Experience the Difference: Professionally Managed by iTrip Annapolis The space Family Rental only! This brand new custom home was built with stunning views of the Chesapeake Bay and all the bells and whistles, including a large private pool (open late April-end of Oct), hot tub (available year round) and game room on a semi-private beach. The four-season screened-in porch naturally stays warm in the winter from the sun and cools from the bay breeze with the windows open. The home is a perfect retreat for one or more large families traveling together on a private resort-like getaway. Upon entering the home, you will be wowed by the fully-loaded great room, complete with a flatscreen TV, electric fireplace, designer furniture and views of the waterfront landscape. The gourmet kitchen has luxury appliances, a breakfast bar, a dining table for 8 and high-end stainless-steel appliances. Before heading upstairs, check out the private office, which doubles as another bedroom with a Queen sleeper sofa, located off the main entryway. The home has two ensuite bedrooms: one on the main floor, with its own sliding door to the rear deck, and the other on the 2nd floor, with its own private office and sitting room. There are two additional bedrooms on the 2nd floor which share a bathroom and a bunk room on the lower level. All the bedrooms have views of the backyard and the Bay. Also located on the lower level is a decked-out game room (Pop-a-shot basketball, shuffleboard, ping pong, foosball table, and a card table) and full bath. Head outside to the furnished patio, complete with a hot tub and custom pool. Then make your way down to the beach. There's plenty of parking and a keyless front entry. Located in Tracy's Landing, this home is wonderful for families and friends looking to hunker down in the luxurious resort-like atmosphere. You’ll leave this place feeling completely rejuvenated! Come see for yourself! *Inquire about multi-day discounts for 5+ days SLEEPING ARRANGEMENTS 5 BR / 4.5 BA / Sleeps: Main Floor Suite: -King Bed -Private Bathroom with Double Vanity, large soaking tub and shower -Flatscreen TV -Private waterfront patio Main Floor Office/Bedroom -Queen Sleeper Sofa -Half bath on main floor and shared full bath in the 2nd floor hall 2nd Floor Suite: -King Bed -Private En Suite Bathroom with tub/shower and double vanity -Private sitting room with lounge chair and desk -Flatscreen TV -Water views 2nd Floor King Bedroom: -King bed -Flatscreen TV -Water views -Shared full bath in the Hall 2nd Floor Twin Bedroom: -Two Twin beds -Water views -Shared full bath in the Hall Lower Level Bunk Room -2 sets of bunks (4 Twin beds) -Shared full bath in the Hall HIGHLIGHTS: -Private Heated Pool and hot tub (Pool Closed end of Oct-late April - hot tub available year round) -Furnished screened-in porch -Chaise pool-side lounge chairs -Firepit -Games: Pop-a-shot basketball, Foosball, Ping-pong, Shuffleboard, Card table -Kayaks (7) and life jackets (available May-Nov) -BBQ Gas grill (propane tank provided) -Spacious open kitchen Breakfast bar seating for 3 -Dining room table seats 6-8 -High Speed Internet and WiFi -Multiple flatscreen Internet-based TV's throughout the home -Luxury linens, complimentary toiletries Starter Kit, and boutique-level service -Coffee pot + Keurig -Parking for multiple cars/SUVs in driveway -Washer & dryer located inside the home -Dogs allowed with $150 non-refundable fee per pet paid prior to checkin. -Keyless entry. Drive straight to your rental home and enter the front door with an electronic lock code. Property Distance to: -Annapolis – 23 miles -Washington, DC – 34 miles -Baltimore - 49 miles -Tysons, VA – 50 miles *Amenity & Supplies starter pack: coffee, sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid. * All beds are ready made for you with freshly-laundered sheets & towels. House Rules: No smoking or parties Must be 25+ to rent, with an adult present at all times For your security, we have one door camera facing the outside of the home and a noise decibel monitor that is compliant with the law. Check-in: 4:00 PM, Check-out: 11:00 AM Other things to note Please note that we may collect additional information from you after confirming your booking (usually an email address) in order to comply with local regulations and to provide the best possible experience. Regulatory Information STR00744 Registration Details 816441

LUXE Waterfront Retreat w Pool, Hot Tub, Game Den

Covered Porch w/ Mounted Fans & Speakers | Furnished Office w/ 2 Desks & Printer | 3 Mi to Beach | 19 Mi to Annapolis Your next holiday or corporate retreat awaits at ‘Heaven Sent.’ There’s plenty of room for work and play at this Deale vacation rental, which features modern perks like stainless steel appliances, 2 covered outdoor spaces with a large yard, and an office space for any emergency emails. Boat rentals and dockside drinks are just a short walk from this 5-bedroom, 3.5-bath home. The space STR-00959  SLEEPING ARRANGEMENTS - Bedroom 1: 1 queen bed - Bedroom 2: 1 full bed, 1 twin bed - Bedroom 3: 1 queen bed - Bedroom 4: 1 queen bed - Bedroom 5: 1 full bed - Bonus Room: 1 twin daybed w/ 1 twin trundle  INDOOR LIVING - Smart TVs, board games - Electric fireplace - Desk workspaces, printer - Dining table, breakfast bars - En-suite bathrooms  OUTDOOR LIVING - Private yard, marina & bay views - Covered patio, covered porch - Picnic table, grill, swing, outdoor fans, outdoor speakers  KITCHEN - Stove/oven, refrigerator, dishwasher, microwave - Dishware/flatware, cooking basics - Drip & Keurig coffee makers w/ coffee, slow cooker, toaster, ice maker, garbage disposal - Trash bags & paper towels  GENERAL - Free WiFi - Central heating & A/C, ceiling fans - Washer/dryer, laundry detergent, iron/board, hangers - Linens/towels, complimentary toiletries, hair dryer  FAQ - Quiet hours (9:00 PM-7:00 AM)  ACCESSIBILITY - Stairs required - 2-story home - Bedrooms/full bathroom on 1st floor  PARKING - Driveway (3 vehicles) Guest access Guests will have access to the entire property via self check-in 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 - NOTE: Please observe quiet hours from 9:00 PM to 7:00 AM ADDITIONAL INFORMATION - This single-story home requires using an exterior staircase to enter but features bedrooms and a full bathroom on the 1st floor Registration Details 000959

Water-View Deale Home: Walk to Marina, Restaurants

Chesapeake Bay waterfront home, cozy, comfortable, spacious and clean. Enjoy the panoramic roof terrace, dock with sun-platform and waterfront jacuzzi. Discover local adventure, seafood, dock-bars and historic towns. Connect with nature, celebrate and enjoy life with friends and family. This is your 'home-away-from-home' on the Chesapeake Bay Look forward to your visit! :) THE DWL FAMILY The space waterfront - 6 bedroom (3 full water view / 2 partial water view / 1 interior) - newly remodeled - roof terrace -private pier - beach 2min walk- hot tub - rustic modern interior - library - art collection - apple tv - bar - bluetooth stereo - caterer ready kitchen - large family and lounge spaces - ample parking - great community.. Guest access waterfront fun + many local attractions.. sailing, fishing, crabbing, hiking, cycling, dock bars, restaurants, yacht club, beaches ! Other things to note Events are not permitted. We take pride in being a well managed and professionally operated lodge! The property manager has provided amazing support and coordination for 100s of guests over the years. Special features include: Roof terrace with awe inspiring panoramic views. Large double lot offers privacy. Hot tub with waterfront view. 30' dock with platform. Close by, 'sharktooth' beach! short distance to Annapolis and DC. Registration Details 000089

The Driftwood Lodge - Chesapeake Bay Waterfront

Chesapeake Paradise House-Stunning 6+br4ba Wtrfrnt

Large, comfortable home is made for family and friends to get together (up to 15 guests). Your morning walk or jog is out the front door to the boardwalk or beach. Walk across the street for restaurants, ice cream, daily wine tastings, an organic market, yoga, spas, local art, antiques and a friendly hometown coffee shop. About an hour from DC, Baltimore & Northern Virginia, it is located 5 to 10 minutes from popular local wedding and event venues. The space New waterfront home with huge rooftop deck with both covered and open areas; balconies on all floor. Beautiful view of the Chesapeake Bay. All floors accessible by elevator. First floor is entry; second has 4 of 5 bedrooms; third floor is large open space on main level with dining, fully equipped kitchen and lounging area with tv; fifth floor has rooftop bedroom, covered eating area, grill and rooftop deck with fabulous view. Great for entertaining or lounging with friends or family. Fast wifi, cable tv. Just steps away from the beach, pier, and boardwalk in North Beach. Guest access The entire house is accessible, minus three locked closets. The elevator is useful for moving luggage and groceries, but stairs should be used for usual travel between floors. Guests who have trouble with stairs of course can use the elevator as needed. Bedroom most accessible by elevator has walk in shower. Wide hallways throughout. Other things to note Per Airbnb terms of service, we cannot allow parties or events until further notice.

Bayfront Home with Amazing Rooftop Deck!

New full home renovation with gourmet kitchen, wide open floor plan, multiple guests rooms, and a bunk room that accommodates 12. An inviting space that welcomes any couple or a large extended family. This home sits with only three other homes on a private peninsula and has water access on both sides. It is conveniently located less than an hour from DC and Baltimore on the west coast of the Bay (no need to cross the Bay Bridge). The space Enjoy the 2nd floor primary bedroom, and first floor great room, each with a view across a one mile stretch of the West River at the mouth of the Bay that is met by undeveloped Smithsonian land, and views of sunrises and sunsets to remember for a lifetime. The 2nd floor bunk room, and first floor front guest room, each look out to a newly laid sod lawn ideal for corn hole and kart wheels, and which touches the waters edge where there are kayaks and paddle boards, dock for endless hours of fishing, and a private elevated which offers a fire pit for cooler evenings as you watch the sunset. The inside of this inviting home has comfortable touches that welcome you from the minute you enter through the front door. Soft whites and warm wood throughout the home provide a clean, yet cozy aesthetic. The first floor has a private guest room with a queen bed, a full bath, a large mud room space to accommodate every garment and all your gear. The balance of this generous first floor is consumed by a wide open floor plan and windows to bring the view and light into this inclusive yet plentiful space which contains a gourmet kitchen, complete with an Aga stove with induction cook top, coffee maker, microwave, french door refrigerator/freezer and more cabinet space than could ever be fully utilized. Immediately opposing this kitchen space is a dining room table which accommodates 8 and room for multiple high chairs and additional seating. The entire front end of this first floor is a great room embraced by windows on all sides, a sunrise or sunset will never be missed while relaxing in this space which has a working fireplace, generous television with access to all your favorite channels, as well as a space for an alternative “kids” eating table, which doubles as the perfect table for cards and board games and accompanied by a full bench seat for onlookers! Finally, for all those adventurous children, a crafty play space has been created under the stair well which occupies hours of fun on those rainy days. The second floor includes: a full laundry room; the primary bedroom with a dedicated desk with extra monitor/TV and en-suite bathroom; a guest room with a queen bed; a second guest room with a queen bed and en suite bath; a shared full bathroom with double sinks and two shower stalls; and a deluxe bunkroom with 4 twin beds, 4 full beds, kids books, and a TV. The home is fully equipped for small kids as we have three of our own. The water on the dock side provides hours of family fun with multiples floats available for your use, paddle boards, kayaks (including one child kayak), life-vests (required for all boating activities), and deck with seating for adult onlookers. We have lots of board games, coloring books, and other indoor activities when you need some time inside. The home is close to many hiking and beach opportunities, restaurants, antique shops, fishing charters, Annapolis, and much much more! Please see the guestbook for more information. Guest access Guests are able to access all parts of the home and the lot. It is imperative that guests do not enter the neighbors' property, including their lawns, docks, and water access. Other things to note There is only parking for 4 cars and no street parking is available. The road cannot be blocked at any time. Registration Details 000394

Waterfront Sanctuary only 50 Min. From DC/Balt.

Waterfront- 5-bedroom house with dock in charming North Beach Experience an unforgettable vacation in this newly listed waterfront 5-bedroom house. This beautiful property offers plenty of space for guests to unwind and relax. The house comfortably sleeps 16 with most bedrooms offering en-suite bathrooms. The private dock offers the best sunsets views in North Beach. Fish off the pier or just sit, relax and bask in the fresh air of the Chesapeake Bay. Registration Details 000972

Waterfront- 5-Bedroom House

De-stress, Reset and Heal at our stunning, newly-constructed 3-story waterfront Zen Sunset Retreat (ZSR), with tons of amenities to ensure a delightful stay. Breathe deeply, and Heal from pressures of modern life. Enjoy our serene, sun-filled respite, with holistic self-care options on premise. Explore nature, fish/crab from the pier. Reserve on-prem sunset massages, guided yoga/ sound, Chef-led Cooking or Mixology Classes. RSVP 2 wks & additional fee. ZSR provides the PEACE; you do YOU! The space The Zen Sunset Retreat features an open-concept Living Room / Kitchen, 4 Bedrooms and 3.5 baths. The "fourth bedroom" comprises the whole third floor - a 700 square foot multi-purpose loft for yoga, meditation, entertainment/karaoke; and/or a fourth bedroom with its full-sized futon and full bath. The base configuration accommodates 4 bedrooms for up to 8 Guests. Beyond 8 Guests, there will be additional $50/Guest/ night. The optional 5th bedroom/ Office with Murphy bed accommodates 2 additional guests, and can be made available for additional fee of $100/night. This bedroom is on 2d floor and features dedicated full bathroom, walkout balcony facing unobstructed sunset view. Outside you will enjoy 3 balconies, all with stunning views of the Sunset over the West River, and the 100' ZSR pier. The house is ecologically powered by solar energy. The pier is dedicated to ZSR and has step down for small crafts, paddleboat, kayaks, fishing & crabbing. 4 life vests will be provided. Water depth is 4-5 ft depending on tide. Chalk Point marina is walking distance for larger boats. Church camp trails, other piers are marked as private property. Please respect private property signage rules. Fishing on pier: free for <16 yrs year round and 1st & 2d Sat in Jun for older than 16. Other days, MD license is required . Live Bait at Royal Farm gas station. Parking: ZSR driveway can fit up to 10 cars. Be advised, there is NO parking on either side of main road in front of peninsula. Upon booking you are confirming your agreement to the following Liability Waiver- You understand that swimming and the use of paddleboat, kayaks is at your own risk and that special risks may be involved with swimming and using the paddleboat. You accept full responsibility for any bodily injury arising from swimming, paddleboat and kayaking and hold owner harmless. You understand there are potential dangers that swimming, paddle boating and water sports may present to children who are not carefully supervised, as well as the danger to any person swimming or using the paddleboat, if a person has health risks, or if a person swims or uses the paddleboat, water sports while intoxicated or using any kind of drugs or medication, or while pregnant. You agree to be fully and solely responsible for any accidents you may incur. You understand the risks discussed above and agree that you will assume all responsibility for yourself and for the consequences of those in your party. You agree to waive any claim whatsoever against owner for accidents or claims arising from swimming, paddle boating or using the kayaks. All Airbnb Guests in my party acknowledge and agree that they have read and understand this waiver and they acknowledge that confirming below constitutes a binding and enforceable contract between Airbnb Guests and Airbnb Host. Guest access Zen Sunset Retreat is rented as complete house, with keyless touchpad and separate entrance. Guest needs to provide 4-digit door PN. Check-In day: Contact/ meet Guest Ambassador, provide ID check, and they will show how how to use keypad, house amenities, and entertainment items. Please coordinate your check in times on AirBnB messaging. BASE price is for 4 Bedrooms, bunk, 2 couches and can sleep 10 people. Optional 5th Bedroom with queen murphy bed, private bath, sunset walkout balcony is available for additional $100/ nite. 5th Bedroom can accommodate 2 additional Guests. Other things to note One third of the lower level is the owners' private quarters, not available/included in the rental. ZSR has separate, independent entry for the owners' quarters. Owners may be on site occasionally during a rental. Base pricing is for 4 Bedrooms and couch to accommodate up to 8-10 Guests. Optional 5th Bedroom with queen murphy bed, private bath and sunset walkout balcony is available addition charge per night. The private driveway accommodates up to 12 vehicles, and street parking is not permitted. Guests with additional vehicles must use the nearby public parking lot; shuttle service may be available for an additional fee with advance notice, subject to availability. For the safety and security of our guests, community, and property, the primary guest is required to present a valid government-issued photo ID upon arrival. As part of our commitment to providing a safe and secure experience, and in response to the increase in AI-generated identity fraud and vacation rental scams, we verify the identity of all primary guests at check-in. Booking Guest Must Be Present: The person making the reservation must be staying at the property for the entire reservation. Third-party bookings or reservations made on behalf of adult children, family members, friends, or other guests are not permitted. The booking guest is responsible for ensuring all guests follow the house rules. Waterfront Pier: One (1) 100' pier with small craft step down directly in front, is reserved for ZSR guests. Other piers and church trails are private property signs. Kindly respect parking and private property signage. To preserve the peaceful atmosphere of Zen Sunset Retreat and respect our neighbors, unauthorized parties, events, DJs, amplified music, and large gatherings are not permitted. Our community is supported by an active Neighborhood Watch, and violations may result in immediate termination of your reservation without refund. Registration Details 001046

Zen Sunset Retreat (ZSR) on the Waterfront

Private Estate, Hot Tub Game Room with 4 Suites

Relax and begin your day with coffee in a rocking chair on the expansive porch and end with a glass of wine on the dock as you watch the stars come out. In between, swim in the pool, paddle out to the Bay or take a nap on the hammock in the shade of the trees. The house has two master bedrooms one on each level with king beds and ensuite bathrooms. Two additional bedrooms are each furnished with queen beds This waterfront poolside retreat has everything for your Chesapeake getaway! The space Voyage to la Maison dans la Lune for a dreamy get away on this one acre property on Parkers Creek in Deale, MD. Outdoor amenities include a large heated pool, hammock and creek-side fire-pit. All set in extensive gardens. Three paddle boards, one sit-in kayak, and one sit-on-top tandem kayak can all be launched from the private dock. The dock is also a great place to admire the view of Parkers Creek, which opens to the Chesapeake Bay just north of Herring Bay Sanctuary or watch for the resident osprey, great blue herring and egret. Living room is outfitted with a sofa and two swivel chairs which can be configured for conversation or theater-seating to watch a movie on the 55" smart TV via your favorite streaming subscription. The large airy kitchen has a five-burner stove, counter-eating for up to six and a small breakfast table that seats four. Step out onto the porch to grill, or eat at the outdoor table which can expand to seat 12. Dinnerware and cutlery for up to 16 means running the dishwasher less often. Two sinks allow food prep to be a group activity without bumping into each other. The round dinning room table can be expanding from six to seating up to twelve. The library is a cozy space to read a book or catch up on your work-from-anywhere. The kitchen, dining room, library and first-floor master all have views of and direct access to, the porch, gardens and water. The living room opens to the pool deck. La Maison sleeps up to 10 comfortably. The large first-floor master bedroom has a king sized bed and it’s own seating area. En suite bathroom has a large walk-in shower plus a soaking tub, and two sinks. Toilet area and shower are equipped with grab bars (though not fully ADA compliant). The second floor has a second master bedroom with a king sized bed, and it’s own en suite bathroom with a large walk-in shower. The two queen-bed rooms, each with their own balcony, have views of the garden and water. They share an adjoining bathroom which has two sinks and a shower/tub. The Game Room can be configured as a hang out space or bedroom via the two, twin fold-outs. This room has its own temperature control separate from the rest of the house. Note: this room must share a bath with another second floor bedroom, which will require walking through that bedroom for access. The house has separate temperature HVAC and hot water heaters for each level, reducing disagreements about the proper temperature for sleeping, or who used up all the hot water. Registration Details 000718

Poolside Waterfront Retreat

Escape to this stunning waterfront home on lovely Carr's Creek in Deale, MD. It offers four bedrooms and full bathrooms, two spacious living areas, two sunrooms, and a large fully stocked kitchen. You can birdwatch from the balcony, snuggle by the fireplace, soak in the hot tub, kayak, canoe, or play games and grill outdoors. Nearby, you can take a charter on the Chesapeake, kayak or hike at the Smithsonian Environmental Research Center, and enjoy local seafood restaurants and antique shopping. The space Seven 5-Star reviews on VRBO- three on other travel sites. Other things to note 100% -- 5 Star reviews on other travel sites. Happy to share upon request. They won't transfer them here. Registration Details 000478

Beautiful Waterfront Escape w/ Gorgeous Views

Welcome to Your IDEALE Getaway! Experience this beautiful Western Shore water view property. Easy access to nearby marinas, scrumptious dining, and a plethora of outdoor activities, this IDEALE retreat is perfect for families, groups, or couples seeking adventure and/or relaxation! Fishing, kayaking, or exploring local cuisine and hidden local treasures there’s something for everyone. A perfect blend of fun, relaxation, or creating memorable moments, book your IDEALE getaway today! Registration Details 000959

Heaven Sent

Come stay with us at Franklin At The Bay in Deale, Md. This 4BR/3BA retreat is 2 blocks from the Chesapeake Bay! Beautifully appointed for style and comfort. Vacation in fun Franklin Manor, featuring private waterfront park, secluded beach, fishing/crabbing piers, small boat/kayak ramp, boat ramp, swimming, playground, basketball, volleyball, baseball. Fast Wi‑Fi and smart TV. 20 min to Herrington Harbor, 30 min to Annapolis, 1 hour to Baltimore/DC. Book USNA Graduation/Commissioning Week! The space This spacious 2-level home features 4 bedrooms and multiple flexible sleeping options: 2 kings, 1 queen, 2 sets of bunkbeds, and 2 rollaway beds. The fully stocked kitchen and open layout make hosting effortless, while over 55 curated amenities—fast Wi-Fi, smart TV, outdoor dining deck, blackout curtains—ensure a seamless stay. Each bedroom is a sanctuary, styled with soft textures, ambient lighting, and calming palettes. The home offers a large footprint, a charming front porch, and a peaceful atmosphere perfect for rest and reconnection. Whether you're sharing a meal on the deck or curling up after a day on the water, every corner is designed for comfort, ease, and togetherness. Guest access Guests have full access to the entire home, including all four bedrooms, living spaces, and the fully stocked kitchen. Enjoy both the front and back yards for relaxing or outdoor play, plus a spacious back deck perfect for outdoor dining and gathering. The property also includes a private driveway with space for up to four vehicles. Everything is yours to enjoy—no shared spaces, no interruptions. Other things to note Just a short walk away, guests can enjoy the Franklin Manor water-privileged community on the Chesapeake Bay, which offers access to secluded beach, multiple piers, a boat/kayak launch, a boat ramp, swimming areas, a playground, volleyball, baseball diamond, and a basketball court (balls provided). It’s the perfect spot for morning strolls, coastal views, and family-friendly fun by the water. Registration Details 000150

Franklin At The Bay

Welcome to the Bachelorette! This bay front home was designed to offer a truly luxurious vacation experience for up to 8 guest. Located on the Chesapeake Bay, it provides breathe taking views from various locations on the property. The home features 3 patio areas, a pier and comfy living spaces for guest to enjoy. The space Our Sunrise suit is sure to provide a one of a kind experience. With floor to ceiling windows and sliding doors you will enjoy spectacular views of the sunrise and the sunset over the bay. Our secondary master suit has its own balcony overseeing this beautiful property. Other things to note We do not allow smoking or animals on property or in home. We do not provide personal items like soaps, shampoos, detergents, toilet paper, paper, paper towels, etc. Registration Details Exempt

The Bachelorette

Chesapeake Paradise Lite 4-5 Br 3 Ba Vacation Home

Welcome to our waterfront oasis on Parish’s Creek just off of the Chesapeake Bay! Our spacious house is the perfect retreat for fishing enthusiasts, nature lovers, and those seeking a serene getaway. With a private pier, kayaks, and easy access to nearby attractions, our home is an ideal destination for your next vacation. Located less than an hour away from Washington, D.C. and 20 minutes from Annapolis, our quiet house provides a convenient escape from the hustle and bustle of city life. The space Across from the Parish Creek Marina, the house is set in a secluded location, ensuring privacy and tranquility during your stay. The panoramic water views from the house and yard are breathtaking, offering a truly immersive experience with nature. The spacious living area is perfect for socializing and spending quality time with loved ones. Turn on the fireplace and relax with a book in the living room, or challenge your friends and family to a game of pool in the game room. Step outside on to the large deck and take in the fresh breeze as you sip your morning coffee or enjoy a barbecue using the grill. Gather around the firepit in the evenings for s'mores and stargazing. With 6 bedrooms and multiple bathrooms, everyone can unwind. The fully equipped kitchen provides top-of-the-line appliances. Brooklinen sheets and William Roam soap offer spa-like luxury. For those who love the water, we provide kayaks for you to explore the serene waterway at your leisure. Considered one of the best places to fish in Shady Side, our private pier on Parish Creek is perfect for fishing or simply enjoying the peacefulness of the water. Imagine sipping your morning coffee or evening cocktail while watching a sunrise or sunset over the bay from the comfort of your own pier. For boat owners, the public boat ramp is only a few minutes away and our pier has a boat slip for you to enjoy the waterway with your own boat. Whether you're looking for a family retreat, a fishing getaway, or simply a peaceful escape, our waterfront house off of the Chesapeake Bay on Parish Creek is the perfect destination. Book your stay now and create unforgettable memories that will last a lifetime. We look forward to hosting you! Guest access The entire property is for guest use, including the long driveway and basketball hoop out front. Please note that front yard abuts the neighbor's backyard without a fence, so we kindly ask that you are mindful of his property. Registration Details 000696

Peaceful Waterfront Getaway

There's nothing like being directly on the water! Relax and rejuvenate in this Chesapeake waterfront estate home which includes private pier, hot tub and fire pit. Crab or fish off the pier or take the kayak out to see the Chesapeake bay wildlife. Try out paddle boarding! Sit around the fire pit at night or watch the stars at night while soaking in the hot tub. Cook wonderful meals in our well-equipped kitchen. Or try some our local restaurants. Great place for families or multi family groups. The space We raised our family here and this property has provided our family and others with wonderful summer memories. Our private waterfront home has 4 bedrooms (three with an attached bathroom) and a total of 4 bathrooms -(plenty for getting ready with multiple guests). This home awaits with 2 balconies, a huge dock , a boat/kayak ramp and 150 feet of direct waterfront on Rockhold Creek which leads to the Chesapeake Bay. This idyllic area of Maryland is just 20 miles south of Annapolis, 15 minutes from Prince George’ s Equestrian Center and about 30-40 miles from Wash DC, Alexandria VA, or Baltimore. Airports BWI and Reagan International are easily accessible. You'll find that the nearby fishing village is like going back in time. This spacious home is 2500 sq ft w/ living rooms on each floor. You will have access to all outdoor decks, pier and yard. Bring a small boat along and launch off our private boat ramp -please discuss with host. When it’s chilly outside you are welcome to use our fire pit to create a comfy cozy place to sing and tell stories and maybe make s’mores. Or, soak and relax in the spa. Sit out on the dock and read a book, sip morning coffee or watch the sunset. The master en suite has a king bed, luxurious jetted tub and separate shower. Adjacent to the master bedroom is a large en suite room with French doors which can accommodate sleeping arrangements for up to 4 people with a queen bed, 2 twins and a daybed and a balcony with an impressive water view. Recent updates added a beautiful new bathroom with shower to the space. The main floor has 2 bedrooms, each with a queen bed. One has a private bathroom and there is a common full bathroom in the hallway. Main floor has a family room with gas log fireplace and a living room with plantation shutters and a water view, for plenty of relaxing. FYI******** In this 3 level home, the lower level is hosts’ space and not included. They have a private walk out entry and the other main floors are locked off from one another. Currently hosts Natalie (and husband Allan) stay during the week and stay elsewhere on weekends. They have a lovable golden doodle, Lilly. When hosts are there, their apartment is completely separate and no living space is shared. They have a separate waterside entrance. Hosts are available when needed. This is a traditional Airbnb where hosts reside on the property some of the time. We respect our guests privacy and we stay out of your way. This has been a transitional year with job changes and Allan and Natalie sometimes stay in the apartment during the week, however we stay elsewhere during the weekend. We value our guests and we have been Airbnb hosts for 11 years. If you have any questions please send an inquiry.I Guest access Home is for registered guests only. No unauthorized parties, gatherings of other people at the house or a fee of $1000 will be charged. Guest must agree to house rules regarding this. Please check with host for more information. You will have access to our entire house except the basement level. We have a well-equipped kitchen for your cooking needs and all kitchen appliances including toaster, coffee maker and Keurig and spices. We have: Free Parking for several vehicles Pier use for fishing and crabbing Concrete boat ramp for launching small boats Pier to tie up smaller boats, up to 20 feet Deck with seating Kayaks Stand up paddle boards Other things to note I have several kayaks that I offer to guests to use during their stay. Guests love to take a scenic kayak ride and see birds and enjoy getting away from the city. Host provides flotation devices in many adult sizes and a few smaller child sized ones. If you have a small boat that you want to dock, we can make arrangements for you. You must bring your own tie ropes to secure it. If the tide is high enough you may use our boat ramp to launch. Registration Details 000018

Chesapeake Waterfront-3 En Suites-Fire Pit-Kayaks

Quiet town We call it "Fredelig Sted" peaceful place with a Norwegian touch The space Beautiful location right on the Bay shore where you can see the swans in winter and the sailboats in summer. Guest access The entire house is yours to enjoy--2 bedrooms first floor and 2 bedrooms second floor Registration Details 141824

Million Dollar View

Work and play in the luxurious comfort of this beautiful five-bedroom water-view family home with large yard, front porch, and back deck. Stroll down to Carr's Wharf pier at the end of the road. Drive 5 mins to Beverly Triton Nature Park and Beach on the Chesapeake Bay, 14 mins to Smithsonian Environmental Research Center and 20 mins to picturesque Annapolis. The diverse attractions of Baltimore and DC are close by. Perfect for family, vacation, and working from home. The space BBQ or simply relax on the large deck adjacent to the family room. Marvel at the gorgeous sunrises over the water from the master bed, master bathroom, or the second-floor deck. Soak up nature on the lovely local walks. Launch your boat from one of the many marinas close by and take in the incomparable beauty of the largest estuary in the United States, the Chesapeake Bay, home to more than 3,600 species of plants and animals. Guest access Stress-free check-in with the smart lock. Enjoy the entire home including the kitchen, dining area, family room, living room, hallways, all five bedrooms, front porch, back deck with BBQ and a half-acre of grounds. Secure, safe, off-road parking is available for five cars. Other things to note The base price accommodates 2 people. Additional guests are extra. Registration Details 000021

Sundrenched waterview primo family holiday retreat

Chesapeake Escape is a completely rehabbed home within walking distance of Herrington Harbor, Ketch 22, and the Chesapeake Grill/Deli. Not far to Annapolis,DC,&Calvert County; which has a boardwalk,public beaches,water park,boat rentals(crab/fish) & casino! Our 4 bedroom, 2 bath home accommodates up to 14 people with a completely stocked kitchen. There are 4 tv's inside the home plus games for children, as well as adults. Nice size back yard has a tiki bar with a tv and dining area. STR00986 The space Bedroom 1: Queen Bed Bedroom 2: Queen Bed Bedroom 3: Triple bunk bed (1 full and 2 twins) Bedroom 4: This is a small nook seperated by a curtain within the 3rd bedroom. It has the same entryway as the 3rd bedroom. 1 full bed and small couch that lays lat. Theme Room: 1 full pull out couch Living Room: Queen pull out couch COTTAGE LIVING: Smart TVs w/ Roku, dining table,Furnished patio, Tiki bar with tv, furnished front porch KITCHEN: Stainless steel appliances, stove/oven, microwave, dishwasher, refrigerator, dishware/flatware, Coffee machine, toaster, knife block GENERAL: Free WiFi, washer/dryer, linens/towels, central air conditioning, hair dryer FAQ: Stairs required, No pets allowed PARKING: Driveway (4 vehicles), free street parking Guest access Other things to note - No smoking - No events, parties, or large gatherings - Must be at least 25 years old to book - Additional fees and taxes may apply - Paper towels, toilet paper, and garbage bags are provided as a starter supply. For longer stays guests must buy their own once they run out. - NOTE: The property requires stairs to access Other things to note Guests who stay at this property will sign a short term rental argreement agreeing to the rules and check out procedures. Early Check-In Need to arrive early? We may be able to accommodate early check-in for a $75 fee, depending on whether the home is ready. Just message us ahead of time and we’ll do our best! Registration Details 000986

Chesapeake Escape

Luxury Home, Sleeps 15, Private Pool, Close to DC

Enjoy this unique and tranquil getaway only minutes away from the Western Shore of the Chesapeake Bay and less than hour from Washington, DC. A gorgeous, custom home with relaxation and connection to the outdoors in mind. Surrounded by twenty acres of beautiful forest with a flourishing bird sanctuary. The property is surrounded by Tracey's Creek Watershed in Deale, MD and only 25 minutes from Annapolis. The space Enter the private foyer with half bath and staircase that lead to the spacious 1700 sq ft apartment upstairs. 4 bedrooms, 2 bathrooms and a short ceiling loft with 2 extra beds. The full kitchen, dining, and living space are gorgeous and the perfect place to gather and retreat with family and friends. The large outdoor deck (12' x 30') is partially covered. The loft is only accessible by an affixed custom ladder with the 2 additional twin XL beds under short ceilings. The two full bathrooms are considered 3/4 bathrooms because there are no bathtubs, only beautifully tiled showers, one with a high window to the view the outdoors. With advance notice, one of the bedrooms with two twin XL's can be converted to a king size bed. Depending on timing and advance request, a third 3/4 bathroom may be made available on the first floor. While your entire space is private, owners may be on the property in an attached private space and will always respect your privacy. Guest access Guests have complete and private access to entrance foyer with a half bath. A large set of stairs leads to the 4 bedrooms, spacious living room, dining area, full kitchen, loft (only accessible by an affixed ladder), 2 3/4 bathrooms, large partially covered deck, and washer/dryer. Confirmed guests receive an entry code the day of arrival. Short walking trails are accessible. Maps are at entrance and in welcome book. The property has been determined as a Forest Dwelling Bird Sanctuary by the Maryland Department of Natural resources. It is a bird-lovers paradise. Other things to note Please note that the entire space, less the foyer and half bath, are up a flight of stairs and all completely private. Please see pictures as this will not work for anyone who has a problem getting up and down stairs. The owners may be on site in the downstairs private area and may stay the night. We often access the garage and private section of the house on the first floor or walking the property (with or without their dogs). With advance notice, two of the twin XL's can be converted to a comfy king. Depending on timing, a 3rd 3/4 bathroom may be made available for private use and included in renters private space if requested in advance. Please note that while we allow events, you must have prior approval from us first, pay a security deposit of $250 (returned after inspection of house with no damages) and no one other than registered number of renters permitted on property during the house quiet times of 10:00pm to 7:00am. Events are limited to 25 people. Registration Details 000667

Harmony Hills Hideaway

Enjoy the Chesapeake Bay in this brilliant 3-bedroom, 3-bathroom mid-century modern home nestled in the heart of Deale, MD. An expansive take on a European chalet, this unique home features a large salt-water pool and an oversized patio with plenty of seating to enjoy the water view. Built by the owner of DC’s iconic Brickskeller bar as his personal retreat, this haven’s distinctive modernist architecture with massive exposed beams throughout could simply not be reproduced today. The space 2024 Update: New Poolside Hot tub installed! An open concept and a well-appointed chef’s kitchen with a sizable island make this home the perfect space to relax and entertain comfortably. The home’s four living room areas are tastefully furnished and include a main space with soaring ceilings and water views, and a cozy area with an enchanting starlight ceiling. The beautiful glass sunroom overlooks the patio and pool areas and has views of Rockhold Creek. The master suite has a balcony facing the creek where you can enjoy the sunset. There is a second bedroom and two loft areas on the second floor, and a third bedroom on the main floor with a view overlooking the pool and creek, and overall plenty of space for your family to unwind and enjoy each other's company. *The pool can be heated by request. The cost is $100/day. During April/May & October/November we can't guarantee a set temperature. Guest access Sleeping Arrangements: Main Bedroom Upstairs - (1) King Bed and (1) Smaller Sofa Bed (for children) Bedroom #2 Upstairs - (1) Queen Bed and (1) Bunk Bed (2 singles) Bedroom #3 Lower Level - (1) Queen Bed Loft Area #1 Upstairs - (1) Sofa Bed Loft Area #2 Upstairs - (1) Sofa Bed Other things to note Pet fee is $100 per stay. Registration Details 000668

Modern Bay Dream

Large 4-story Chesapeake Bay retreat just a short 4 minute walk to the North Beach boardwalk, beach, pier, and restaurants. Enjoy bay views, multiple decks, a game room, and plenty of room for families and groups to gather. Perfect for beach trips, weekend getaways, and special celebrations to include weddings at Herrington Harbor North or South. The space Main Level – Entertain & Relax Step into an open-concept living space designed for connection. The spacious layout is perfect for entertaining. Slide open the doors to the extended deck, where you can dine al fresco, enjoy your morning sunrise coffee, or cool breeze evening cocktails. Second Level – Rest & Refresh Upstairs, you’ll find three large bedrooms, 2 of which have boasting stunning Bay views. The convenient laundry room is right on this level too—because even on vacation, ease matters. Top Floor – Your Private Retreat The entire upper level is yours: an oversized primary suite with a spa-like bathroom, walk-in closet, and private deck overlooking the Chesapeake Bay. It’s the kind of hideaway that feels like an upscale boutique hotel—without ever leaving home. Garage & Backyard – Extra Space, Extra Fun The supersized garage fits up to two cars, has a game room and opens directly into the fenced backyard through sliding glass doors—great for both gatherings and quiet afternoons. Whether you’re planning a family beach trip, a couple’s retreat, or a group getaway, this North Beach gem offers the perfect blend of comfort, luxury, and unbeatable location. Guest access The entire house is yours to use and enjoy. Other things to note Please include all guests in the reservation count so we can insure the place is set up just right!

Bayview, Walk to Beach & Boardwalk Perfect Getaway

Expansive views of the Chesapeake Bay await from this private and peaceful West River retreat. Immaculately maintained, this home offers a large open floor plan, a private dock with boat lift, and a one-car garage. The setting is quiet and secluded, with beautiful waterfront views and plenty of space to relax, entertain, and enjoy life on the water The space Enjoy the best of Maryland waterfront living at this peaceful West River getaway. Located just off the Chesapeake Bay, this private waterfront home offers beautiful views, a spacious open layout, and everything you need for a relaxing stay on the water. The property features a large private pier with approximately 6 feet of mean water depth, making it a great spot for fishing, crabbing, launching kayaks, or simply enjoying the breeze by the river. Guests can spend the day exploring the water, relaxing in the yard, or gathering outside for a classic Maryland crab feast. Inside, the home offers a comfortable open floor plan with plenty of space for family and friends to spread out. The property also includes a one-car garage for added convenience. Outdoor amenities include kayaks, bikes, cornhole, yard games, board games, a propane grill, and an outdoor seating area perfect for picking crabs, grilling dinner, or enjoying evening drinks by the water. Whether you are planning a quiet weekend escape, a family vacation, or a Chesapeake Bay adventure, this West River home offers the perfect mix of privacy, comfort, and waterfront fun Guest access The entire property is for Guest use. Registration Details 000707

West River Waterfront w/ Pier, Kayaks & Bay Views

This lovely contemporary home has five bedrooms and 3 baths. The 1st bedroom also has the homes washer and dryer. Large dining room with a table that seats 12. An even larger living room with 3 roomy couches for lounging, chatting and enjoying the view. The living room features a Steinway Grand Piano. There is a beach, deck and screened in porch. Their are empty drawers in each bedroom as well as room in the closets for weekend hanging cloths. The house is the owners primary residence. The space Just minutes from downtown Annapolis but the house is set at the end of a peninsula in a wooded quiet setting. The minimum stay is 3 nights for $2400. Bedroom #1 has one double bed plus laundry access, Bedroom #2 has a queen. #3 has a queen, #4 has two doubles, #5 has one king. There are two full baths on the second floor and one full bath on the first floor. Guest access Guest have access to the home, washer,dryer etc and a small beach. There is room for 4 cars on the property. There is no on street parking available in the community for additional cars. Other things to note The home will be professionally cleaned before your arrival. This is owners primary residence. Bedroom closets have adequate hanging room for a long weekend stay. Refrigerator (26.0 cubic ft.) All open shelves are empty for your use. I/2 the freezer is reserved for your use. There is a large community beach 2 blocks away. There is a small private beach on the property. Registration Details 000179

Beautiful Waterfront Home Sleeps 12

Spread out in this 4-bedroom retreat with a fenced-in pool, large backyard play area, and spacious eat-in kitchen - built for families who want room to roam. Located in quiet South County, you're 20 minutes from Annapolis and 45 from D.C., with 7 beds and 3 full baths so everyone has their own space. Fire up the grill, swim all afternoon, and gather around the kitchen island for dinner. The space The main floor centers on a large eat-in kitchen with modern appliances, plenty of counter space, and seating for the whole group - this is where everyone ends up. The living area connects directly, so the cook never misses the conversation. Bedroom 1 has a king bed, Bedroom 2 a queen, Bedroom 3 two doubles (great for kids), and Bedroom 4 a queen plus two singles. Each of the 3 full bathrooms is stocked with fresh towels. Bedroom Location: Bedroom 1 is conveniently located on the main floor, while all other bedrooms are located upstairs. Out back, the fenced-in pool is the star—surrounded by a large yard with a play area for kids. The driveway offers ample parking for multiple vehicles, including space suitable for larger vehicles or RVs (no hookups available). Guest access Guests will have access to the home by keypad entry. Other things to note -Parties or events are strictly prohibited. -Only pets below 50lbs allowed at $100 per pet, maximum 2. -All cars should all remain in the driveway. -Early check-in and late check-out are available upon request and subject to availability. One hour may be offered complimentary when possible. Additional time is available for a fee: • Early check-in before 3:00 PM – $50 (must be arranged in advance) • Late check-out after 12:00 PM – $50 (must be arranged in advance) Please request in advance so we can confirm availability. -Pool access will be unavailable starting at the end of September. -Small charcoal and propane grill BBQ available for guests' use. -Smoking is strictly prohibited on the property; if any evidence of smoking is found that requires additional cleaning or remediation, the associated costs will be charged to the responsible party. Registration Details 002125

Pool & Yard Retreat | 4BR | 20 Min to Annapolis

Waterfront Enjoyment: A 3-bedroom, 2-bathroom home! This charming one-story house in Churchton, Maryland, is perfect for families. It includes 8 acres of land and over 700 feet of waterfront on Broadwater Creek, ideal for fishing, crabbing, paddleboarding, and kayaking. Discover the charming town of Deale, Maryland, with its easy entry to the Chesapeake Bay. Relax and enjoy this property! There's a brand-new 140-foot dock with beautiful views of the bay, ideal for catching crabs and fish! The space The property includes 8 acres, a swing, and a fire pit. You can launch kayaks (3) and paddleboards (2) into the water. Fishing is allowed, and two mountain bikes are available. Swimming off the dock isn't permitted. However, a brief paddleboard or kayak trip (5-10 minutes) will take you to a sandbar suitable for swimming. A recently built, lengthy dock (140 feet) is there for fishing and crabbing. Guest access Entire Large Home on the property. All other buildings, except the Activities Shed, are off-limits. Registration Details 000104

8 Acre Waterfront Oasis! Pets are Free! 140ft Pier

Waterfront Cottage@ChesapeakeParadise Hot Tub/Dogs

Breathtaking sunrises and panoramic Chesapeake views steps from the Bay. Situated in a quiet neighborhood within an hour of DC, 30 minutes from Annapolis. Enjoy bay breezes, boats on the horizon, and local wildlife from our covered porch. Take a dip in the Bay or explore in our kayaks. Inside, enjoy thoughtful updates and perches placed for enjoyment of the Bay. The space Our home's common space has 180 degree views of the Chesapeake Bay. The second floor is the master bedroom suite with a queen bed and 2 twin beds, private bath with a double sink vanity, and work area with desk. The first floor offers two smaller bedrooms, one with a queen bed and private bathroom with tub/shower, the other with two twins, a desk, and adjoining bathroom. The kitchen is well appointed with cooking spices, pots and pans, paper towels and napkins, condiments and a Keurig coffee maker. Our outside area offers a relaxing porch and patio. There is parking for as many as 4 cars. There are 4 kayaks (one child-sized) available with paddles and life jackets. The community features a ten foot wide easement for strolling along the Bay as well as a community pier. Guest access The entire house (except for a small owner's closet) and yard are available to our guests. Kayaks are in the garage, but the garage is not available for parking cars. Other things to note Smoking is not permitted on the property. No pets are permitted. For safety reasons, use of the fireplace is not permitted. The closest grocery store (Christopher's) is approximately 5 minutes away. Registration Details 000146

"Seas the Bay Cottage" in Deale with Kayaks

Enjoy a relaxing coastal getaway just minutes from North Beach, MD and the Chesapeake Bay. Perfect for summer days filled with beach walks, waterfront views, local dining, fishing, and outdoor activities. Unwind in a cozy space after a sunny day by the water and enjoy the peaceful charm of the area. Whether you're here for a weekend escape, family trip, or summer break, this stay offers comfort, convenience, and a true coastal experience. The space Our Home Features: •⁠ ⁠4bedrooms and 4.5 bathrooms •⁠ ⁠⁠Primary suite upstairs with walk-in shower and soaking tub •⁠ ⁠⁠Second primary suite on the main level, ideal for guests or multi-generational living •⁠ ⁠⁠Bonus room on upper level for office, playroom, or lounge •⁠ ⁠⁠Rear deck, perfect for relaxing, entertaining, or enjoying the outdoors •⁠ ⁠Private two-car driveway •⁠ ⁠⁠Walkable to the boardwalk, beach, shops, restaurants, and breweries (10 mins) Designed for everyday comfort and convenience! North Beach Summer Events & Local Guide 🎬 Movies on the Beach Enjoy free outdoor movie nights right on the sand in North Beach throughout the summer season — perfect for families, couples, and weekend beach travelers. Bring your blankets and chairs for a relaxing movie night by the Chesapeake Bay. 2026 Movie Schedule: - September 19, 2026 — Jurassic World: Rebirth 🎉 First Fridays on the Boardwalk 6:00 PM – 9:00 PM | Bay Avenue, between 3rd and 7th Street North Beach's biggest monthly community event — DJ music, classic cars, food trucks, beer and wine vendors, local artisans, and free beach access. A lively bayside night out, rain or shine. Upcoming dates: August 7 & September 4, 2026 Note: parental supervision required for anyone under 18. 🥕 North Beach Farmers' Market Every Saturday | 8:00 AM – 11:30 AM Held at 9010 Chesapeake Ave from April through October, the North Beach Farmers' Market features fresh local produce, baked goods, seafood, crafts, and small-town coastal charm — perfect for a weekend stroll by the bay. Local Favorites & Beaches — North Beach Living Situated just moments from your front door, North Beach delivers relaxed coastal charm and vibrant community energy. Spend sun-soaked days at the sandy Chesapeake Bay beach and scenic boardwalk, perfect for swimming, sunset strolls, and catching the refreshing bay breeze. The inviting waterfront also features a fishing pier, boat slips, and flower-lined paths that make every walk a pleasure. When it’s time to dine or explore, local favorites are within easy reach: • Enjoy fresh seafood and coastal fare at Hook & Vine - Kitchen and Bar or Neptune's Seafood Pub. • Sip local wine and artisanal cheeses at the acclaimed Vaughan Cheese Counter & Bar or unwind at The Wheel House Beer Garden. • For casual meals with local flavor, try tacos at Plaza Mexico or classic bites at Ketch 22 and Chesapeake Market & Deli. • Start your day with coffee and treats from the bakist, or grab local produce and goods at the seasonal farmers market. With boutique shops, seasonal events like First Fridays, and the welcoming waterfront just steps away, North Beach is an inviting destination for everyday living and leisure alike. We provide 2 complimentary beach passes with your stay! Each beach pass allows entry for up to 5 guests, making your beach days even easier and more convenient. Please note: beach passes must be returned upon check-out. Lost or missing passes will incur a $100 replacement fee. Other things to note This property has special local compliance requirements which include a signed rental agreement, ID verification, and a security hold of $1000 (which is not a traditional security deposit, just a pending transaction). As an optional alternative to the security hold, you may opt in to purchase a non-refundable damage waiver provided by a third-party insurance company. The optional damage waiver is $37 for stays up to 10 nights, with an additional $2 per day for stays longer than 10 nights. Damage waiver purchases are optional. To make this process easy for you, we use a secure and very simple, app-free platform called Happy Guest. It is not an app, and you do not have to sign up for an account - it’s a safe and secure website. It also gives you a guest portal with all the info about the home and all of my favorite local spots. If you have any questions, just message us anytime! Happy to help!

Modern Bay Home a few blocks from Boardwalk

Your next maritime retreat awaits at this 5-bedroom, 2-bath Edgewater vacation rental! Featuring 2 Smart TVs, a fully equipped kitchen, and a spacious yard, ‘Turkey Point’ offers at-home comforts and on-site entertainment galore. Sip your coffee from the deck before heading to Holiday Hill Marina for a day on the water. Hoping to get your toes in the sand? Mayo Beach Park is less than 3 miles away! Wind down at home with a dip in the hot tub or roast s'mores over the fire pit with the kids. The space Anne Arundel County STR Registration: STR-00499 | 2,350 Sq Ft | Self Check-In | Walk to Selby Bay  Bedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Full Bed | Bedroom 4: Twin Bed, Twin Sleeper Ottoman | Bedroom 5: Twin Bed  INDOOR LIVING: 2 Smart TVs, dining table, breakfast bar, wet bar w/ wine cooler, private hot tub, books, board games, ceiling fans OUTDOOR LIVING: Furnished deck, gas grill, fire pit, cornhole, private yard KITCHEN: Dishware/flatware, cooking basics, spices, Keurig coffee maker, Crockpot, microwave, water filter, ice maker GENERAL: Free WiFi, keyless entry, central A/C & heating, linens/towels, iron/board, trash bags, paper towels, hair dryer, complimentary toiletries FAQ: Access only by stairs, 1st-floor bedrooms, 2 Ring doorbell cameras (facing out) PARKING: Driveway (3 vehicles), trailer parking available Guest access Guests will have access to the entire property via keyless entry Other things to note - No smoking - No pets allowed - No events, parties, or large gatherings. Do not exceed the maximum occupancy at any point. This rule is strictly enforced - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This property requires stairs to access and while there are 4 bedrooms on the 1st floor, the remaining bedroom is located on the 2nd floor and requires additional stairs to access - NOTE: Your safety matters. This property features 2 Ring doorbell cameras: 1 camera is located next to the front door facing out towards the front entry area and 1 camera is located next to the back door facing out towards the deck and backyard. These cameras do not look into any interior spaces. These cameras record sound and video when activated by motion and will be on during your stay Registration Details 000499

Coastal Edgewater Home w/ Private Hot Tub!

Shady Side is a quaint town located 35 min. from Annapolis and an hour from Washington, D.C or Baltimore. This waterfront home is perfect for families or small groups looking for a relaxing getaway on the Chesapeake Bay. Enjoy the wrap-around screened porch, private pier with ladder for swimming, large yard, and an incredible view of the Bay Bridge. Free public boat ramp 5 minutes away in Parish Creek. Listed for 8 people max. Contact us for approval of 1-2 more. The space Shady Side is located at the mouth of the West River near Parish Creek. The bay is located just beyond Curtis Point. There are views of the Bay Bridge on a clear day! We enjoy swimming off the pier. Normal, average water depth ranges from 2-4 feet, depending on the tide. Annapolis is 35 min away. The kitchen is fully equipped for cooking. A 2 seat kayak with paddles and life jackets are available for use. Other things to note Water safety is paramount. No running on the pier or diving. It is a residential neighborhood. Be respectful of neighbors and maintain quiet after 10pm. Registration Details 000233

Waterfront w/ Private Pier, 35 Mins to Annapolis

Welcome to A Haven Away! Our home has 4 bedrooms (2 king beds + 2 queen beds). 2 mins to the beach, restaurants, and wetlands. We have a private, landscaped backyard perfect for dining and lounging. We provide beach passes, beach gear, games, a Pack & Play, and tips for jet ski rentals and day trips. The shed has a huge Smart TV. Fully-equipped kitchen. Single-story living with 2 bedrooms, accessible shower on the ground floor. The space Gorgeous, recently renovated 4 bedroom house with four large bedrooms (two on the ground floor and two upstairs) and 3 full bathrooms (one has a bench and grab bar). Use the house as your base for local activities- including fishing, sailing, kayaking, paddle-boarding, biking and more. North Beach has everything and this is the perfect spot to enjoy it all! Host dinners outside at home using our fully equipped kitchen and our large patio table under the stars, or choose from our list of recommended restaurants or local activities. Relax afterwards on the front porch or back-deck (with smokeless firepit); chill out on the beanbags in our secret library that kids love; or even burn it all off with yoga or on the bike in our exercise room! The house can sleep 8 adults (two king beds and two queens). With 3 full bathrooms there is plenty of room for everyone. North Beach is close to big cities like Washington, DC and Baltimore- but feels a million miles away. You'll head home refreshed, relaxed and happy! Looking to visit Washington, DC, Harpers Ferry, or the second longest beach in Virginia? We have several comfortable and stylish homes in the area. Check out our profile or message us for details! Guest access The house, fenced-in front and back yards, and TV/exercise shed are all yours. You can park 3 cars directly in front of our white fence. There is space for additional cars around the corner of our house. Other things to note We allow reliably house-trained dogs for a $25 pet fee per dog per night for stays under 7 night. If you want to bring your dog, please let us know: - If they are 100% reliably house-trained - The dog's age We must approve their stay, but we have never rejected a reliably house-trained dog. We do not allow cats or puppies. We would really appreciate it if you could bathe your dog before visiting. ** If you're not a pet person, note that we are very good at keeping our homes super clean despite hosting pets. ** No smoking. No incense. No parties. **

Huge 4 BR Beach House | Fire Pit | Fenced Yard

Perched on a bank overlooking expansive views of the Chesapeake Bay, our shingled cottage is a comfortable country retreat with exposed beams and cathedral ceilings. It is less than an hour to Annapolis and Washington DC. Save on your first Airbnb stay (some restrictions apply): https://abnb.me/e/i9PHYamHUN The space A true retreat, our cottage offers you a cozy place to enjoy the quiet, laid-back country lifestyle, with a serene, panoramic view of the Chesapeake Bay and the mouth of Deale Harbor from our deck or enclosed porch. You may relax on a bench in the shaded gardens, or do some outdoor grilling on the double broiler in our picnic area. Master BR has a King bed for 2, which is adjoined to Bedroom 3, which has a has a twin day bed (or may serve as an adjunct room to create a Master suite); BR 2 has a Queen bed for 2 (with an additional window seat that can serve as a toddler bed); and 3 twin beds under skylights in an open loft reached by library ladder! Guests should consider the convenience of one bathroom. Our family cottage was built in the 1920s, redesigned in the 1990s and updated more recently, retaining at its heart the original rafters and open ceiling, brick hearth and chimney built by our grandfather. It is appointed with all modern amenities, comfortable furniture and interesting decor. Families from Washington, DC flocked to the Chesapeake Bay to escape the heat of the city, enjoy summers by the water and outdoors. Today, we enjoy all four seasons at the cottage; we hope you will, too. Guest access Outside, you will have access to a wide deck with teak furniture and umbrella; a screened porch with seating in wicker chairs, and an Italian tile dining table with seating for 8; a double broiler gas grill, picnic table and outdoor seating in one area; park bench in shaded areas. Indoors, you have access to a fully-equipped kitchen; comfortably furnished home; many board games, and all linens and towels. The washer/dryer are in a separate utility room. Other things to note We expect guests to follow the posted checklist on departure, and to leave the cottage as they found it. The closest grocery is about 20 minutes away, so it may be most convenient to bring your groceries with you before arrival. We stock some staples for your use: oil and vinegar; salt and pepper. We are sorry, but for safety reasons, we are unable to allow guests to use the fireplace. Registration Details 000130

Charming Waterfront on Chesapeake Bay

Forget your worries in this spacious and serene getaway. Located less than an hour from DC/Baltimore, you’ll find this comfy getaway tucked across from the Chesapeake Bay and right around the corner from restaurants & bars, shops, boardwalk, and marinas. This private home boasts cozy furnishings, indoors and out, with plenty of space to relax with family and friends. With 4 bedrooms, 2.5 bathrooms, large open kitchen and living room, front and back outdoor lounge with fenced in yard and firepit. Registration Details 000731

Getaway by the Bay

The whole group will enjoy easy access to everything from this centrally located place. The space large bay front home w 3 decks

Bayviews

Waterside mid-century modern home, perfectly appointed. Join with colleagues, family, and friends. Paddleboard, roast marshmallows, watch fireworks, take a hot tub or team building. Our "Flight Deck" is perfect for meetings and retreats. Breathtaking, peaceful grounds with an abundance of space. Approximately 2800 SF sits on a 3/4 acre property - perfect for lawn games and zip lining. 20x20 furnished deck + dock Mayo Beach and Beverly Triton 1 mile away. Within an hour of the DMV The space -This exceptional space has three common/family rooms, five bedrooms, a large open concept living/kitchen/dining room space with 180-degree views of the water, which also includes a deck off the living room. The house has four bathrooms and six parking spaces in the driveway with available street parking as well. -The house comfortably fits 8 adults and up to 4 children. -There is a family room/game table with a sectional and play area with tons of toys for kids and puzzles/games. -The studio has a game/workspace with a large television and a sleeper sofa. -Collaborate with ease using our large format smart TV’s Chromecast/airplay technology. Sonos is also set up. -The fully equipped kitchen makes organizing meals a snap. -Overnight retreat/vacation options are available as well as day-long meetings reservations. This exceptional space is less than an hour from DC, Tysons, and Baltimore. We look forward to hosting you in one of the region’s best-kept secrets. -Outdoors you will have an idyllic view of the Big Pond and will witness the gorgeous birds taking flight in this bird sanctuary. There is plenty of space for relaxing on one of the many decks all with water views. Kids will have a blast with all the lawn games and there is even a light-up zip line! - Hot tub - Firepit -Walking distance is Mayo beach and our favorite beach/nature park for trail walking and swimming (Beverly Triton) is a 3-minute drive. Guest access You have full access to the property with the exception of owner closets - which are locked. There are a few kitchen shelves set aside for owner items but otherwise enjoy the home. We will email directions on using the space the night before your check in. This will include codes/access/eateries/beach information and all details on enjoying the house! Other things to note The house is set up nicely for family gatherings or even a couples weekend. There are great spaces for cooking and entertaining. The outdoor decks can seat up to 18 for dinner over two tables. There is flex seating as well. We also have a folding table. There are toys for toddlers and lawn games including croquet, frisbees, can jam, simple baby pool and more fun stuff. Board games and lots of puzzles will keep the whole family happy. The furnishings in the house are just months old and the entire house has been newly renovated. Registration Details 000121

Luxury Modern Home on Water+Hotub- Annapolis 25min

Cottage Located directly on the Chesapeake Bay. Includes sandy beach, yard, a screened in porch and deck. Two Kayaks to enjoy. Two bedroom plus den. Two full baths. Fully equipped kitchen.Kurig coffee maker and regular available. Master bedroom -queen size mattress. Second bedroom -a full-size mattress (double) third bedroom -a twin day bed with twin pullout. Both twin size mattresses. Registration Details 142284

Chesapeake Bay Cottage

Cottage style with water view of Rockhold Creek. Water taxi right out front of house to take you to local restaurants. Crabbing excursions or fishing charters available for extra cost. Dog friendly. Local restaurants all within 1 mile from location. Fenced in back yard. Picnic table and fire pit to have own personal crab feasts or cookout. Many local restaurants with outside musicians.Grocery store and gas/liquor stores within 5 minutes from house. The space Very cozy and comfortable pet friendly home. Beautiful views of Rockhold Creek and boats and waterfowl. Private fenced in backyard with fire pit perfect for relaxing with your furry family members! Registration Details 000217

Hannah’s Hideaway

Escape to Serenity: Chesapeake Bay Oasis. Experience the ultimate Chesapeake Bay retreat - stunning 6-bedroom, 3-bath water-view villa, perfectly suited for family reunions & special gatherings. Enjoy breathtaking bay views, steps from the water's edge, with gated 240’ pier, sandy beach, protected swim area, picnic tables, BBQ grills & children's playground. **6-person Outdoor hot tub** The space 6BR/3BA two-level Chesapeake Bay waterview home. Sleeps 16+. Parking for 6 cars. Penthouse-level: 1 Cal King with ensuite bathroom (2-person jetted spa tub), 1 King, 1 Queen, 2nd bathroom with tub/shower and decolav sink. Gourmet kitchen with bar. Relaxing living and dining areas (open plan with decorative arches). Dining table (seats 8 total) and bar (seats 2). Garden level: 2 Queen, 1 full bathroom with double vanity sinks, 2 sets of bunk beds (sleep 4) plus Queen sleeper sofa (sleeps 2). Landscaped garden, patio heater & BBQ Grill, outdoor SPA TUB, nature lovers garden with wildflowers and perennials. Best place for family reunions and weddings. Guest access Entire main house. Exclusive use of whole house, front & side yard toward the Chesapeake Bay. Back yard (except for pathway only access to back door of main house) is not part of this rental; reserved for guests in detached Studio. Non-smoking house. Smokers and cigar aficionados are welcome to enjoy outdoors provided you throw away butts. Many thanks! Other things to note Similar to a 4-star hotel, we provide fresh linens, bath towels, soap & shampoo, hair dryers, iron. In addition, you'll enjoy 2 fully equipped kitchens, books, music cd's and dvd's, 2 kayaks/vests/paddles, Jacuzzi spa tub, bocce ball and more. Better than most upscale hotels in the area, you have exclusive outdoor and indoor space to enjoy - and of course a waterfront community with gorgeous Chesapeake Bay views, gated pier, sandy beach, playground and boat ramp (opt). For your exclusive use: 2 kayaks, vests, paddles and dollies. We love to host family reunions. Best hotel Annapolis alternative. Guests are responsible for municipal pool fees. $75/night boat slip fee (2 night maximum stay). Luxurious Amenities: Spa-Inspired Retreat: Indoor and outdoor spa tubs, perfect for relaxation. Outdoor Delights: Hot tub, gas BBQ grill, firepit, and a beautifully landscaped garden with wildflowers & topiary. Gourmet Kitchen: Equipped with a bar, ideal for culinary enthusiasts. Exclusive Use: Entire main house, front & side yard, with private parking for 6 cars. Additional Perks: Fresh linens, towels, soap, shampoo, and hair dryers provided. 2 full kitchens, books, music CDs, DVDs, and more. Kayaks, vests, paddles, dollies for exploring the bay Registration Details 000190

Crow's Nest Cottage: Chesapeake Bay View*HOT TUB*

Four Bedroom Retreat with Bay Views!

Bring the whole family to this spacious home on the waterfront with its private pier. With high ceilings and large windows, this home gets beautiful natural lighting. The neighborhood is peaceful, quiet, and 10 minutes away from Annapolis. No carpet ,all wood floor. The space You are fully equipped with basic home essentials to make you feel at home. There are three new foam king beds and three new foam queens. The living room is large and significant for a family get-together with an 82" Smart TV, one 75" TV in the main bedroom, and one TV on the level for playing games,2 TV in bedroom, total 5 TV in house. There's also a dedicated workspace if you want to work from home. House has six bedrooms and 5.5 baths. Second floor, four bedrooms, and three full bathrooms two suite bath , other jack and Jill. First floor. suite bathroom , and one haft bathroom. The lowest level (basement) has one bedroom and a bathroom, a Game room with 100 in TV, a ping pong table,five kayaks Three kayaks single seat free play Two kayaks, double seats. Parking is available for six cars. Upgrade all floor lowest level Other things to note One room in the basement used for stock Registration Details 143769

Waterfront Cheerful 6 BR Home with Private Pier

Our home is located in a quiet residential waterfront community. You'll love our place for its cleanliness, privacy, and proximity to the water. From the front yard, you have a distant view of the Chesapeake Bay. Half a block away, you'll have access to the community piers, playground, volleyball court, baseball field, and kayak loading dock. We have three kayaks, which you can use. A private and sandy beach is located a short natural trail walk away. You'll love the wildlife of the bay. The space Our home is about 1600 sf and has a fenced backyard, front double porch, and rear screened porch. Our home also located in front a community green space, providing a nice sight line of the bay. The main level of the house has an inviting living room, an open kitchen-dining room area, dedicated office desk, and a powder room. Upstairs has three bedrooms and two full bathrooms. Owner's suite has a king bed, tv, and its own private balcony. The second bedroom has a queen bed and a desk. The third bedroom that has two twin beds, which be converted into a king bed. There's also a twin trundle bed in this room. Please note that we are on well water spring water dispenser is provided. We occasionally use this property with our young sons, so some toys and kids' equipment are provided. Guest access Entire place Other things to note We just took a three-month break from airnb (September to December, so there are not reviews during this period). We are on well water and filtered water is offered at the kitchen sink on the cold side. We also provide a Spring water dispenser. Registration Details 000754

Quiet Getaway in Waterfront Community

Welcome to this spacious, freshly updated 4BR/2BA North Beach home! Enjoy 1,920 sq ft of comfort with furnished living spaces and in-unit laundry. The remodeled lower level offers a private suite with walkout. Outside, relax on two large decks, a fenced yard, a cozy fire pit, and ample parking. The perfect coastal getaway!

4BR North beach Home w/ Decks, Firepit & Game room

Indulge in this beautifully appointed 4-bedroom, 2-bathroom house 6 blocks from the Chesapeake Bay boardwalk! Revel in a chef's kitchen, open living area, screened porch, with separate workspace. Relax by the heated saltwater pool BBQ on the deck or gather around the cozy firepit. Walk to restaurants and enjoy live music experiences, the local wine bar or beer, conveniently close to local wedding venues. This North Beach gem guarantees an unforgettable stay! Guest access You will have exclusive access to the entire house, driveway, backyard, firepit, pool, deck and patio area! Owner may enter yard to service pool as necessary and will provide guest notice. Access to the detached garage and detached owner-occupied apartment are owner accessible only. Other things to note Additional rules 1. Absolutely NO Smoking, Vaping or drugs of any kind, including Marijuana are allowed on the premises. This includes inside the house, on the screened porch or the front, back, side yards or driveways. This rule will be strictly enforced. 2. No pets of any kind are allowed on the premises at anytime. Of course certified Service Animals are always welcome. 3. Pool hours are from 8:00 am until 10:00 pm daily. A separate agreement including pool rules and regulations must be fully executed prior to the commencement of any stay.

Stunning North Beach Getaway w/ 
Inground Pool

Spring get away retreat close to Annapolis!

Welcome to our newly updated 4 bedroom, 3.5 bath coastal beauty w/beautiful views of the South River! Situated in a quiet neighborhood within 45 minutes of DC & 15 minutes from Annapolis & the Naval Academy, our home has everything you need to relax and enjoy time with friends and family. Our home boasts of beautiful natural light and water views throughout the home. The 3 seasons porch and large front yard provide additional spaces for entertaining. The space Our newly updated 4-bedroom home is designed with spacious living and effortless entertaining in mind. Step inside to find expansive rooms filled with natural light, including an open-plan living and dining area perfect for gatherings. The gourmet kitchen boasts modern appliances and flows seamlessly to both indoor and outdoor entertainment areas. Outside, a large patio and landscaped yard make it easy to relax or host guests, all while enjoying breathtaking views of the water. The small beach/club house in front of house is part of the Selby Bay Club and is private, however, there are multiple public beaches in the area, the closest 2 Triton and Mayo are less than 10 minute drive from house. Where you will sleep: Each bedroom offers comfort and privacy. The first floor bedroom features a master suite that has it's own wet bar and sitting area that comes with a day bed for seating or to accommodate two extra guests. On the second floor you will find three additional bedrooms. Bedroom 1 comes with a queen size bed. Bedroom 2 comes with two single beds and plenty of space to stretch out. Bedroom 3 is a second floor master suite with its own private deck, for you to sit out and watch the sunsets or have your morning cup of coffee. This bedroom provides a luxurious retreat with water views. Guest access During your stay, you and your guests will have exclusive access to all areas of the property. Please exercise caution near the water. The community beach is for residents only. Please do not park vehicles in the community beach parking area. Other things to note Keep noise to a minimum between 10:00pm and 8:00am. This is to help us maintain the peaceful atmosphere for all of the guests at the property and a peaceful presence within the neighborhood. Registration Details 000989

Edgewater's Shelby on the Bay

PRICE IMPROVEMENT Welcome to this HIDDEN GEM of Anne Arundle County. Fully Renovated Coastal Retreat in Deale with Rare Two-Level Workshop.  Houses this big at this price point don’t come up for sale very often.  Experience the best of coastal living in this beautifully renovated Deale retreat, where timeless charm meets modern convenience. From the inviting wrap-around front porch to the expansive rear deck with peaceful water views, this exceptional property is designed for both relaxation and entertaining.  At the heart of the home is a stunning, fully remodeled kitchen featuring new cabinetry, updated countertops, and stainless-steel appliances. The open-concept floor plan flows seamlessly into the spacious family room, where soaring ceilings and abundant natural light create a warm, welcoming atmosphere. Easy access to the rear deck makes indoor-outdoor living effortless.  Thoughtful updates throughout include renovated bathrooms, fresh interior paint, new carpeting, updated finishes, and an EV charging station, ensuring the home is truly move-in ready. Generously sized bedrooms provide comfort and flexibility, while the private upper-level primary suite offers a peaceful retreat complete with its own balcony—perfect for enjoying morning coffee or evening sunsets.  Step outside to your private backyard oasis. The expansive deck overlooks tranquil water views and features a swim spa ideal for exercise, relaxation, or entertaining guests year-round. Enjoy the serenity of the beautifully landscaped grounds, including a peaceful koi pond that creates the perfect setting to unwind.  A rare and highly desirable feature is the large two-level workshop—an incredible space for hobbyists, craftsmen, boat enthusiasts, artists, or anyone seeking substantial storage and workspace. Whether used as a workshop, studio, equipment storage area, AIR BNB or creative retreat, the possibilities are endless.  Located just minutes from the Chesapeake Bay, local marinas, waterfront dining, and all that Deale's coastal lifestyle has to offer, this exceptional property combines modern updates, versatile space, and waterfront charm in a way that's rarely available. HOME WARRANTY INCLUDED

5929 Deale Beach Rd Deale, Maryland

$107,124

Annual Revenue

Investment Value Over Time