size bed in the loft over the garage, which gives you the added ability to have an another extra bedroom to fully round out this wonderful location. The house is air conditioned, if you prefer, or you can enjoy the sea-breeze air and open the numerous oversized Anderson windows. For those of you who need to always be connected, the house has WiFi, of course, but brings your cell phone as there is no landline at the house. Plenty of parking in the U- shaped driveway and lovely landscaping outside! Additionally, Gloucester is quickly becoming artwork-culturally friendly area. Take a ride to the local artwork shops found around Rocky Neck. Find a new treasure for your home to remember your trip or come every year if you prefer. More pictures and information available. Please make a request or make a suggestion. There is everything you would expect for a great ocean beach stay, located only 10-15 minutes drive to Gloucester harbor. Electric Beach/Golf cart provided with house. Once you experience this vacation house and locale, you will want to return for years to come. Start a new tradition and make a reservation today! New in 2013.. Exciting news, we are adding a Classic restored 1965 Pontiac GTO or a 1986 Tran Am WS-6 for rental during visiting guest stays. Enjoy the area even more in a Classic GTO or Trans Am. Please ask about rates and pictures if interested. NOTE: If you are looking for an additional house/property, Please view our beautiful sister-house (Homeaway Listing number: 951090 or VRBO Listing number: 391707 ) Located only 1/3' of a mile away, and located in the private section of the beach as well. Absolutely NO smoking or Pets allowed. For the safety and comfort of all current and future guests.

A Diamond In The Dunes

Step into your own slice of paradise with our newly renovated beachfront haven, perfectly perched along the captivating Long Beach in Rockport. Picture yourself waking up to the soothing sounds of waves and the mesmerizing sight of the ocean stretching out before you. With five cozy bedrooms accommodating up to 14 of your nearest and dearest, along with two sparkling bathrooms and a gleaming, fully equipped kitchen, this is the ultimate spot for unforgettable getaways with family and friends. The space Welcome to Driftwood Long Beach in Rockport, MA! Nestled along the pristine shores of Long Beach, our beach house invites you to indulge in the ultimate oceanfront retreat. With 5 bedrooms, 2 full baths, and ample space to comfortably sleep 14 guests, this coastal haven promises unforgettable moments with family and friends. Enjoy our spacious covered front deck over looking the Atlantic Ocean. The deck allows for comfortable lounging as well as outdoor dining for 6+. Linens and beach towels are included. In addition: Owners beach chairs, boogie boards, and beach toys are here for your enjoyment! Beach tents are available upon request (additional fees applied). Brand new (4) top of the line energy efficient split heat/ac. On site parking spot for 2 vehicles. Charges apply at gate ($60 per week/per car, $20 per car on weekends, $15 per car on weekdays). Additional vehicles street parking. Quiet hours are between 9pm-8am

Oceanfront Home Rockport

Family friendly 4+ bed, 4 bath home in the heart of Annisquam in Gloucester. In addition to the 4 bedrooms, there is a loft w/ 4 more twin beds. 4 outdoor decks w/ large lawn in addition to washer/dryer, AC and private beach access. The space Beautifully constructed, family-friendly 4 bedroom, 4 full bathroom home in the heart of Annisquam, one of the most desirable areas of Gloucester. In addition to the 4 bedrooms, there is a loft that can sleep 4 more. The basement of the house is an "in-law apartment" with its own bedroom, bathroom and semi-kitchenette (no stove). There is a gorgeous lawn with a hammock and plenty of room for lawn games. The house boasts 4 decks with the main one having outdoor seating for 12 and the top one with views of Ipswich Bay. The house has several split unit ACs, as well as a washer and dryer. The driveway can easily fit 4 cars. The property is a half mile away from the majestic Annisquam Lighthouse Beach-- a private, sandy beach, which you will have access to. It is also a stone's throw away from Diver's Rock, a smaller rocky beach, which looks out into Ipswich Bay with views of Crane's Beach, Newburyport and the coast of New Hampshire. Here you'll have easy access to swimming and great views of the sunset. The house is also just a 15 minute drive from Gloucester's two biggest and most famous public beaches-- Wingaersheek and Good Harbor. Annisquam Village is a short drive or walk away where jumping off its wooden footbridge is a perfect high tide activity. A short 10 minute drive will put you into downtown Gloucester where you will find an array of fine dining options as well as Main Street,which boasts dozens of shops and boutiques. If history is your thing, be sure to visit the Cape Ann Museum and the Gloucester Maritime Museum, both located in downtown Gloucester. Take a stroll along beautiful Stacy Boulevard where you will view the Outer Harbor and the open ocean beyond. See the historic Gloucester Fisherman Statue, which memorializes they who have gone down to the bottom of the sea in ships. Continue down the boulevard and cross the historic Cut Bridge where you'll find Stage Fort Park-- a scenic outcropping with incredible views of not only Gloucester water line but on a clear day of the Boston skyline. If art interests you, head over to the famous art colony of Rocky Neck where you find countless galleries as well as numerous restaurants right on the water. Continue north up 127 until you reach Rockport, where you can explore the dozens of shops, restaurants and ice cream parlors down Bearskin Neck and get a perfect view of the most painted building in the world-- Motif Number 1. Guest access Guests have access to entire house except for a few locked closets.

Walk to Lighthouse Beach | Annisquam Gloucester

Steps to Good Harbor Beach, 5 Bedrooms, Air Conditioning, Large Deck, Fire Pit The space Welcome to your very own summer beach home! Located across the street from the North Shore's best beach, Good Harbor Beach, this family home offers five bedrooms, two bathrooms and a separate living area downstairs. The grounds include parking for six cars, an outdoor entertaining/dinning area, and spacious fenced yard for the kids to run around. Perfect for a large group or family. Inside you will find comfortable furnishings and all the necessary items to make your stay enjoyable. Onsite amenities include but are not limited to: Wi-Fi, Washer and dryer, cable, fully stocked kitchen with dishes and cookware, two televisions and bunk bed set up for those traveling with kids. Don't forget the outside shower to get all that sand off after a day on the beach. The top floor features 2 bedrooms, a large open living area with dining room and kitchen and a full bath. All upper rooms have ductless AC units to keep nice and cool on those hot summer days. The living room, kitchen and dinning room are all open concept and lead out to the large deck overlooking the yard. The primary bedroom has a king bed and small private balcony offering views of the marsh. The second bedroom has bunk beds (twin over full). The downstairs has three bedrooms a full bath and second living room. The lower level generally stays cooler than the upstairs but window AC’s are provided in all of the bedrooms. the living room had a ductless wall unit. Two bedrooms feature queen size beds. The third bedroom is two twin beds. There is a pull out queen sleeper in the living room. The laundry (washer/dryer) is also located on this level. Aside from the accommodations, what will keep you coming back year after year, is the unbelievably short walk to Good Harbor beach. You can be on the beach in minutes and you'll welcome the short walk back after a relaxing day. PLEASE do not park on the right side of the house. (Grass side) *linens/towels are not provided. We do provide comforters/mattress and pillow covers. Please see the house manual for needed items. *pets are not permitted. Bookings between last week of June - Labor Day require a weeks stay. Check in/check out on Friday Other things to note Please do not park on the right side of the house (grass side). This is not our property. We do NOT provide linens or towels. Blankets/mattress protectors and pillow covers are provided. Please see the house manual for bed sizes/info.

Beachside at GoodHarbor, King bed, fire pit, AC

Enjoy unparalleled views from this clifftop house located between Good Harbor Beach and Long Beach. This 5-bedroom, 3.5-bath home is just a 5 minute walk from both beaches, and a short drive from both downtown Gloucester and Rockport. The space First Floor: * Large kitchen and dining area looking over the trees to Long beach and the ocean * Living room with couches, chairs, TV with AppleTV * Full bathroom and half bathroom * Washer and Dryer * Bedroom with Queen bed * Bedroom with Twin bed * Sun room Second Floor: * Primary bedroom with King bed, attached full bathroom, and sweeping southeast ocean views to Salt Island and beyond * Bedroom with Queen bed, eastern ocean views * Bedroom with two Twin beds * Full bathroom Outside areas: * Giant deck with grill, table, umbrella, chairs and unbeatable views of the ocean * Garden and grassy yard with lawn chairs and table * Parking in front of garage Guest access Guests will be able to use the entire first and second floors, but not the basement (which is unoccupied and used only for storage).

Clifftop Home in Gloucester

Entire Mansion in the most coveted neighborhood in Gloucester, with private backyard, Pool, 2 car garage in a quiet neighborhood, 3 min walk to waterfront, access to beaches, restaurants, bars and the best of everything New England - Gloucester have to offer. 4 Bedrooms, 4.5 Baths, sleeps 12, Master Suite with Jacuzzi. 10 min walk to Niles Beach, 10 mins scenic drive to Good Harbor beach. Private backyard deck with a pool, for family cookout and short walk to restaurants / bars and ice cream. The space Upon entering this exquisite residence and property situated on over two acres of landscaped privacy, this exceptional Georgian Colonial with fill your heart with warmth and visions of future family memories. The blend of Old World Charm and modern amenities creates a truly memorable living. Original features include beautiful Pine flooring, Formal Dining Room with stunning Arched Cabinetry, and Living Room just as impressive with a handsome fireplace flanked by French Doors leading to a granite patio. The kitchen is spacious with an eating area, Butler’s Pantry open to Family Room with French Doors to the deck overlooking the in-ground pool and yard, with a large deck, an outdoor dining table and Weber Grill. The Master Bedroom is delightful with his & her vanities, a spa tub, a tiled glass shower, and a walk-in closet. The four personalized guest bedrooms each offer a private ensuite bath with an optional rear staircase access. The grounds are beautifully landscaped. The Pool cleaning is scheduled weekly on Wednesday between 8 AM to 5PM time slot. When the maintenance people arrive, please vacate the pool immediately to allow maintenance. You are advised do not enter the pool for 24 hrs max after maintenance is complete. Feel free to check with the main individual - when it is advised to enter the pool, as the maintenance is customized. Guest access You have access to the entire grounds, which includes the Pool and Patio area, and the landscaped gardens. Other things to note The Pool cleaning is scheduled weekly on Wednesday between 8 AM to 5PM time slot. When the maintenance people arrive, please vacate the pool immediately to allow maintenance. You are advised do not enter the pool for 24 hrs max after maintenance is complete. Feel free to check with the main individual - when it is advised to enter the pool, as the maintenance is customized. Landscapers will be in the property on Thursday morning, or next day in case of rain.

Mansion in Gloucester with Pool

Enjoy a luxury experience at this centrally located beachfront home with sweeping water views of Gloucester Harbor.The house is located across from the Beauport Hotel and Pavilion Beach. The suites are located on the 1st, 2nd & 3rd floors with 4 decks, 2 full kitchens, 2 gas fireplace, 2 laundry, 2 full bath and 3 half baths. 4 spacious bedrooms: 2 with a king bed & the other 2 with 4 full beds. Ascend to the loft to enjoy specular ocean views & wet bar. *Multiple listings in the same building* The space This beautiful totally redesigned newly renovated building offers the Pavilion Beach Suite and the Birds Eye View Suite. The Birds eye view is located on the second and third floors and provides 2100 square feet +/- of luxury living. This suite offers a split-level floor plan filled with natural light from sunrise to sunsets allowing you to enjoy the amazing water views and boating activity. The main floor of the Birds Eye View Suite provides you with a Juliet balcony coming off your kitchen and living room area. Up the stairs, you’ll have access to the loft area. Here you’ll find a wet bar, seating area, 1/2 bath and a large deck with spectacular views of the ocean, Stacy Boulevard, the Beauport Hotel and beyond. This unit offers 2 large bedrooms, 1 full bathroom with a soaking tub, 2 half bathrooms, a full kitchen, a wet bar in the loft area, and water views from almost every window in the unit. Each bedroom has a tv, comfortable beds, down comforters, blackout blinds and a closet. The Birds Eye View Suite offers 2 large bedrooms, 1 full bathroom with a soaking tub, 2 half bathrooms, a full kitchen, a wet bar in the loft area, and water views from almost every window in the unit. There is also a TV in loft for a total of 4 HD TV. Guest access When you book the entire house, you’ll have access to the Pavilion Beach Suite and the Birds Eye View Suite. Both suites offer central air, a gas fireplace and Wi-Fi. The suites can also be booked separately. Be one of the first to stay in this new property. Other things to note When you reserve the entire home, you will have exclusive access to both the Pavilion Beach Suite and the Birds Eye View Suite, 4 decks, and 4 parking spaces. Please be advised that for safety and liability reasons, we do not allow any grills, fire pits, bong fires, or any gas or cooking devices on the decks, outdoor spaces, or anywhere on the premises of this property.

4 plus bedrms 5 baths- 3 level Beachfront House.

Imagine spending your days swimming from the private dock at high tide or exploring the sandy shoreline at low tide. Launch a kayak or paddleboard from the beach and glide across the water to nearby islands or Wingaersheek Beach for a day of sun, surf, and adventure. Nestled on over an acre of waterfront land, Annisquam Singing Pines is a historic retreat that offers stunning river views, ample outdoor space, and charming indoor comforts—all designed to create unforgettable vacation The space Experience a Classic Cape Ann Summer at Annisquam Singing Pines Originally built as the summer home of Governor Bates, Massachusetts’ governor at the turn of the 20th century, this beautifully updated home seamlessly blends historic character with modern amenities. With five bedrooms and space for up to 10 guests, this is the perfect destination for family gatherings, friend getaways, or a relaxing waterfront escape. Property Highlights: Expansive Waterfront Property – Private dock, beach access, and panoramic views Multiple Porches &amp; Outdoor Living Spaces – Screened-in and open-air options Renovated Kitchen (2023) – Fully equipped with modern appliances Historic Charm Meets Modern Comforts – Updated interiors with original character Prime Location – Easy access to Gloucester, Rockport, Salem, and Boston Parking – There is off-street parking for up to 6 cars. Other things to note 2,418 SF. No Smoking. No events or parties. No fire pits allowed.

Annisquam Singing Pines: riverfront splendor

Enjoy stunningly beautiful ocean views from all 3 decks at this quirky 1820 colonial house with easy access to local amenities. Only a 15-minute walk to quaint Rockport center; a 5-minute walk to Back Beach; 7-minute walk to Front Beach, a 2-minute walk to wooded trails circling pristine granite quarries; and 3/4 miles to the train station with regular 1-hour train service to Boston. Lots of sleeping space with 4 bedrooms and other sleeping spaces. Parking and high-speed wireless internet. The space Enjoy the sounds and sights of the beautiful Atlantic ocean and have deeded access to the water via a right of way. Circa 1820 period home with original features and modern amenities overlooking the ocean and Sandy Bay with beautiful views of the village day and night. Multiple decks to enjoy the ocean, wildlife, and boating activity. Steps to the village, shops, restaurants, woodland trails, and commuter rail. Please, no loud parties or events. Summer Rentals are from Saturday at 3 pm to 11 am Saturday morning. Four parking spaces next to the house and more free parking is available in nearby public parking. There is no central A/C, window a/c can be requested for an extra charge. The house is well insulated and well heated in the winter. There are plenty of windows and 4 patio doors providing a cool sea breeze. The 3rd floor has 2 ceiling fans. Internet TVs in the living room and kitchen. Pack'n Play, strollers, and high chair upon requests. A child bed available. There is a small basement apartment below the first-floor deck with a separate back road parking and entrance. Guest access Will provide the location of the key before arrival

Rockport Home with Beautiful Ocean Views

Your family will be close to everything when you stay at this centrally-located home. A 3 minute walk to Rockport's sandy Front Beach, as well as downtown cafes, restaurants and the historic Bearskin Neck. Once you've enjoyed what Rockport has to offer come back home for an evening of grilling and outside dining on the large back yard deck and relax in front of the fire pit. When you feel like spending a day in Boston, Salem or places in between, the Rockport commuter rail is a 5-min walk The space Our beautiful house is old and has many unique features. One we'd like you to be aware of is the staircase to the second floor has stairs which are narrow and a tad steep.

Home in Rockport

- `* ` Spacious home near Rockport’s Front Beach, perfect for families or groups of friends. ** Ample indoor and outdoor space for relaxation and activities. ** Short walk to the beach, shops, galleries, and restaurants in downtown Rockport. ** Easy access to Gloucester’s dining options and whale watching tours (short drive away). ** Convenient walking distance to the commuter rail for trips to Boston or other North Shore seaside towns like Salem. The space * 5 bedrooms, 2.5 bath rooms, multiple living rooms * Swim Spa, Hot Tub, Firepit * Well Equipped Kitchen * Plenty of Living, Dining, and Sleeping options for Everyone * 6-Car driveway parking Guest access Access code is provided for smooth checkin.

Experience Classic New England-walk to beach&shops

🌟Waterfront home overlooking Ipswich Bay in Annisquam 🌟Balcony with panoramic ocean views 🌟On a 55 rolling acre estate of meadows, forest, marsh grass and granite shoreline 🌟The estate has walking paths that connect residents to various estate amenities, including two private beaches, a playground, and tennis court 🌟Board games and beach essentials included (towels, chairs, and umbrella) 🌟Outdoor shower 🌟Indoor wood fireplace 🌟BBQ grill 🌟Small work desk 🌟In unit washer and dryer The space Escape with the entire family to this serene retreat, where tranquility meets breathtaking beauty: Location: ☆ 5-minute walk to a private white-sand crescent beach 🏖️ ☆ 5-minute walk to a private flat mica beach🏖️ ☆ 5-minute drive to The Cove Cafe ☕ ☆ 10-minute drive to Halibut Point State Park 🌳 ☆ 15-minute drive to downtown Gloucester (lots of shops/restaurants) 🦞 ☆ 15-minute drive to Bearskin Neck (lots of shops/restaurants) 🦞 🍽️ Kitchen and Dining: (fully renovated 2026) ☆ Fully stocked kitchen with cookware, dishes, toaster, microwave, drip coffee maker (with coffee and supplies), blender, stove kettle, and other essentials ☆ Dining room with a large table seating 6 people 🛋️ Living Room ☆ Indoor wood fireplace ☆ 2 comfortable couches and arm chair with ottoman ☆ Ocean views ☆ Hidden TV with streaming ☆ Small work desk 🛏️Bedrooms (one bedroom on the main level) 🔵Bedroom 1 (main level) ☆ King bed ☆ Beautiful ocean views ☆ Clothes storage 🟢Bedroom 2 (lower level) ☆ King bed ☆ Beautiful ocean views ☆ Clothes storage 🔵Bedroom 3 (lower level) ☆ 2 single beds ☆ Clothes storage 🔵Bedroom 4 (lower level) ☆ Queen bed ☆ Clothes storage 🟡Bedroom 5 (lower level) ☆ 1 bunk bed and 1 single bed ☆ Clothes storage 🚿Bathrooms ☆ Both bathrooms have a hairdryers ☆ Bathroom essentials included ☆ Main level bathroom has a step in shower ☆ Lower level bathroom has a shower/tub combo 🌻Outdoor Living ☆ Balcony with panoramic ocean views, outdoor dining set, sun loungers and extra seating ☆ BBQ grill (gas and grill equipment included) ☆ Spacious yard around the house ☆ Outdoor games available ☆ Walkable to 2 beaches, a playground, and tennis court (first come first serve basis) Guest access The only spaces off limits are the attic and the storage area under the house. 🔑 Guest Access ☆ The entire home and grounds are yours ☆ We leave the door unlocked before check in with a key inside for guests to use during their stay. ☆ There is a spare key in a lockbox in case of emergencies or lost keys ☆ The beach and tennis courts are shared with other homes on the Bayview Estate - all related to one another. ☆ You will receive a text with a link to Breezeway digital guidebook which contains helpful info for the home as well as food/local recommendations for Gloucester 🚙Parking ☆ Private driveway can comfortably fit 2-3 cars ☆ Note that the house is on a dead end side street Other things to note Private beach access just a hundred yards away, which is shared with other families on this private compound. 🍼 Baby & Family-Friendly Amenities included ☆ Pack ’n play/Travel crib ☆ High chair ☆ Children’s dinnerware ☆ Kids games, books, and toys

Panoramic Ocean View; walk to private beach

Nestled in a private section of Wingaersheek Beach, this bright Gloucester vacation rental home is a tranquil escape for your upcoming ocean getaway. Offering 5 bedrooms, 2 bathrooms, and 2,500 square feet of beautifully appointed living space, this magnificent residence is perfect for families or a group of friends out for a rejuvenating beach retreat. Sip coffee by the wood-burning stove each morning, followed by a relaxing walk to the beach for a sun-filled day along the shore! The space Massachusetts Tax ID: C0836064320 | Open Layout | Interior Coastal Views | Access to Coffins Beach  Bedroom 1: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Bedroom 4: Queen Bed | Bedroom 5: Twin Bed w/ Twin Trundle | Living Room: Sleeper Sofa  INDOOR LIVING: Open concept, wall-to-wall windows, skylights, modern furnishings, formal dining table, 2 living rooms, wood-burning stove, multiple cable TVs, surround sound, Sonos music system, ample natural light, contemporary decor, unique fixtures, pop of color OUTDOOR LIVING: Wraparound porch, ocean views, river & dunes views, private beach access KITCHEN: Fully equipped, top-of-the-line appliances, stainless steel finishes, large kitchen island, dual ovens, 2 dishwashers, drip & single-service Keurig coffee makers, cooking basics, dishware & flatware GENERAL: Free WiFi, linens/towels, air conditioning, first aid kit, hairdryer, in-unit washer & dryer FAQ: Access only by stairs, 1 external security camera (facing out) PARKING: Driveway (5-6 vehicles) Guest access Guests will have access to the entire property Other things to note - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - The property requires stairs to access - Your safety matters. This property features 1 exterior security camera located on the exterior, facing outward toward the parking area. It does not look into any interior spaces. The camera records video when activated by motion - You will have access to Coffins Beach which is a 2-3 minute walk from the property and is easily accessible from Wyoma/Bungalow Road

Elegant Gloucester Beach Getaway with Ocean Views!

Andrews Point Ocean Home The space This historic waterfront home offers a spectacular setting for your next extended family vacation or group getaway. Located at the northern end of Rockport in the highly desirable neighborhood known as “The Avenues,” this spacious two-story retreat combines classic New England character with sweeping ocean views.  Inside, you'll find several inviting gathering spaces, including a bright sunroom with ocean views and comfortable living areas throughout the home. Beautiful decorative stone fireplaces add distinctive architectural character and historic charm. A well-equipped full kitchen makes it easy to prepare meals for the whole group, while the generous layout provides plenty of space to relax and reconnect.  Outside, the expansive grassy backyard meets the shoreline, where a slate patio at the water’s edge offers a perfect place to enjoy the coastal scenery.  What’s nearby: Kayakers and confident swimmers can access the water directly from the backyard, with additional launching spots just down the street. The historic Atlantic Path, located directly in front of the home, provides a scenic coastal walk past Sea Rocks and toward Cathedral Avenue.  The charming seaside town of Rockport is just three miles away, offering restaurants, shops, galleries, museums, and performances at the Shalin Liu Performance Center. Back Beach, Front Beach, and Old Garden Beach are all within four miles for easy beach days. Things to know: The fireplaces are non-operational Free WiFi Full kitchen Gas grill A crib, high chair, Pack-N-Play, changing table, and booster seat are all provided The family dogs are welcome to join you here Front door access ramp for guests with limited mobility Guest access Your keys are in the lockbox located on the stair post at the side door, to the right of the driveway. Check-in is at 4pm and checkout is at 10am.  If early check-in or late checkout are available for your dates, you'll receive an email or SMS offer. The home is being prepared between 10am and 4pm for incoming guests. Other things to note Complimentary start-up amenities include toilet paper, paper towels, shampoo, conditioner, trash bags, dishwasher pods, sponge, dish soap, laundry soap, and hand soap. You're welcome to purchase additional supplies as needed during your stay.  All bedding, sheets, and towel sets are provided, with additional linens and towels available in the home.

Sweeping 5BR Oceanfront Dog Friendly

Book today with this discounted off-season rate! Celebrate your family in this spacious and serene waterfront home overlooking Essex Bay. This historic home was built in 1894 by Boston Restauranteur Jacob Wirth; his family enjoyed it as their summer home. You now have the rare opportunity to enjoy this fabulous home on Essex Bay with your family & friends. The Town of Essex provides public access to a beach, dock, and mooring rentals. ❤️👏🏻❤️🙏🏻 The space This lovely and spacious home offers spectacular ocean views from most rooms. It was built in 1894 by Jacob Wirth, one of Boston’s renowned restauranteurs, as his family’s summer home. This exceptional and loved home has had extensive renovations over the years. We have just completed renovations of an incredible chef’s kitchen, opening the kitchen to the dining room with full ocean views in the front of the home. We continued renovations with an outdoor grill, stone patio, outdoor shower, a bar with a service window to the patio, and a screened-in sun porch. The entire home has been painted in a pristine white, allowing the sun to shine into the home, bouncing off its walls, and inviting its visitors to come out and play on the beach! In addition, we painted the second-level floors to give the home an updated beachy-chic feel. This beach house is spacious, 5,500 square feet. It has five bedrooms and 2 1/2 baths. There is a sizeable newly renovated 600-square-foot screened-in sun porch off the first floor. The sunny front porch offers another 400 square feet and has retractable screens on all sides as well! The first-floor level has 9-foot ceilings throughout. The new large modern chef’s kitchen will be a joy to cook in with a Wolf six-burner with griddle gas stove, electric oven, microwave, and plenty of refrigerator space. In addition, there is a bar with a wine refrigerator and abundant storage space. There are two dining areas. The main dining room is surrounded by views of the bay in the front of the home, and the outdoor kitchen on the stone patio is entered via new glass French doors from the sitting room. There is a full, as well as a half bath on this level. The living room has a gas fireplace for cooler evenings, perfect for sitting by the fire with a glass of wine and an excellent reading book! The second floor continues with its 9-foot ceilings throughout, and it has five bedrooms. There is a large balcony, off one of the bedrooms, with breathtaking ocean views. The primary bedroom is 300 square feet with double closets and an ocean view with spectacular sunrises! There are two Jack and Jill style connecting bedrooms, each with a closet and gable window alcove. Finally, there is a west-facing bedroom with a sunset view. Come stay with us and enjoy the magic of Conomo Point! Guest access The third floor is the owners suite, which will not be included in the rental. Other things to note The housekeeping fee includes a seventy-nine dollar charge for accidental damage protection insurance which covers up to three thousand dollars. This only covers your stay and damage must be filed prior to your departure to be covered, so please let us know of any accidents when they occur so we can put a claim in promptly. This insurance covers anything damaged accidentally, a broken dish or glass, wine spilled on a rug etc. It does not cover negligence, damage to house by cars, or pet damage. The rental rate on Airbnb includes monies required for tight tank service. The tight tank has an alarm which will go off as the tank approaches the full level. It is usually emptied every 2 weeks. Reducing water usage is always strongly encouraged on the point.

Quintessential Oceanfront - The Jacob Wirth House

Sea La Vie is a contemporary beach house steps from Good Harbor Beach, ideal for family getaways and wedding season stays. Enjoy ocean views, modern amenities, and a spacious deck for outdoor gatherings. Close to restaurants and amenities for added convenience. Perfect for creating lasting memories by the sea. The space Steps from Good Harbor beach. This vacation rental offers 4 bedrooms and 3 bathrooms with 3,000 square feet of spacious living perfect for relaxation and socializing. First floor: - Living room has high ceilings equipped, ceiling fan with an 85 inch flat screen TV, L shape couch that converts to a sleeper sofa, and wood fireplace to cozy up next to while sipping your morning coffee. - Dining area comfortably seats 8, ideal for family meals and gatherings. - Fully equipped kitchen with beautiful water views, top of the line appliances, large kitchen island, dual oven, dishwasher, coffee maker, air fryer, microwave, dishware, flatware and everything you need to prepare delicious meals. From the kitchen there is an entrance to the back deck with a gas grill and seating for outdoor dining. - First bedroom has a queen bed that boast direct access to the back deck, offering a tranquil retreat. - Second bedroom is a charming kids' room with bunk beds, ensuring a cozy and fun space for the little ones. - Full bathroom with a stand up shower, washer and dryer. - Extra bed/sleeper sofa is available in the living room. Second floor: - Master king suite is on the second floor. Features a king size bed, water views, private den/office with a balcony, 50 inch TV, couch, full bathroom with a stand up shower equipped w/messaging water heads, double vanity, powder area, bidet. Third Floor: - Junior suite has a king sized bed, skylights with ensuite bathroom and stand up shower. Free amenities: - Free wifi - Extra blankets, pillows, linens, towels - Air conditioning throughout the house - In unit laundry machines - Blow dryer - Iron/ Iron board - Board games - Reading material - Off street parking for two cars - Plenty of closet and storage space throughout the house - Beach chairs, toys, cart, wagon, umbrellas Guest access You have access to the entire house. Gas grill, Beach chairs and accessories. Other things to note The local area offers numerous activities and amenities within a short distance by car or on foot from the house. We will provide a comprehensive list of attractions, dining options, and shopping opportunities in and around Gloucester, Ma.

“Sea La Vie” 4Bed / 3Bath Walk to Good Harbor

Portside at Front Beach is newly renovated 3-family home in a historic building in the heart of Downtown Rockport. Complete with three decks with ocean views, a spacious backyard and central air conditioning it is the perfect place to bring your group. The space Great for families traveling together or groups who want to spread out. Portside offers four queen bedrooms and four bathrooms over four floors. With three units that can each be rented separately, you can take your pick of where to stay (see Portside Walkabout, Portside Glimpse, and Portside Overlook). Each apartment has a kitchen, laundry and a full bathroom for each of the bedrooms. Walk right into the ground floor one-bedroom apartment with a slider to the patio and easy access to the spacious yard. One the second floor you'll find an almost identical apartment with a small deck where you can catch a glimpse of the Atlantic Ocean. The top unit on the third and fourth floors has two bedrooms and two bathrooms. Take your pick of decks to relax on while you overlook downtown Rockport and Front Beach. Other things to note When you're ready for an adventure just walk a few hundred yards to beautiful Front Beach or to the shops, galleries and restaurants of downtown Rockport and Bearskin Neck. No smoking. No events or parties.

4 Floors, 3 decks in the heart of Rockport

Welcome to your serene coastal getaway! This stylish, family-friendly rental house offers breathtaking ocean views and is just steps away from the beach. Enjoy spacious living areas, modern amenities, and a cozy atmosphere ideal for relaxation. With a fully equipped kitchen, comfortable bedrooms, and a charming outdoor space to enjoy the sea breeze, this is your perfect escape for creating lasting memories with loved ones. Book now and experience the ultimate beachside retreat!

Gloucester Ocean View Home

Sea Breeze offers a spacious, newly renovated, 4 bedroom escape, that smiles down upon Good Harbor beach. Take in the refreshing salt air breezes while enjoying the solitude of being situated at the end of a quiet cul de sac. A short 3-5 minute drive gets you into the Good Harbor parking lot or take a 20 minute walk instead. Close-by downtown Gloucester is teeming with spectacular restaurants and activities for the whole family. The space Home includes a large kitchen with all the appliances/essentials including a coffee/tea station. It also boasts a bright, well-lit breakfast nook/work area that looks-out on the backyard and ocean. Dining area with a table to seat 6 comfortably. A spacious, comfortable living room with a streaming smart TV. Four bedrooms – Bedrooms 1-3 are located on the second level and all have great views of Good Harbor Beach. Bedroom #1 has a full-sized bed; Bedroom #2 has a queen-sized bed: and Bedroom #3 is the Master bedroom with a king bed and full bathroom. Bedrooms 1-2 share a full-bath on the same floor. Bedroom #4 is located in the finished basement and has a full-sized bed. Air-Conditioning/heating: Each bedroom (including the basement bedroom), and the entire living area on the first floor, are equipped with highly-efficient, Mitsubishi mini-splits to bring custom temperatures (warmth or coolness) to guests at Sea Breeze. Large, back deck off dining area (with ocean views) for eating and sunning is surrounded by a partially fenced-in yard for a pet or young children to play within an earshot. The home provides all bedding and linens, a washer/dryer, fully stocked bathroom and shower needs, 5G internet, a charcoal grill and weekly trash and recycling pickup. Guest access With the exception of a closet on the main level and a storage room in the basement (both locked), guests have access to the entire house.

Ocean views! Welcome to Sea Breeze! Winter rates!

Longview House The space Visit the charming coastal town of Gloucester, MA, and choose this beautiful home as the perfect retreat for your next vacation. Conveniently located just an 8-minute walk from the Commuter Rail, shops, restaurants, downtown area, beaches, and the Boulevard, you'll have easy access to all that Gloucester has to offer. Take schooner and lighthouse tours ( to see 5 iconic lighthouses -- one of which they can see from the house) or visit the many beaches in the area (get there early). Beyond the property, Gloucester beckons with a variety of activities for all interests. From beachcombing and whale watching to shopping and dining at local restaurants, there's something for everyone. Explore the nearby towns of Essex and Manchester-By-The-Sea, or take a trip to Salem to discover its fascinating history. Whether you're seeking a relaxing coastal getaway or an action-packed adventure, this house serves as the ideal base for your Gloucester escapades.  Step inside this lovely home and enjoy a range of amenities, including ocean views, a jetted tub and central AC. The spacious deck and patio provide the ideal setting for outdoor gatherings, while the gas grill is perfect for summer barbecues. Challenge your friends and family to a game of cornhole or just sit back and breathe in the ocean air. Inside, you'll find a well-equipped kitchen with modern appliances, a washer/dryer for convenience, and comfortable living spaces to relax in after a day of exploring.  With its dog-friendly policy, this house ensures that every member of the family can join in on the fun. Whether you're lounging on the deck with your furry friend by your side or heading out for a day of sailing or paddleboarding, you'll create unforgettable memories in this coastal gem. Book your stay now and immerse yourself in the beauty and charm of Gloucester!  Things to Know Guest access You'll enter using a keypad code on the smart lock. Enter your code and wait for the green light - that means the code is accepted. Then rotate the deadbolt away from the door opening. If the light flashes red, the code may have been entered incorrectly; wait 5 seconds for the lock to reset and try again.  When you leave, press the lock button and rotate the deadbolt toward the door opening. Note that this lock does not engage automatically when the door closes, so please make sure it's secured before you go.  Standard check-in is 4pm and checkout is 10am. If early check-in or late checkout is available for your dates, you'll receive an offer via email or SMS. Other things to note The home comes stocked with complimentary start-up amenities: toilet paper, paper towels, shampoo, conditioner, trash bags, dishwasher pods, dish soap, laundry soap, sponge, and hand soap. You'll need to purchase any additional supplies you use during your stay.  All linens, bedding, and towel sets are provided. Additional linens and towels are available in the home if you need them.  Trash is picked up weekly - please place all trash in the designated receptacles outside.  There's an alarm panel in the front foyer that is not currently active. If it starts chirping, simply open the panel and press the 1/Off button to silence it.

4BR beautiful home walk to town, boulevard & train

Stunning sunsets, a parade of boats going by, a charming marina and a beach brimming with natural beauty—these are the sights you’ll behold at this year-round waterfront home built to maximize its spectacular maritime views. The modern yet cozy house features a balcony overlooking the water. An open floor plan allows for maximum water views from the kitchen, dining and living areas thanks to an expanse of windows across the entire first floor. Registration #: C0176131070 The space Relax in a rocking chair with a book or spend the day in the fresh air by taking advantage of the private dock just 50 feet away from the house. Swim at high tide or embark on a nature walk on the firm mud flats during low tide, when tidepools capture sea creatures that delight all ages. When hunger strikes, fire up the gas grill and gather around the table on the patio, which also features water views, or cook in the fully equipped kitchen outfitted with a gas stove and basic pantry supplies. The house offers two bedrooms with queen-size beds, water views, and balcony access, plus a bedroom with two twin beds on the top floor. There is also a laundry area and large bathroom on the top floor that the three upstairs bedrooms share. Downstairs, there’s a bedroom with a full-size bed located next to the bathroom, and two couches in the living room open to queen-size beds. The downstairs shower features a handicap seat and grab bars. Other things to note **PLEASE NOTE** We are booked for summer 2023, but we hope to host you at some other point in the year! Also, if bringing a dog, please make sure your pet fee has been added to your total before requesting to book. Thanks!!

Swim in Summer, Ski in Winter—Waterfront Sunsets!

Just steps to the beautiful, white sand of Good Harbor Beach in Gloucester, MA. Spectacular views, in-door hot tub with slider to a large deck with grill and multiple sitting areas. Balcony off of the master bedroom. Comfortable 4 Bedroom, 3 Bath Home. The space Location, Location, Location! Get ready to do some serious relaxing at this beautiful and comfortable, 4 bedroom house just steps from the private end of Good Harbor Beach. Open and airy living space with spectacular views of the beach, modern kitchen with all the amenities, large dining area for 8 guests, cozy seating for TV watching around the fireplace. Indoo hot tub and shower area with slider onto large, sunny deck (multiple sitting/dining areas.) Master bedroom features a good-sized balcony with a fantastic view of the beach. These photos truly speak for themselves, you will never want to leave.Newly installed mini-splits. Guest access Guests will have access to the entire home. there is a basement apartment that rents separately. This space is on a lower level and feels very separate but you will pass their entrance on the way to your house. Other things to note We are very close to all the super markets. There are also whale watches, water-taxis, art museums, local cinemas and great restaurants all within a five minute drive. The house is available as a "winter rental" from Mid Sep-end May (full term required - please inquire about monthly rate & terms).

Steps to Good Harbor Beach

Magical first-period farmhouse near the sea and convenient to all Cape Ann has to offer! Perched among rolling green hills in the Essex countryside. Also, an 8 person hot tub & outdoor shower situated near the glorious herb & flower gardens for your relaxation.   ***Sorry no weddings or large parties allowed per town ordinance.  Small gatherings are usually fine but please detail the use of property before booking***

Rustic Lux Farm House with Simplistic Elegance

This 4-bedroom house is in a prime location & has EVERYTHING you need for an amazing vacation to Gloucester, MA! • 13-minute drive to Wingaersheek Beach • 10-minute drive to Downtown Main Street in Gloucester • 2 inflatable Paddleboards • 4 Kayaks Available! • Outdoor Patio w/ Oceanfront Views • Large Jenga set • Fully Stocked Kitchen • Multiple Outdoor Spaces: Balcony/Deck • Family Friendly- Pack n Play & High Chair • Beach Essentials: Chairs, Umbrellas, Life Vests, Towels The space Nestled in the charming coastal town of Gloucester, our exquisite home offers the perfect year-round retreat with breathtaking panoramic water views. With 4 bedrooms and 3 bathrooms, our spacious sanctuary accommodates up to 12 guests, providing ample space for relaxation and adventure. Enjoy direct river and ocean access right from your own dock, where you can even catch striped bass right off the water! You can kayak or paddleboard right over to Wingearsheek Beach, making for a perfect day of exploration. The stunning bluestone patio offers an ideal spot for soaking up the sun. Conveniently located, our home is a gateway to explore the area's natural beauty, vibrant attractions, and delightful dining options. Experience the ultimate coastal getaway at our beautiful waterfront haven. MAIN SPACES OF THE HOME: – 4 BEDROOMS & 3 BATHROOMS – BEDROOM 1: * King-sized Bed * Twin-sized Trundle Bed * Smart TV * Ceiling Fan w/ Light * Wooden Drawer w/ Mirror * Nightstand and Lamps * End-of-the Bed Chairs * Ensuite Bathroom w/ Walk-in shower BEDROOM 2: * Full-sized Bed * Smart TV * Nightstand and Lamps * Ceiling Fan w/ Light * Plush Chair BEDROOM 3: * Full-sized Bed * Twin-sized Bed * Smart TV * Ceiling Fan w/ Light * Nightstand and Lamps BEDROOM 4: * Full-sized Sleeper Sofa * Smart TV * Plush Chair – 3 BATHROOMS – * Upper Level : 2 Full Bathrooms * Main Level: 1 Full Bathroom – CHEF’S KITCHEN – * Fully Stocked * High-end Stainless Appliances * Large Fridge * Nespresso Coffee Maker * Tons of Cabinetry & Large Island * Expansive Windows – LIVING ROOM– * 55" Smart TV * Large Plush Sofa & Chairs * Hanging Egg Chair * Open Floor Concept directing to the Kitchen & Dining Area * Expansive Windows –LOFT LIVING SPACE– * Smart TV * Plush Chair * Full-sized Sleeper Sofa Guest access The guest has access to the entire home minus the locked cleaners closet. Other things to note State Tax Number: C0484721070 Check-in is at 4pm Check-out is at 10am *NO PETS ALLOWED - No parties allowed—violations may result in immediate termination of the stay. We aim to maintain a respectful environment for our neighbors. - Parking in the driveway for 3 cars max. Street parking allowed: NO - Guests must be 21 years or older to book this property. GUEST VERIFICATION: To help ensure a smooth and secure stay for all guests, the primary guest listed on the reservation may be asked to complete a quick verification process within 48 hours of booking, depending on the platform used to book the reservation. Prior to check-in, guests may also be asked to sign a Rental Agreement that includes agreeing to our rental terms and conditions and, on certain booking platforms, providing a valid government-issued ID and matching credit card before arrival. Included with your booking is our damage waiver coverage, which helps protect against accidental, self-reported damage during your stay when reported prior to check-out. C0484721070 ROC-21038977-003

Oceanfront Dock Escape ~ Kayaks & Paddleboards

On the ocean’s edge, this peaceful, rustic retreat, once a 1920s girls camp, now a beloved family home, is the perfect seaside escape. Relax on the spacious screened porch overlooking one of the few East Coast spots where the sun sets over the water. Walk down the lawn to swim or explore tide pools. Equipped with two kitchens, two baths, three double rooms, a bunk room, and a single bedroom. Located in scenic Gloucester, near fresh seafood, art galleries, and farm stands.

Ocean Front Cottage

.Relaxing private location .4 beds 2 baths with full kitchen/pans/Dishwasher/Wash/Dryer.Renovated organic design integrates historic architecture with modern touches.If you come for hikes, beach/music/food scene, you will enjoy the Rocky Neck District .The unique home has 4 bedrooms /4 Queen Beds. Speedy WIFI .Parking is up a steep narrow drive . NO trucks or XL SUVs. 2 cars max. Note* Kitchen and LR are upstairs.There are stairs. Contact owner for questions re:parking or limited mobility. The space Coffee ,tea, provided. International guests are welcome. You do NOT have to bring your own sheets and towels. You do NOT have to wash the provided beach towels, bath towels and bed linens when you depart. Guest access The kitchen ,living room and dining area and 2 bedrooms are on the upper level. Upstairs there are 2 bedrooms and 1 bath, Downstairs There are 2 Bedrooms and 1 Bath. The driveway is steep and narrow and cannot accommodate TRUCKS or large SUVs .Parking is best for 2 vehicles .If vehicles are not oversize, may be possible for 3 cars. Please message for details. No visitor vehicles or delivery vehicles are allowed on the property. Other things to note Cyclists welcome! checkout the 5 mile Atlantic ocean loop with incredible views of the twin lighthouses of Thatcher Island or and visit the old quarry at Halibut Point State Park. Washer and Dryer available at the house for your use. Beach towels and extra blankets provided.

Rocky Neck Retreat

A private 2 acre retreat with relaxing and stunning panoramic views in all seasons. The house is the perfect set-up for the extended family or share with a second family. Everyone in your group, in every age level, will love being only minutes away from some of the best beaches, activities, history, and food in New England! And, all of this is only 45 minutes from Boston without “Cape traffic” -- that’s why we fell in love with this home and with Gloucester. The space **If you want to see a very detailed professional video tour of the home, please go to youtube and search for "Retreat at Rust Island" or "Retreat at Rust Island Gloucester, Massachusetts" to see our new 2026 Video Tour. We recently completed a full upgrade and modernization of the kitchen. In addition, we just completed a massive landscape project, which includes outdoor patios with stunning views and a 8,000+ sq ft of lawn perfect for fun and games, outdoor gatherings, and sunbathing. Finally, we just redid all decks, which are now modern steel cable railing. Feel free to ask for more details. Welcome to Gloucester, America’s oldest seaport! This two acre, family-friendly, contemporary private retreat on Gloucester’s Rust Island offers 4 Bedrooms with stunning panoramic views of dozens of acres of beautiful marshes, tidal pools, conservation land, and the Jones River, which flows into the Annisquam River and Ipswich Bay. Surrounded by birch groves and nestled among fine landscaping, this peaceful home offers luxury vacation living only a short drive to several of the best beaches in New England, as well as historic Gloucester Harbor. Once you enter the driveway and proceed up to the house, you will immediately feel like you are on vacation. Gloucester, Massachusetts has made a lot of news in recent years: the movie ‘CODA’ – based and filmed in Gloucester – won 3 Oscars at the Academy Awards including Best Picture. In addition, Gloucester served as a primary filming location for the Apple TV+ award-winning comedy-horror series Widow's Bay. And, Travel + Leisure recently named Gloucester one of the best places to live on the East Coast and previously ranked Gloucester’s Good Harbor Beach one of the best beaches in the United States! USA Today recently ranked Good Harbor Beach in Gloucester as one of the best beaches in the Northeast. CNN recently included Gloucester in the list of “15 of America’s best small towns and cities.” Come see why everyone loves Gloucester. This home is a bird lovers paradise. The house is the perfect set-up for the extended family or share with a second family. Please feel free to contact us with any questions about the home or special requests -- we will do whatever we can to be helpful! A substantial modernization was completed a couple of years ago. All 3 bathrooms were modernized (including the spa-like master bathroom), and the home had new paint and styling throughout. All bedrooms feature brand new hotel-quality linens and bath towels. You won’t be disappointed. Feel free to email us with any questions. This spacious home features large windows that invite the extraordinary view indoors. The spacious and open floor plan includes a large living room with high ceilings and a fireplace (and flat screen television), and an ample dining area (and outdoor decks). The home’s four bedrooms include a gracious cathedral ceiling master bedroom with King bed and en suite bathroom with soaking tub and separate shower. A second bedroom on the first floor sleeps three, and an additional baby crib is also available. A full bathroom with shower/tub is adjacent. Two additional bedrooms (one queen bed; two twin beds) and a large bathroom on the second floor offer privacy. The first floor of the home is wheelchair accessible. Please contact the host for more details regarding the property. The entire house is air conditioned. Or, if you prefer, you can enjoy the peaceful breeze air and open the two sets of screened Anderson gliding doors (decks are off the dining room and master bedroom). The home has gorgeous panoramic views of water (during high tides) and beautiful marshes and conservation land. There are plenty of spots nearby to launch kayaks (please contact us for details). Wingaersheek Beach and Good Harbor Beach – both of which are considered among the best beaches in New England are within a 10-minute drive. Several other smaller beaches are equally close to the property. Guest access Access to the home is provided without a cumbersome lock box or key exchange. Instead, you will choose a 5 digit code, and and the electronic lock to the home will be programmed work your code for the duration of your stay. Other things to note Please note that during summer (peak), we require 7 night rentals beginning and ending on a Saturday. We are a small family business and want the house to be rented out each peak week. I hope you understand! RULES: We have had dozens of amazing guests, partially because we are totally upfront on the house rules in advance (please do not book this home if it will not be a good fit for your group). This is our family vacation home, so we ask that you treat it as you would treat your own! :) We have a reasonable set of house rules designed to respect our neighbors, protect our property, and ensure a safe, enjoyable stay for all guests. The primary renter will be provided and required to sign (within 24 hours of booking) a strictly worded Short-Term Rental Agreement covering important topics such as noise, occupancy limits, smoking, cleanliness, and property care. A photo ID (scan) and the full names of all occupants are required prior to check-in — this is a requirement of our insurance carrier and is not negotiable. Please note that the host uses exterior security cameras to monitor activity around the property (never inside) for safety and compliance. ADDITIONAL HOUSE RULES: - No parties, events, or large gatherings - No smoking, vaping, or marijuana use anywhere on the property (indoors or outdoors) - No drug use of any kind - No alcohol consumption by guests under 21 - No pets of any kind - Quiet hours observed 10:00 PM – 7:00 AM (please respect our neighbors) - Maximum occupancy limited to the number stated in your reservation - Primary renter must be 30 years or older to book and present during the stay - No firearms, fireworks, candles, or hazardous materials - See Short-Term Rental Agreement for other rules Thank you for partnering with us to maintain a peaceful environment and protect our shared investment — we truly appreciate your cooperation!

Premium 2-Acre Retreat - Panoramic Marsh Views

Enjoy the sights and charm of Rockport from this inviting home, perfectly located just a few blocks from downtown shopping, restaurants, galleries, and sandy beaches. With plenty of room for family and friends, this property offers a fresh, comfortable interior and an ideal blend of convenience and relaxation with plenty of space for everyone to gather or unwind. Front Beach and Rockport's center are about 0.7 miles away. Commuter rail to Boston/Salem is about 0.5 miles away. The space The first floor features an open kitchen and family room, a dining room, and a separate den—providing space for everyone to gather or unwind. A full bath with a standalone shower, plus a laundry room with a washer/dryer combo, add to the convenience. Upstairs, you’ll find four bedrooms and two full bathrooms, offering ample space for guests. The basement provides an additional hangout area, perfect for games, movies, or quiet time. A three-season room extends from the family room, creating a light-filled space for reading, relaxing, or entertaining. Outdoor space includes a covered front porch, a private back deck, and a large backyard flanked by beautiful gardens—ideal for outdoor dining or lazy afternoons. Additional features include off-street parking for four cars and a location that puts Rockport’s best just a short stroll away. Guest access Entire Home Other things to note Beach chairs, coolers, beach towels provided.

The Rockport Retreat-walk to beaches and downtown

"The Sea Vagabond House is an expanded 1932 summer cottage, with spectacular views of the ocean waves, with the tidal Saratoga Creek offering a mesmerizing and changing scenes from inside and outside this charming vacation home. The home sleeps eight comfortably in beds. Each level offers a full bathroom with a bathtub/shower. There are plenty of bath towels and beach towels for each guest. "Comfortable, clean and close to the beach, we will return." The space First floor has two bedrooms, one with two twin beds and on with a full bed. There is a full bath, living room and a small kitchen. There is a deck with seating off the kitchen. Second floor has a living room with sofa bed, office, bedroom with queen bed, full bathroom, large dinning area with sink, coffee maker, and toaster oven. Other things to note We are pet friendly, with a 2 dog limit. Pet fee for one dog is $150. An additional $50 for second dog. The house has a basement apartment with a year round tenant. There is a separate entrance and no access to the main house from the apartment.

Sea Vagabond - Watch the waves, stroll to the sand

Gorgeous house in Rockport, steps to beach, town, train, Shalin Liu performance center! Stroll to the beach in 5 minutes, or to the shops and restaurants of Bearskin Neck in less than 10 minutes. Luxurious 3rd floor master suite features a spa-like bathroom - fully equipped kitchen, cozy living area with 50” flat-screen TV, air conditioning, beautiful outdoor space with 2 patios and gas grill. Come enjoy everything Cape Ann has to offer while enjoying luxury accommodations. The space Welcome aboard Kingsport! Step inside and enjoy the home's nautical ship theme. Prepare a meal in the Galley - and ring the bell when dinner's ready. Eat in the kitchen surrounded by windows with an atrium ceiling. Each bedroom has a unique personality, starting with the Captain's quarters - the luxury 3rd floor suite with a king bed and spa-like bathroom. The Admiral's quarters with its elegant surroundings and queen bed; the Skipper's quarters with its lively decor, full bed, and twin trundle underneath. Or hang out in the Pirate's Den, which sleeps 4 in twin bunk beds, and features a gorgeous custom mural. The living quarters feature a 50" flat screen TV, and a separate nook with a table for eating, playing games or tackling a puzzle. Built in cabinets include a selection of books, games and puzzles for you to enjoy. The outdoor space is quiet and shady, featuring two patios - one with table and 6 chairs for eating or hanging out with a cocktail. The other has a comfy seating arrangement with loveseat and two chairs. Lounge in the hammock, listening to the birds and overlooking mill brook, or hang out in the bonus garage room, with a ping pong table, and a full supply of beach toys/chairs and beach cart for the short walk to Front Beach. Guest access Bedrooms are on 2nd and 3rd floor of an older home - space may not be suited for those with limited mobility

Kingsport

From its waterfront perch, this vacation rental home overlooks Rockport's picturesque Pigeon Cove harbor and has spectacular, unobstructed views of Sandy Bay. The location of the home is ideal, away from all the hustle of town, but within a 10-15 minute walk to everything you might want, including Front Beach, restaurants, galleries and shops and the world class Shalin Liu Performing Arts Center. The space Enjoy the water views from the deck, porch, and patio that grace each level of the home or from just about every room. You'll enjoy nature's show, the ebb and flow of the tide, with the quiet passing of the lobster boats and their omnipresent gull followers. The living room, with sliders to the wraparound farmers porch, is open to the dining area and kitchen beyond. This is the perfect place to watch the sunrise (if you choose), from any of the decks or waterfront yard complete with a large fire pit. The granite kitchen has stainless appliances and stylish new cabinets. The main floor has two bedrooms, one queen with water views and another double bedroom. There is also a full bath with a tub and shower on this level. The second floor is the primary queen suite with a sitting area, flat screen TV and sliders to its own deck with those amazing views. Air conditioning will keep you cool, even on the hottest summer days. The bathroom is separated with a sink and toilet in a separate room and another sink outside in the main room for easy access. There is a bonus living and sleeping area on the lower level with a queen bed, double futon and flat screen TV as well as an oversized bath with a shower and laundry room. Sliders lead to the patio and spacious yard, and waterfront fire pit. Come and enjoy your little slice of waterfront heaven at Sunrise on the Cove. Please note that this is a waterfront property; younger children should be supervised at all times. Guest access Guests will have use of the entire home. Other things to note Parking for 6 cars. Dogs allowed. No smoking. No events or parties.

Sunrise on the Cove: Unparalleled Views!

Rare opportunity to acquire a fully renovated 3-family property in a highly desirable Gloucester location, just minutes from Good Harbor Beach and offering beautiful ocean views. The property combines strong rental fundamentals with the lifestyle appeal of one of the North Shore’s most sought-after coastal markets. The property has been thoughtfully renovated throughout, featuring updated kitchens and bathrooms, modern finishes, in-unit laundry, and two dedicated parking spaces. The flexible three-family configuration provides multiple income streams and makes the property attractive for both long-term rental and seasonal/vacation rental strategies. With its proximity to Good Harbor Beach, Gloucester’s restaurants, harbor, and downtown amenities, the property is well positioned to benefit from strong demand from both year-round tenants and summer visitors. The property also offers excellent potential for an Airbnb/short-term rental strategy, subject to applicable City of Gloucester regulations and permitting requirements. A major component of the investment opportunity is the separate 368R Main Street lot, located directly behind the property. This additional parcel provides meaningful future upside and could potentially support an ADU, additional residential unit, or other development concept, subject to zoning, permitting, utilities, and site requirements. Please reach out for private showings.

366 Main St Gloucester, Massachusetts

$152,024

Annual Revenue

Investment Value Over Time