Welcome to this stylish and spacious 3BR 3.5 BA home situated in the heart of historic downtown Annapolis.  Newly renovated, this charming retreat is just steps away from shopping, dining and a public parking garage.  Walk to the USNA & the iconic City Dock (Ego Alley). The home features 3 private suites - 2 king bedrooms with private baths (1 on ground floor), & a queen bedroom with an adjoining daybed room (perfect for kids). A fully stocked kitchen complete with wine cooler, W/D and patio.

The Gloucester House

Experience the Difference: Professionally Managed by iTrip Annapolis The space Step into Annapolis history at this beautifully restored three-story cedar home. Built in the late 18th century, this property is recognized in the Historic District’s National Registry as one that “embodies the distinctive characteristics of a period.” Over the centuries, it has served as a shoemaker’s store, an inn, and the residence of an Italian immigrant who played in the U.S. Naval Academy band. Later converted into three apartments, the home was thoughtfully restored in the 1970s and newly-renovated into the elegant single-family dwelling it is today. Main Level Living Enter through the front door to a spacious family room, perfect for relaxing after a day of exploring downtown Annapolis. With a plush queen sleeper sofa and a large flatscreen TV, this room doubles as a cozy gathering space or extra sleeping option. Original wood floors run throughout, creating warmth and character. The Main level, and all 3 bedrooms, each have their own flatscreen TV. The adjoining dining room features a restored built-in hutch and seating for six. The full kitchen is stocked with everything needed for preparing meals at home, while a convenient powder room completes the main floor. From the kitchen, step outside to the fenced-in backyard with Adirondack chairs and a propane grill—an intimate spot for morning coffee or evening cookouts. The home is located just a 2-minute walk to City Dock, Main Street, State Circle, and the Naval Academy entrance. Parking: No on-site parking. One dedicated space is provided in a nearby garage (10-minute walk). The garage charges a one-time $5 per vehicle service fee. Please contact us for parking details. SLEEPING ARRANGEMENTS 3 BR / 3.5 BA / Sleeps 8: Top Floor King Suite: King Bed Ensuite Full Bath with double vanity, shower/bathtub combo and walk-in closet 2nd Floor King Suite: King Bed Ensuite Full Bath with stand-up shower 2nd Floor Queen Guestroom Queen Bed Full Bath in the Hall with shower/bathtub combo Main Level Full Sleeper Sofa Powder room on Main Floor and shared Full Bath in the Hall on the 2nd Floor Amenities & Highlights Private fenced yard with Adirondack seating and propane grill Fully equipped kitchen Dining table with seating for 6 WiFi & big screen TVs in every bedroom and the Family Room Luxury linens & complimentary starter toiletries Washer & dryer inside the home Contactless check-in via coded front door entry Non-smoking property Property Distance to: - U.S. Naval Academy – 2 blocks - Washington, DC – 30 miles - Baltimore - 25 miles *Amenity & Supplies starter pack, coffees and 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 Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking/no pets. Please respect the neighbors and neighborhood. Check-in time: 4:00 pm Check-out time: 11:00 am Blending centuries-old charm with modern amenities, this property offers the ideal downtown Annapolis getaway—whether you’re visiting for the Naval Academy, a weekend retreat, or a family celebration. 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 002190_2025

Boutique Home 2 blocks to City Dock w Parking

Beautiful Remodeled Townhome ! We have thought of everything you will need for an amazing stay. Fully loaded kitchen , 3 and 1/2 Baths , Wonderful Upgraded Mattresses that will ensure a great nights sleep, Big screen TV's Back yard courtyard with gas firepit. And the best part....... Walking distance to Downtown Annapolis with Shopping , Dining and much more bring the whole family to this great place with lots of room for fun. The space Primary Bedroom has a King Size bed and Full bath, 2nd Bedroom Queen Bed , 3rd Bedroom twin Bunkbeds and hall bath , Basement beds - Queen Sleeper Sofa and a Queen Murphy Bed. Basement has full bath Guest access Entire Home . Other things to note Parking Pass provided. Additional pass available upon request.

Beautiful Downtown Annapolis Townhome!

Beautiful modern 3-level single-family home with 3 bedrooms and 3 1/2 baths. Back-up generator is provided. Located in Eastport, Annapolis. Totally renovated in 2019. Enjoy the heated and salt added pool. THE POOL IS OPEN FROM MID-MAY TO LABOR DAY. PLEASE CONTACT US FOR OPEN EXCEPTIONS AHEAD OF TIME. Minutes to downtown. Perfect for Commissioning Week, Naval Academy activities and Annapolis sailing and boat shows. Minutes to restaurants, pubs and Chesapeake Bay sightseeing. The space Designer's modern house. Large master bedroom with queen-sized bed and two additional bedrooms on the upper floor. One of the additional bedrooms has a queen-sized bed and the other has 2 twin-sized beds. Additionally, two pull-out queen sized beds on 2 different levels. TV in living room and family room. Spacious garage. Enjoy the pool in the back which has privacy fence. Guest access Guests have access to the full property. We ask that guests be responsible for ensuring the safety of their children while swimming. Both the garage door and the front door are accessible by code. Pool will be available after5/1/2026 Other things to note SPECIAL FOR NAVAL COMMISIONING WEEK Vin 909 Winecafe is located within easy walking distance and local wineries include Cooper's Hawk Winery and Restaurant and Great Frogs Winery.

Beautiful house in the best location!

Built in 2019 with open spaces and happy places on historic Eastport Peninsula. A fresh take on coastal contemporary with front & back porches just steps from the Severn River & Spa Creek. Easy to enjoy the salty vibe with short walks to water access areas as well as Eastport's best local pubs and restaurants; or head over the Eastport bridge to downtown Annapolis and the Naval Academy - also accessible by water-taxi, rental boats & paddle-boards... A great NEW place in a great OLD place!!! The space Hi-quality construction with premium finishes throughout; Light & airy modern beach house design. Ground floor - Main space includes a large open family-room / kitchen / dining area off rear porch. This is already proving to be a great gathering space with high capacity.. The sitting area has a 113" sofa, (2) swivel chairs, and a large suede bench / coffee table / ottoman.. Large-screen TV above gas fireplace is fully connected to cable and wifi. 4 counter-stools fit comfortably at the large island adjacent to dining area with a seagrass & glass round table 2 upholstered chairs and 4 new wicker chairs that can be moved around as needed. A high chair is available if necessary, but the closed-in counter stools do a good job in a pinch - for toddlers. Another living area off the front porch includes a leather sofa / daybed and 2 upholstered rocking chairs. This area is planned to be a bar & lounge by next spring, but the chairs offer a comfy reading spot for now. The ground level also includes a powder room. Upper level - 3 Bedrooms with 2 Bathrooms; Master bedroom with large deck to the rear (winter water views of the Naval Academy), high end private bathroom, plus new king-sized bed, console, big screen 4K TV (fully connected) and solar shades; 2nd bedroom opens to another deck and includes a new king sized bed with "sofa backrest", large closet and big screen smart TV suitable for app-based programming (netflix, prime, youtube..) and blackout shades; 3rd bedroom includes queen sized bed + loft bed, large closet and blackout shades. 2nd and 3rd bedrooms share a generous hallway bathroom pictured in the photo gallery. Newly finished basement - Finished basement w/ XL pit-sofa and small chairs. Wide open space w/ available queen size mattress and ping pong table . Full bathroom with tub/shower combo. *Also available: air mattress, full-sized crib, pack & play, kids books and toys... Guest access All of the space above ground will be accessible with the possible exception of one of the pantry closets and a storage area in the lower level. The remainder of the lower level is now fully finished and available.

Moose’s Happy Place

Experience the Difference: Professionally Managed by iTrip Annapolis The space This charming 3-BR, 2.5-BA townhome is just a 1/2-block from the city dock and is a luxurious vacation getaway in the heart of the historic district of Annapolis. Built in 1881, this townhome has been completely renovated, with beautiful wood floors, an open floor plan and every modern convenience. Entertain in the open kitchen that flows seamlessly into the dining room and living room and out to the private back patio. There are 3 bedrooms and 2 baths upstairs, with sleeping for 5 in the 2 Queen beds and 1 Twin. The en-suite Queen bedroom also has private balcony. On the main level is room to sleep up to 2 adults or 4 more kids on the family and living room's Queen sleeper sofas. Take advantage of the rich culture, history, shopping and entertainment of Annapolis. The State Circle, the Annapolis Yacht Club and the Naval Academy are all within two blocks. Ego Alley and the historic William Paca, James Brice and Hammond-Harwood houses are a five-minute stroll. Park your car and experience all of downtown Annapolis within easy walking distance. Or just stay in and enjoy the three smart TVs, high-speed Wi-Fi and cable TV. Colonial charm. Rich history. Comfort and convenience. SLEEPING ARRANGEMENTS 3 BR / 2.5 BA / Sleeps 7-9: Queen Suite (sleeps 2): - Second Floor - Queen Bed - En-suite full bath Guest Bedroom (sleeps 2): - Second Floor - Queen Bed - Full Bath in the Hall Twin Guest room (sleeps 1): - Twin Bed - Full Bath in the Hall Family Room (sleeps 1-2): - Main floor - Queen Sleeper Sofa - Full Bath in the Hall upstairs or half bath on main floor Living Room (sleeps 1-2): - Main floor - Queen Sleeper Sofa - Full Bath in the Hall upstairs or half bath on main floor HIGHLIGHTS: - Private fenced-in back patio with gas grill (propane provided) - Balcony off Queen suite - Full gourmet kitchen - Dining room table seats 8 - WiFi - Multiple Flatscreen TV's - Luxury linens, complimentary toiletries Starter Kit, and boutique-level service - Washer & dryer located inside the home - No pets - Keyless entry. Drive straight to your rental home and enter the door with an electronic lock code. Property Distance to: - U.S. Naval Academy – 2 blocks - Washington, DC – 30 miles - Baltimore - 25 miles * Amenity & Supplies starter pack, coffee and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going. * All beds are ready made for you with freshly laundered sheets & towels. House Rules Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking/no pets. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind. Check-in time: 4:00 pm Check-out time: 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 STR 144109

History & Charm Catch 22 Walk to USNA & City Dock

Experience the Difference: Professionally Managed by iTrip Annapolis The space How many homes in Downtown Annapolis have 4 Bedrooms with 4 Baths (3 of which are en-suite)?! Just 1-2 blocks from the Annapolis waterfront, the State Capitol, restaurants, shopping and the Naval Academy, this cherished property is registered with the Historical Society of Annapolis (originally home to “Sam’s Grocery”—a beloved neighborhood corner-store). After Sam's Grocery closed up shop in the eighties, the building was converted into a bed and breakfast, most recently called the "Chez Amis Inn". Now its a unique rental home and you have the entire place to yourself! Each of the three upstairs bedrooms has been named by the former innkeepers and they are a tribute to the State Capitol's history. On the main floor you will find the Treaty of Paris Room-a library with an en Suite bath and Full size Sleeper sofa. **Parking is not on premises!! A dedicated parking spot at nearby garage (15-minute walk from the house) is provided. Please contact us for details. SLEEPING ARRANGEMENTS 4 BR / 4 BA / Sleeps 7 The State House Bedroom: -King Size Bed -En Suite Bathroom -Extra Pedestal sink in bedroom -Wall mounted TV The Law Library: -En Suite Bathroom -Queen Bed -Wall mounted Flatscreen TV The Annapolis Room: -Queen bed -Private Bathroom in Hall -Wall mounted Flatscreen TV The Treaty of Paris Den: -Multi-functional Family Den and Bedroom -Full Size Sofa Bed -En Suite Bathroom -Wall mounted Flatscreen TV *The full-size sofa bed may be tight for 2 guests. There is also a portable Twin cot located in the home. HIGHLIGHTS: Stocked kitchen with every appliance - large and small - you would need. -Fully-stock Bar in the Library - BYO liquor/spirits -Kitchen Coffee bar seats 2 -Dining room table seats 8 -Outside seating for 4 -High Speed Internet and WiFi -Big Screen TV in Main Floor Library (Flatscreen TVs in every Bedroom) -Luxury linens, complimentary toiletries and paper product Starter Kits, and boutique-level service. -Washer & dryer located inside the home. -Dogs allowed with $150 non-refundable pet deposit paid prior to check-in. -One Garage Parking Spot located 0.7 miles from the home. -Keyless entry. Drive straight to your rental home and enter the front door with an electronic lock code. Property Distance to: -U.S. Naval Academy – 1 block -Washington, DC – 30 miles -Baltimore - 25 miles * Amenity & Supplies starter pack, coffees and 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 Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking. Be respectful of the house and contents - it is someone's home and the owners do come back from time to time to stay in their property. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind. Check-in time: 4:00 pm Check-out time: 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 STR-144960

Walk to USNA, Main St w Free Off-site Parking

Steps away from the Naval Academy, St. John's College, State House, City Dock, Yacht Club, St. Mary's Church and local restaurants/shops. This historic 3 story / 3 bedroom house is perfect for a large group (w/pets) visiting Annapolis. -Covered front porch, private patio and hot tub -2 min walk to Gate 1 @ USNA The space Floor by floor configuration: 1st floor - Living room with sleeper sofa, dining room (seats 6), kitchen, powder room (1/2 bath) 2nd floor - Master bedroom (King sized bed) w/TV, 2nd bedroom (King sized bed), full bath 3rd floor - Loft style space with 3x twin beds w/ 50" TV Outside - Front porch with seating and swing, back patio featuring hot tub, table, and BBQ grill Guest access Guests have access to the entire house and backyard except for locked storage closets and unfinished basement. Complimentary laundry access for guests staying 4+ nights. Other things to note To help ensure a smooth, secure, and enjoyable stay for all guests, please review the following important information before booking: Check-In & Identity Verification Policy All reservations require the primary guest (the booker) to complete a secure online check-in process prior to arrival. This includes: -Uploading a valid, unexpired government-issued photo ID -Uploading a selfie to confirm identity -Reviewing and signing our rental agreement This process is similar to hotel check-in and is required because we do not typically have staff on site. Check-in instructions will only be provided once this process is complete. If you would like to review the rental agreement before booking, please feel free to contact us. In some cases, we may also request a security deposit and/or apply a damage waiver fee in accordance with booking channel policies. * It typically takes ~1 hour to screen a guest after they book this property and could take several hours if we are busy before we are able to provide them with check-in information. If you make a last minute reservation, we ask you to please be patient and please do not expect to gain access to the property immediately. Guest Count & Occupancy Policy Each listing includes a maximum number of guests based on unit type and local regulations. Additional guests are welcome for an added nightly fee: -2 & 3 bedroom units: $35 per guest, per night after 4 or 6 guests, respectively Please ensure your guest count is entered accurately at booking. We will confirm the number of guests after reservation. If the guest count changes, pricing may be adjusted accordingly. For safety and compliance purposes, exterior security cameras are used to verify occupancy. Unreported additional guests may result in additional charges. Pet Policy This is a pet-friendly property. While our cleaning team is thorough, guests with severe pet allergies should be aware that dogs, cats, or other animals may have stayed in the space previously. Pet fees: $30 per night, per pet $150 per week, per pet $300 per month, per pet Pet fees are included in the accommodation rate as long as you choose the appropriate quantity of pets when completing a booking. We confirm this with all guests post booking confirmation. Local Reservation Policy Reservations under 7 nights from guests residing in the local area may be subject to cancellation at our discretion. We handle exceptions on a case-by-case basis. Early Check-In & Late Check-Out Policy Early arrivals and late departures are not guaranteed and must be approved in advance. If approved, the following fees apply: -Up to 1 hour: $100 -1–2 hours: $200 -2–3 hours: $300 -3+ hours: $400 or the cost of an additional night (whichever is greater) Please do not assume availability without confirmation. Smoking Policy Smoking is not permitted anywhere on the property, including indoor and outdoor areas. If evidence of smoking is found, an additional cleaning fee of $500 will be applied in accordance with the booking channel's cleaning and damage policies. Special Request Policy Requests for items such as pack-n-plays, high chairs, or other non-standard amenities should be submitted at least 7 days before check-in to ensure availability. Requests made closer to arrival will be accommodated if possible but cannot be guaranteed. We understand that this is a detailed list, and we truly appreciate you taking the time to review it. These guidelines help us maintain a safe, well-cared-for property and ensure a great experience for every guest. Our goal is always for you to feel comfortable, welcome, and well taken care of during your stay.

Historic Row Home | Hot Tub - 1 Block from Gate 1!

Ideally located between the vibrant West Street and the historic Main Street, our downtown Annapolis home offers easy access to restaurants, shops, bars etc. We’ve carefully furnished the space to create an inviting maritime environment with 3 bedrooms and 3.5 bathrooms (en-suite) comfortably accommodating up to 7 guests. The high ceilings give an open and airy feel, while the inviting front porch offers a cozy east coast touch. The private backyard is perfect for the summer months . The space We offer an open floor pan with 3 bedrooms , 3.5 baths and five beds .. USNA family owned Guest access Whole house Other things to note USNA family owned. We offer a paid parking space in a nearby city owned Gotts garage ( about 2 blocks away ) Popular Walking distances West st shopping and dining - 1 min Parking garage - 2 min Church circle - 2 min Main St shopping and dining - 3 min Annapolis City Dock- 7 min USNA Gate 1- 9 min Fireplace is decorative

Darling on Dean Street- Nautical home w parking

Experience the Difference: Professionally Managed by iTrip Annapolis The space Take a stroll along the brick-lined sidewalks of Prince George Street in the Historic District and to this fully-renovated late 1800s charmer with touches of historical elegance. On the first level, relax in the large living room with a cozy double-sided gas brick fireplace that is open to the dining room. The upgraded kitchen with granite countertops and stainless steel appliances is fully-stocked for the gourmet chef. Cozy up in the back Den that doubles as a bedroom with a new pullout Queen sofa, a half-bath and a curtain to close for privacy. Head upstairs to the 3 Queen bedrooms and 2.5 more baths. The en-suite Queen bedroom has a spa-like bathroom complete with a custom vanity and a relaxing steam shower. The second bedroom converts between a Full bed and a desk with great natural lighting and leads to the balcony that overlooks the St. Johns College front lawn and the beautiful USNA chapel. The third level has another private suite with a Queen bed a private powder room. But what's really breathtaking is the backyard retreat: enjoy sitting around the fire pit on the Adirondak chairs, grilling and eating al fresco around the dining table for 6 or lounge on the cozy outdoor love seats and sofa. The location of this home is prime as you are within walking distance to everything Downtown Annapolis has to offer from entertainment, and beautiful water views, Naval Academy, St. Johns College, and the state capital building. **Parking is not on premises!! A dedicated parking spot at nearby garage (10/15-minute walk) is provided. Please contact us for details. SLEEPING ARRANGEMENTS 3 BR / 2 Full/2 Half Baths / Sleeps 8: Master Bedroom with En-Suite Full Bath: - Second Floor - Queen Bed - Custom spa shower walk-in shower with steam shower Convertible Full Bedroom with Balcony: - Second Floor - Full bed that converts to a desk - Private Balcony - Full Bath in the Hall 3rd Floor Loft: - Queen Bed - Powder Room Den/Bedroom - Main floor - Flatscreen TV - Sofa Queen Bed - Powder room - Privacy curtain HIGHLIGHTS: - Spacious gourmet kitchen - Gas fireplace - Dining room table seats 6 - Eat-in kitchen seats 2 - Spacious outdoor living, dining and fire pit area. - High-speed WiFi - Weber BBQ propane Grill - Big Screen Smart TVs - Luxury linens, complimentary toiletries Starter Kit, and boutique-level service - Washer & dryer located inside the home - One parking spot in off-site garage. - Keyless entry. Drive straight to your rental home and enter the front door with an electronic lock code. Property Distance to: - U.S. Naval Academy – 3 blocks - Washington, DC – 30 miles - Baltimore - 25 miles * Amenity & Supplies starter pack, coffee and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going. * All beds are ready made for you with freshly-laundered sheets & towels. House Rules Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking or pets. Please respect the neighbors and neighborhood. No parties or events of any kind. Check-in time: 4:00 pm Check-out time: 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 STR22-145128

Historic Hideaway Steps to USNA w Patio & Parking

Experience a beautifully restored and well appointed Greek Revival home on a calm street directly facing the U.S. Naval Academy and steps from the Navy Chapel and Gate 3. This rare property blends historic character with high-end modern updates and chic, boutique hotel-like furnishings, offering a relaxing yet central retreat in downtown Annapolis. The space Thoughtfully renovated under architectural guidance, this impeccable historic home features elegant details, abundant natural light, and a seamless layout designed for comfort and great for entertaining. Main level: Gather in the living room with TV, dining room that seats 6, luxurious kitchen well-stocked for meals, coffee bar, breakfast table, and counter seating. A full bathroom with washer/dryer also on this level. Check out the outdoor patio and lovely backyard with grill and seating. Upstairs: Bedroom 1: King bed and ensuite full bathroom Bedroom 2: Queen bed with TV Bedroom 3: Queen bed, TV, large windows overlooking backyard, spacious patio. (elevator in this room- elevator is not for use by guests without prior approval) Bath 2: Ensuite for primary bedroom- standing shower Bath 3: Conveniently located in the hall shared by bedrooms 2 and 3, this bathroom contains a bathtub with shower. Outdoor space: Private patio/backyard with cafe table seating, 2 Adirondack chairs, and a gas grill for our guests to use! License #: RENT-002665-2025 Other things to note To help ensure a smooth, secure, and enjoyable stay for all guests, please review the following important information before booking: Check-In & Identity Verification Policy All reservations require the primary guest (the booker) to complete a secure online check-in process prior to arrival. This includes: -Uploading a valid, unexpired government-issued photo ID -Uploading a selfie to confirm identity -Reviewing and signing our rental agreement This process is similar to hotel check-in and is required because we do not typically have staff on site. Check-in instructions will only be provided once this process is complete. If you would like to review the rental agreement before booking, please feel free to contact us. In some cases, we may also request a security deposit and/or apply a damage waiver fee in accordance with booking channel policies. * It typically takes ~1 hour to screen a guest after they book this property and could take several hours if we are busy before we are able to provide them with check-in information. If you make a last minute reservation, we ask you to please be patient and please do not expect to gain access to the property immediately. Guest Count & Occupancy Policy Each listing includes a maximum number of guests based on unit type and local regulations. Additional guests are welcome for an added nightly fee: -2 & 3 bedroom units: $35 per guest, per night after 4 or 6 guests, respectively Please ensure your guest count is entered accurately at booking. We will confirm the number of guests after reservation. If the guest count changes, pricing may be adjusted accordingly. For safety and compliance purposes, exterior security cameras are used to verify occupancy. Unreported additional guests may result in additional charges. Pet Policy This is a pet-friendly property. While our cleaning team is thorough, guests with severe pet allergies should be aware that dogs, cats, or other animals may have stayed in the space previously. Pet fees: $30 per night, per pet $150 per week, per pet $300 per month, per pet Pet fees are included in the accommodation rate as long as you choose the appropriate quantity of pets when completing a booking. We confirm this with all guests post booking confirmation. Local Reservation Policy Reservations under 7 nights from guests residing in the local area may be subject to cancellation at our discretion. We handle exceptions on a case-by-case basis. Early Check-In & Late Check-Out Policy Early arrivals and late departures are not guaranteed and must be approved in advance. If approved, the following fees apply: -Up to 1 hour: $100 -1–2 hours: $200 -2–3 hours: $300 -3+ hours: $400 or the cost of an additional night (whichever is greater) Please do not assume availability without confirmation. Smoking Policy Smoking is not permitted anywhere on the property, including indoor and outdoor areas. If evidence of smoking is found, an additional cleaning fee of $500 will be applied in accordance with the booking channel's cleaning and damage policies. Special Request Policy Requests for items such as pack-n-plays, high chairs, or other non-standard amenities should be submitted at least 7 days before check-in to ensure availability. Requests made closer to arrival will be accommodated if possible but cannot be guaranteed. We understand that this is a detailed list, and we truly appreciate you taking the time to review it. These guidelines help us maintain a safe, well-cared-for property and ensure a great experience for every guest. Our goal is always for you to feel comfortable, welcome, and well taken care of during your stay.

Luxe Row Home Steps to USNA Gate 3!

Experience the Difference: Professionally Managed by iTrip Annapolis The space This is a unique home like none other in downtown Annapolis. Originally the Eastport Volunteer Fire Company, founded in 1864, Eastport native Art Tuers joined the company in 1949 at the age of 16. The largest fires Tuers and the dozen or so other active volunteers battled were at the Carvel Hall Hotel in 1961, in the building which was later restored as the William Paca House! Located across the Annapolis harbor, the "Maritime Republic of Eastport" offers unique views of the Naval Academy, the Chesapeake Bay and the Annapolis Marina. Located a short walk from the home is "Eastport Restaurant Row", serving up fresh seafood along with great steakhouses, it’s the perfect place to get away from the bustle of downtown. It’s also one of the only areas where you can dine right alongside the water, enjoying a great meal while catching the sun dipping behind Annapolis. When entering the home on the first floor, you will be welcomed by the original brick floors in the foyer mudroom. Take the wooden staircase up to the second floor where you will find the 9-foot ceilings over the open kitchen, dining and family room which opens onto a fully-furnished screened-in porch with a gas fireplace. In addition to the living space, the 2nd floor has 2 En Suite bedrooms: the Master features its own large balcony facing the quiet neighborhood street. To find the living sleeping space on the first floor, either walk down the spiral staircase from the family room or enter from the garage door off the 1st floor entrance. The 1st floor has a full living/bedroom space with a queen bed, sleeper sofa and full bath and a 2nd living space/rec room with a kitchenette in the garage. All 3 living spaces have big-screen TVs; all bedrooms have their own TV. SLEEPING ARRANGEMENTS 3 BR / 3 BA / Sleeps 8: Master Bedroom: - Second Floor - Queen Size Bed - Full En Suite Bath with double vanity and large stand-up shower - Flat screen TV - Balcony Bedroom 2: - Second Floor - Queen Size Bed - Full En Suite Bath with stand-up shower (has 2nd entrance into the hallway) - Flat screen TV 1st Floor Bedroom/Living Room: - Queen bed - Queen sleeper Sofa - Flat Screen TV HIGHLIGHTS: - Covered balcony off the Master Bedroom - Screened-in patio off the Family Room with brand new furniture - Breakfast Bar seats 3 - Spacious gourmet kitchen - Dining room table seats 6-8 -Additional furnished rec room in garage with 3rd living space, kitchenette and TV - WiFi - Big Screen TVs in each living and bedroom - Luxury linens, complimentary toiletries Starter Kit, and boutique-level service - Unrestricted Street Parking - Washer & dryer located on the first floor - Elderly and guests with mobility issues may want to inquire about the steep staircase and/or may want to consider other accommodations. - Keyless entry Property Distance to: - U.S. Naval Academy – 1.5 miles - Washington, DC – 30 miles - Baltimore - 25 miles *Amenity & Supplies starter pack, coffees and 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 Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking; no pets unless requested and $150 deposit paid prior to check-in. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind. Check-in time: 4:00 pm Check-out time: 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 144920

Historic Eastport Firehouse w Parking, Dogs OK

Historic 1885 row home two blocks from Main Street and steps from the U.S. Naval Academy. Three bedrooms across three floors with a king master, two queens, and a twin - sleeps 9. Pet-friendly (dogs under 30 lbs welcome) with covered off-street parking half a block away. Walk to Annapolis' restaurants, shops, and waterfront without ever moving your car. The space Enter through the white gate to a private back patio, then into the renovated kitchen - modern appliances, sleek countertops, and natural light from every window. The living room is just beyond, with plush seating and a sofa bed for extra sleeping. Second floor: king master bedroom and a queen bedroom share a full hallway bathroom. Third floor: queen bed, twin bed, and its own attached bathroom with stand-up shower - great for a family with kids or guests who want more privacy. The home was built in 1885 and is named for the owner's great-grandfather, a founding figure in Annapolis' fire departments. You'll feel that history in the architecture while enjoying fully modern finishes throughout. Guest access Upon arrival, walk through the white gate on the left side of the home to enter the courtyard, and then proceed through the back door to enter the house. Other things to note ** Parking Information for Your Stay:** We have a dedicated parking spot for you during your stay! Parking is available at the Noah Hillman parking garage, just a 1-minute walk from the home. You can use your car's flashers while unloading your luggage, and then head to the garage once you're finished. Additional Parking: If you have an additional vehicle, you may purchase an extra parking spot in the same garage before parking. A QR code is available in the garage for payment instructions. Vehicles parked without payment or in unauthorized areas may receive a ticket or be towed **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.** **Small pets allowed after paying the pet fee $150 – maximum 30 lbs. Exceptions are made on special request.** **Early Check-In & Late Check-Out Policy We offer early check-in and late check-out upon request, subject to availability. One hour is complimentary However, a fee applies as follows: 	•	Early Check-In before 3pm for an additional fee of $50 to be paid before check -in 	•	Late Check-Out after 12pm for an additional fee of $50 to be paid before check-out Please request in advance so we can confirm availability.**

Historic Annapolis Home | 2 Blocks to Main St

Discover 'The Crabby Patty,' a spacious 3-BR, 2.5-BA home in the heart of downtown Annapolis. Blending modern comfort with historic charm, this stylish retreat is perfect for families or groups. Enjoy a fully equipped kitchen, a dedicated workspace, and a prime location just steps from the US Naval Academy and city waterfront. Walk to everything from this unforgettable getaway. The space Welcome to our vacation rental nestled in the heart of Downtown Annapolis. Immerse yourself in the rich history and vibrant culture of this charming city. Our inviting 3-bedroom, 2.5-bathroom home is a spacious retreat, thoughtfully designed to provide an unforgettable vacation experience. The open-concept living area invites you to relax, filled with stylish furnishings and ample natural light. Prepare meals in the fully equipped kitchen, complete with modern stainless steel appliances, before gathering around the large wooden dining table. After a day of exploration, rest and recharge in our comfortable bedrooms. Where you will sleep: * Bedroom 1: Your spot to relax,a cozy room with a very comfortable plush bed, ideal for a restful night * Bedroom 2: The perfect blend of comfort and productivity. This room features a dedicated workspace, ideal for those who need a quiet, cozy spot to work from home or study * Bedroom 3: Offers a fun and flexible sleeping arrangement with bunk beds. The home includes two contemporary full bathrooms upstairs and a convenient half-bathroom on the main level, all stocked with complimentary toiletries. Washer & dryer in-home STR22-145090 Guest access You will have private access to the entire home. For your convenience, we offer seamless self check-in with a smart lock. Other things to note We look forward to hosting you at 'The Crabby Patty' for an unforgettable Annapolis adventure! City of Annapolis STR License: STR22-145090 Self check-in with a smart lock. Access code will be provided prior to your arrival.

Crabby Patty-Historic Downtown 3BR- Walk to USNA

Experience the Difference: Professionally Managed by iTrip Annapolis The space Elegant Historic Home with Private Parking in the Heart of Downtown Annapolis Welcome to your beautifully restored retreat—once two separate homes, now thoughtfully combined into one expansive and stylish residence in the heart of Historic Annapolis. Enjoy the rare convenience of two private and secure parking spaces, and settle into a home that blends character, comfort, and location. Main Living Spaces On the main floor, guests will find multiple areas to relax and gather: Formal dining room for celebratory meals Comfortable living room perfect for conversation or quiet moments Open-concept kitchen and family room with ample seating and direct access to the covered patio and fenced-in backyard Step outside to a covered patio with lounge furniture, and enjoy evenings in your private backyard oasis, complete with stone pavers and a charming front porch swing. Sleeping Arrangements (Sleeps 7 adults + 1 infant | 3 Bedrooms | 2.5 Baths): King Suite (2nd Floor): King bed, oversized en-suite bath with jacuzzi tub, walk-in shower, dual vanities, and a custom walk-in closet Queen Bedroom (2nd Floor): Queen bed, shares access to a full hall bath Bunk Room (2nd Floor): Twin over Full bunk bed, full-size crib, and shared full hall bath Home Highlights Gourmet kitchen with generous prep space and modern appliances Two secure parking spaces (The garage height has 7 foot clearance; width may limit larger SUVs) Dining table seats 10–12—ideal for large family meals or entertaining Surround sound speakers for immersive music and movie nights Smart TVs and high-speed WiFi Main level extra large laundry room with full-size refrigerator washer, dryer, drying racks, and storage Luxury linens and starter toiletries provided for a boutique-level experience Keyless entry for seamless and secure check-in Location, Location, Location Annapolis Harbor & Main Street – 3 blocks away U.S. Naval Academy – 10-minute walk Restaurants, boutiques, and bars – All within a 5-minute stroll Washington, DC – 30 miles | Baltimore – 25 miles No parties or smoking permitted. Quiet hours must be observed to respect the neighborhood. Check-in: 4:00 PM | Check-out: 11:00 AM Whether you’re here to explore Annapolis’ historic charm, celebrate with friends, or attend a Naval Academy event, this spacious and well-appointed home is the perfect downtown base. 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 002200

Luxury Historic Annapolis Home with Parking

Experience the Difference: Professionally Managed by iTrip Annapolis The space Enjoy a piece of Annapolis history! Nestled at the end of a row, this circa 1879 home has the perfect blend of historic cedar shake charm on the outside combined with a surprisingly modern interior. The renovated kitchen with its exposed brick chimney, beautiful cabinets, granite countertops and breakfast bar overlooks the sunken great room with walls of windows and cathedral ceilings. Celebrate your Happy Hours on the spacious screened porch overlooking the private backyard. Back inside is a dining room with seating for 8 and bright living room in the front of the home with a new Queen sleeper sofa. There is also a powder room and full laundry room located on the main floor. Head upstairs to the 3 oversized bedrooms and 2 bathrooms. The 2 guest bedrooms on the 2nd floor share the unique full bath in the hall, with separate shower/bath and double vanity/toilet rooms. The third-floor suite has a Queen bed, its own private full bath and even a delightful peek-a-boo view of the Maryland State House. Located one block to the quiet waters of Spa Creek and 2 blocks to Main Street, this home is just steps away from downtown shopping, restaurants, parks and historical sites, the Naval Academy and the Maryland State House. *Parking: No on-site parking. One dedicated space is provided in a nearby garage (10-minute walk). The garage charges a one-time $5 per vehicle service fee. Please contact us for parking details. SLEEPING ARRANGEMENTS 3 BR / 2.5 BA / Sleeps 8: 3rd Floor Suite: - Queen Bed - Full ensuite bath with stand-up shower King Bedroom: - 2nd Floor - King Bed - Full bath in the hall with standup shower and soaking tub, double vanity Full Bedroom: - 2nd Floor - Full Bed - Full bath in the hall with standup shower and soaking tub, double vanity Living Room - Main Floor - Queen sleeper sofa - Half bath on the main floor; shared full bath in the hall on the 2nd floor HIGHLIGHTS: - Large Kitchen overlooking the sunny sunken den - Breakfast bar in kitchen seats 2 - Dining room table seats 8 - Large screened-in porch - Private backyard - WiFi - Big Screen Smart TV's - 2 bicycles for guest use - Luxury linens, complimentary toiletries Starter Kit, and boutique-level service - Keurig and coffee pot with starter coffee and creamers - Washer & dryer located inside the home - Elderly and guests with mobility issues may want to inquire about the steep staircase and/or may want to consider other accommodations. - Keyless entry. Drive straight to your rental home and enter the code for the electronic lock on the front door. Property Distance to: - U.S. Naval Academy – 5 blocks - Washington, DC – 30 miles - Baltimore - 25 miles * Amenity & Supplies starter pack, coffee and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going. * All beds are ready made for you with freshly laundered sheets & towels. House Rules Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking/no pets. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind. Check-in time: 4:00 pm Check-out time: 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 STR22-145159

Historic Happy Home w Screen Porch & Parking

Experience the Difference: Professionally Managed by iTrip Annapolis The space Experience Historic Annapolis in Comfort and Style This charming 4-bedroom home sits in the heart of Historic Annapolis, just steps from Main Street. Perfect for a weekend getaway or a special event, it offers stunning views of the Capitol from the Room with a View on the top floor. The home is ideal for entertaining with large dining spaces both inside at the dining room and outside on the large private back patio. Highlights: Spacious Accommodations: Features oversized adult bedrooms (two King rooms, one Queen room) and a fun twin bunk room for kids. Modern Amenities: Upgraded kitchen, 2.5 baths, luxury linens, complimentary starter amenities, and boutique-level service. Outdoor Space: Private fenced patio with dining for 6 and a grill. Indoor Dining: Formal dining room table for 8 Location, Location, Location: Step out of the house, stroll through a charming alley (perfect for social media snaps!), and find yourself on bustling Main Street. Dine at local restaurants, shop unique boutiques, and soak up Annapolis’s vibrant waterfront scene. Just four blocks from the U.S. Naval Academy and a short drive to Washington, DC, or Baltimore, it’s ideal for exploring the area. Parking: No on-site parking. One dedicated space is provided in a nearby garage (10-minute walk). The garage charges a one-time $5 per vehicle service fee. Please contact us for parking details. Sleeping Arrangements (Sleeps 8): King Suite (2nd Floor): King bed, en-suite luxury shower King Guest Room (2nd Floor): King bed, shared full bath Bunk Room (2nd Floor): Two twin beds, shared full bath Room with a View (3rd Floor): Queen bed, skylight with Capitol views, shared 2nd-floor bath Additional Features: Flatscreen TV and high-speed WiFi Washer & dryer Dedicated garage parking (0.7 miles away). Keyless entry with electronic lock. Distances: U.S. Naval Academy: 4 blocks. Annapolis Waterfront: At the end of Main Street. Washington, DC: 30 miles. Baltimore: 25 miles. House Rules: Must be 25+ to book; no parties, smoking, or pets. Quiet hours apply – please respect our neighbors. Check-in: 4:00 PM | Check-out: 11:00 AM. Don’t miss out on this charming retreat—perfect for family getaways, Naval Academy events, or enjoying all that Annapolis has to offer! **Parking is not on premises!! A dedicated parking spot at nearby garage (10/15-minute walk) is provided. Please contact us for details. 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 STR21-144968

Stroll to Main St & USNA w Capital Views & Parking

This beautiful and cozy 3-bedroom, 2.5 bath home built in 1900 is located on Prince George Street, one block from Annapolis City Dock and Gate 1 (main gate) of the US Naval Academy. Filled with sunlit, spacious rooms and equipped with numerous amenities (incl. gas fireplace), this home can sleep up to 8 (on 4 beds in the 3 bedrooms and 1 futon in a private room in the basement) and offers a combination of location and charm that is hard to beat! The space This home has 3 spacious bedrooms that feature 2 queens, 2 twins, and a rollaway bed. There is also a private room in the basement equipped with a futon. The living room has a fully functional gas fireplace - perfect for staying cozy in the colder months. There is a newly renovated, fully equipped kitchen, complete with cookware, basic spices and oils, Keurig coffee maker (with complementary K-cups), and blender. The back patio offers a sitting and eating area as well as a grill for cooking outdoors, and the front porch, which faces attractive Prince George Street, is the ideal place for your morning coffee. Washer and dryer are available to guests as are two smart TVs, both set up with YouTube TV. The top floor offers a secluded working space and reading nook with a partial view of downtown Annapolis and the dome of the USNA Chapel — perfect for those looking for a quiet spot. Guest access Smart Lock keypad for easy and contactless entry

Historic & sunny home steps from USNA/downtown

Walk to Navy-Marine Corps Memorial Stadium from this 2,400 sq ft renovated home with a finished 930 sq ft basement. Chef's kitchen with GE Café appliances and quartz island, master suite with spa-like marble bath, and a basement with full bath, laundry, and extra sleeping. Three bedrooms, 3.5 baths - ideal for game-day groups, USNA families, or Annapolis weekends. The space The main level flows from a welcoming entryway seating area into the open-concept kitchen and living space. Just off the kitchen, an enclosed living room with a sectional and TV provides a quieter hangout spot. The chef's kitchen is the centerpiece: GE Café appliances, a large quartz island with seating, white shaker cabinetry, and coastal clam shell chandeliers that set a warm tone for the whole floor. Upstairs, the master suite has soaring ceilings, a spa-like marble bathroom with a 72-inch double vanity, and a desk nook for remote work. Two additional queen bedrooms share the second floor, each with its own closet and quality linens. The finished 930 sq ft basement adds a full bathroom, laundry, additional sleeping, and a flexible space for games, movies, or overflow guests. With 3.5 baths total, morning bottlenecks aren't an issue even with 10 people. Guest access Guests will have access to the home by keypad entry. The code changes with every guest. Other things to note 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. Pets allowed after paying the pet fee ($100 each) - maximum 50 lbs, 2 pets. Exceptions are made on special request. **Early Check-In & Late Check-Out Policy** We offer early check-in and late check-out upon request, subject to availability. One hour is complimentary However, a fee applies as follows: 	•	Early Check-In before 3pm for an additional fee of $50 to be paid before check -in 	•	Late Check-Out after 12pm for an additional fee of $50 to be paid before check-out Please request in advance so we can confirm availability. Thank you! The dock shown in the photos is a neighborhood dock shared with other residents and is not private to the home

Stadium-Side Annapolis | Chef Kitchen | Sleeps 10

Townhome Steps to Capitol Bldg Backyard & Parking

Recently Updated Home on the Eastport Peninsula with all new Furniture! A Short Walk to dozens of restaurants and shops! Perfect for entertaining - Has Plenty of Off-Street Parking and large Fenced in Private Back Yard with a Wood burning Fireplace! 2nd Floor Balcony great for Coffee Time or Happy Hour SLEEPS 6-10! Has 3 Dedicated Bedrooms, but the Office Upstairs comes with a Queen Air mattress, and the Master Bedroom is enormous - plenty of space for a 2nd Queen Air mattress (Provided). The space Spacious Family Room with Gas Burning Fireplace - Plenty of seating in the Dining Room and Kitchen Area! Covered Balcony outside 2 Desk Office for Hot Nights! Plenty of Closet and Drawer Space in the Bedrooms, with a Full Size Washer/Drier! Guest access Guest has access to the entire property, except the Attic and Shed. There are a Handful of Cabinets locked for Owners storage, but plenty of room left available. This house was bought and designed to be a AirBnB!

Updated Eastport Gem with Outdoor Fireplace!!

Welcome home to this Annapolis gem. An adorable 1930 American foursquare with private driveway, located on a quiet cul-de-sac off in downtowns Art's District. This cozy, three bedroom home can hold you and nine guests with plenty of sleeping arrangements for everyone. Enjoy a spacious backyard patio with string lights and deck chairs giving you and your guests plenty outdoor entertaining options. This house is fully furnished. Short walk to everything downtown offers, it just needs you! The space This house is the perfect mix of “close to it all” and “quiet, cozy respite.” Nicely nestled off a cul-de-sac with off street parking, fenced-in backyard and outdoor patio. Great find in Annapolis’s President’s Hill neighborhood. Come in the spring to see Main Street open up for outdoor dining. Stay in the summer for all the city’s waterfront has to offer. Visit on a fall weekend to catch Navy on the gridiron. This house is the perfect stay for all things Annapolis. 15-20 minute walk to the Naval Academy (0.9 Miles) through historic downtown Annapolis (though it may take you longer since the many shops and restaurants along the way may entice you to linger) We are pet-friendly on a case-by-case basis (Pet fee will apply). Please include information on booking if you are thinking about bringing your pet. If you bring your pet, you are responsible for all aspects of your pet, including cleaning up after them in the yard. The house is 3 stories plus a lower level. Sleeps 6 in standard beds with room for 4 more utilizing the pullout sofa in the living room and the Murphy bed in the lower level. 1st Floor: Kitchen Dining Room Half Bath Living room with queen sleeper sofa 2nd Floor: Full Bath with Clawfoot tub 1st Bedroom has a king bed 2nd Bedroom has a queen bed 3rd Floor: Queen Bed and ensuite full bath with shower Lower level: Murphy bed (queen size) Desk Laundry room Guest access You’ll have full access to the house. Take advantage of the grill out back to cook up some burgers and hot dogs when the weather is nice. Back gate offers immediate access to the West Street restaurants. Other things to note There is a private driveway for that can fit 2, possibly 3 smaller cars. Parking for this property is limited to what you can fit in the driveway (street parking is limited to full time residents with a permit). If bringing more cars than that, we can directed to a nearby parking garage with nightly rates.

Charming Downtwn Home- Private Parking Patio&Yard!

Experience the Difference: Professionally Managed by iTrip Annapolis The space Stay right in the heart of Historic Annapolis, just 2 blocks from Main Street. This 2-unit property offers the opportunity to stay together while each having your own apartment. The Historic building, once a grocery store and the residences of the store, is the perfect blend of convenience and comfort in the two well-appointed spaces, each with their own full kitchen, bedrooms and bathroom. Main Sail on the main floor: 2 bedroom/1 bath, sleeps 6 The Jib on the 2nd floor: 1 bedroom/1 bath, sleeps 4 Property Highlights: Central Location: Walk to all the attractions of Historic Annapolis, including Main Street, just 2 blocks away, and the U.S. Naval Academy, another 2 blocks away. Sleeping Arrangements : Main Sail, main floor (Sleeps 6) King Bedroom: King Bed, Full-size Sleeper Sofa (linens provided) TV Queen Bed Shared Bathroom: Full bath in the hall with stand-up shower The Jib, 2nd floor (sleeps 4) King Bedroom: King Bed Twin futon (plus 2 more Twin futons in the closet; linens provided) Full Bathroom in the hall with combo bathub/shower Additional Features: Modern Amenities: High-speed internet and WiFi, two flat-screen TVs Dining: Full kitchens with seating for 4-6 guests in each unit Luxury Linens: Luxury bed and bath linens, complimentary toiletries Starter Kit, and boutique-level service Convenience: 2 Full-size washer and dryers - one in the 1st floor unit, the 2nd in the main entrance of the 2nd unit Easy Access: Keyless entry; Walk into the building's lower level then up to the 2nd floor where there will be a lockbox on the wall with the key to the unit. Convenient Parking: Parking for one car on driveway behind home Dog-Friendly - available after payment of $150 per dog is made prior to checkin Property Distance to: Main Street: 2 blocks U.S. Naval Academy: 4 blocks Washington, DC: 32 miles Baltimore: 31 miles Amenity & Supplies Starter Pack: Included: A starter set of coffees, sweeteners, soap, shampoo, conditioner, lotion, hand sanitizer, paper towels, toilet paper, dish soap, sponge, and dishwashing liquid Fresh Linens: All beds are made with freshly-laundered sheets, and towels are provided in the baths. House Rules: Age Requirement: At least one member of the party must be 25 years of age. No Smoking Respect: Be respectful of the house, contents, neighbors, and neighborhood. No parties. Check-in/Check-out: Check-in time is 4:00 pm, and check-out time is 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 015881_2025

Two-Suite Historic Home Steps to Main St w Parking

Our 1700s home offers a perfect blend of luxury and comfort. With three beautiful bedrooms, three bathrooms, and a sleek lounge area, it’s a perfect place to relax and unwind. The fully stacked kitchen is ready and waiting for you to cook a perfect meal and enjoy a glass of wine. The location is ideal, with the US Naval Academy just a 5-minute walk away. If you are looking for a peaceful escape or a fun vacation, our property has something for everyone. ✔ King Beds ✔ Smart TVs ✔ Sport Equipment The space Welcome to Villa Annapolitana (STR22-145123)! As you step through the door, you'll be greeted by a warm and inviting atmosphere, complete with comfortable furnishings, luxury decor, and all the amenities you need for a relaxing and enjoyable stay. Whether you're here for a romantic getaway, a family vacation, or a business trip, our property has everything you need to feel right at home. From the grand bedrooms to the spacious living areas, our property has been carefully designed to provide you with a comfortable and memorable stay. Enjoy a good night's sleep in our plush beds, relax in the modern lounge area, or prepare a delicious meal in our fully equipped kitchen. Also, with so many top attractions and delicious restaurants nearby, you'll never run out of things to see and do in Annapolis. Book your stay at our property today and start creating memories that will last a lifetime! ✔ King Sized Beds ✔ Modern Decor ✔ New Appliances ✔ Fresh Towels & Linens ✔ 5☆ Resort Comforts ❖ LIVING ROOM ❖ Coming into our sleek living room, you'll be greeted by a grand and inviting atmosphere that will make you feel right at home. You'll first notice the expansive sofa opposite a stunning wall-mounted smart TV and a warm fireplace, perfect for snuggling up and watching your favorite movie, sports game, or TV show. There's also a single chair placed next to the fireplace, providing ample seating for everyone. If you need a quiet space to unwind or catch up on reading, you'll love the two velvet chairs in the corner of the room, accompanied by a charming small table with a chess board on top. The plush velvet chairs offer a comfortable and intimate space to relax and enjoy a cup of tea or engage in a friendly chess game or board game with loved ones. ✔ Plush Sofas & Chairs ✔ Smart HDTV ✔ Natural Light ✔ Chess & Board Games ❖️ KITCHEN & DINING ❖ As you enter our open-plan kitchen and dining area, a warm and inviting atmosphere beckons you to indulge in a sensory experience. Beautiful wooden units are paired with sleek stainless-steel appliances, including a large refrigerator, cooker, oven, microwave, and dishwasher, while multiple coffee makers offer the perfect start to your day. With ample worktop space, you can unleash your inner chef and create culinary masterpieces before settling down at the modern dining table, complete with four fitting chairs, or take your delicious breakfast onto the breakfast bar, ready and waiting for you with 2 comfortable stools. A carefully selected vintage-inspired bar tool set will let you mix up bar-quality cocktails and take your mixology skills to the next level. And if you're craving some fresh air, the dining area provides direct access to the two large windows opening in the back of the house, perfect for soaking up the sunshine and relishing in the beautiful surroundings. ✔ Microwave ✔ Gas Stove ✔ Coffee Maker ✔ Nespresso ✔ French Press ✔ Bialetti ✔ Oven ✔ Dishwasher ✔ Wine, Champaign & Cocktail Glasses ✔ Dinnerware set for 8 ✔ Vintage Cocktail Set ✔ Toaster ✔ Blender ✔ Fridge ✔ Freezer ✔ Sink - Hot & Cold Water ✔ Silverware ✔ Pots & Pans ✔ Garbage Disposal ✔ Dining Table with Seating for 4-6 ✔ Breakfast Bar with 2 Bar Stools ❖️ SLEEPING ARRANGEMENTS ❖ Welcome to the master bedroom, greeted by a regal king-sized bed covered in luxurious linens and plump pillows. The room boasts a high vaulted ceiling, which creates a relaxing atmosphere, especially when combined with the warm fireplace at the foot of the bed. Two stylish wooden chairs bask in the natural light that floods the room, and ample storage space is available for your belongings. Connected to the master bedroom, bedroom number 2 awaits you with a serene queen-sized bed and wall-mounted HDTV. The room also features a dedicated workspace, perfect for those who need to attend to work during their stay. Descending to bedroom number 3 in the basement, you'll find another king-sized bed. This one enveloped in plush bedding to ensure a peaceful night's rest. The modern furnishings provide a luxurious feel, while a stylish single chair and small table offer a comfortable spot to curl up with a good book. This bedroom also includes an ensuite bathroom, adding a touch of privacy and extra convenience. We can provide a Baby Crib, a Pack 'n Play, and other baby gear, as well as a twin inflatable mattress upon request. If you need additional blankets or pillows, just ask! ♛ Bedroom 1: King Bed With Fireplace ♛ Bedroom 2: King Bed With En-Suite Full Bathroom ♛ Bedroom 3: Additional Bedroom With Queen Bed, HDTV, and Dedicated Workspace The bedrooms are equipped with the following amenities. ✔ Premium Pillows, Linens, and Sheets ✔ Decoration and Comforts ✔ Room-darkening shades ❖️ BATHROOMS ❖ Moving onto the bathrooms, located upstairs and accessible from bedrooms number 1 and 3, you'll be greeted by a spacious, fully-tiled walk-in shower that's perfect for unwinding and relaxing after a long day. The vanity area provides ample room for getting ready, while natural light from the window and skylight floods the space, adding to its serene atmosphere. The second bathroom, situated in the basement as an ensuite, features a stunning walk-in shower and a large mirror for primping and prepping. With its chic gold accents and modern decor, the bathroom perfectly complements the bedroom's luxurious furnishings. It's the ideal spot to indulge in a revitalizing shower and wash away all the stresses of the day Last but not least, just off the living room area you will find a small stylish half bathroom with a toilet and sink. ✔ Shower ✔ Vanity ✔ Mirrors ✔ Toilet ✔ Essential Toiletries ✔ Cleaning Products ❖ BASEMENT LIVING ROOM ❖ Descend into the basement lounge and you'll be greeted by a delightful seating area with two plush chairs, inviting you to sink in and relax. This intimate space is perfect for a quiet chat or sharing a glass of wine with your loved ones. And for those fitness enthusiasts, you'll find some basic gym equipment available to help you maintain your routine while you're away. ✔ Basic Gym Equipment ✔ Comfortable Seating for 2 ❖ LAUNDRY ❖ Our laundry area provides easy access to the washer and dryer, ensuring that you won't have to worry about dirty clothes during your stay. Whether you need to wash a few items or do a full load, our laundry facilities are designed to make the process as easy and convenient as possible. With everything you need right at your fingertips, you can focus on enjoying your trip without having to worry about laundry. ✔ Washer ✔ Dryer ❖️ ADDITIONAL FEATURES ❖ ✔ Wifi ✔ TV ✔ Hair dryer ✔ Washing machine ✔ Dryer ✔ Iron ✔ Board games ✔ Ceiling fan ✔ Heating ✔ Smoke alarm ✔ Carbon monoxide alarm ✔ Fire extinguisher ✔ First aid kit ✔ Dedicated workspace Guest access The entire space is available for you, except for the adjacent backyard, which does not belong to the property.

Villa Annapolitana • Parking 1 min • USNA 4 min

Sun-drenched downtown apartment with huge balcony, less than a block from the water and stunning views from every window. Recently renovated and thoughtfully styled! Sleeps 8 with 2 bathrooms, an open-concept living room/kitchen, and a full dining room. In the shared parterre garden, relax in Adirondack chairs overlooking picturesque Market Street. Peaceful yet walkable to all downtown spots in <10 minutes.

The Sail Loft

Waterfront guesthouse in gated community on a creek off of the Severn River with clubhouse, swimming beach, tennis court. Approximately five miles from downtown Annapolis. NO PETS, NO SMOKING, NO PARTIES. Parking for up to four cars only. Anne Arundel County License Number STR-120. The space Fish from pier (~5 ft depth at end of pier), double kayak and single pedal-paddle boat available. Table tennis in basement. Owners live next door. ~ 6.8 miles to City Dock by car; ~ 2 miles by boat. Other things to note Queen air mattress and sleeping bag also available. Access to washer and dryer if staying for three nights or more.

Quiet Waterfront

Relax and unwind in the heart of Annapolis! This well-appointed home is centrally located in the prestigious Murray Hill neighborhood - one block from Annapolis Hall and popular restaurants, a few blocks to Spa Creek where you can drop our two kayaks, an easy walk to Navy Marine Corps Stadium and about a 20 minute stroll to downtown. Experience Annapolis' boating, shopping and culinary scene or relax on the spacious deck around the fire pit, utilizing our gourmet kitchen! The space This property is on one level for easy handicap access. There is a drive for off street parking and a shed that holds four bikes and two kayaks for your use. The end portion of the house can be separated by a sliding door, with access to the third bedroom and bath as well as a kitchenette for privacy. It has its own entrance! Other things to note Lots of extras for your use during stay - bikes/helmets, kayaks, cooler, umbrellas, beach towels, games and books. Great place to entertain with a gourmet kitchen and so many lovely serving pieces and glassware. The dining table accommodates eight people and there’s additional seating for four at a bar and three at the island. Enough matching dinnerware, utensils and glassware - including wine, water, champagne, beer and martini - to serve all! Also pretty plasticware for outdoor dining!

Nautical - 
and SO nice!
Park Free
Walk to Stadium

A driveway adjacent to the house with free parking for 2-3 vehicles is a bonus to this charming, newly renovated home in downtown Annapolis. This property is located on Prince George Street steps away from downtown shops and restaurants and is a quick walk to St. John’s College and the USNA. Nautically themed with a touch of historic charm, the house features comfortable rooms filled with natural light, high-end finishes, and a lovely front porch with rockers to relax and enjoy the neighborhood. The space This newly renovated home in downtown Annapolis on Prince George Street boasts modern elegance with a touch of historic charm. Featuring spacious rooms filled with natural light, high-end finishes, and state-of-the-art appliances, it offers a perfect blend of contemporary comfort and classic architecture. The prime location allows residents to enjoy the vibrant atmosphere of downtown Annapolis, with shops, restaurants, and cultural attractions just steps away. Other things to note Downtown Annapolis captivates with its picturesque charm and rich historical ambiance. Cobblestone streets wind through a landscape adorned with colonial architecture, where quaint shops and inviting cafes line the sidewalks. The iconic State House stands proudly, overlooking the scenic waterfront of the Chesapeake Bay. Visitors can explore maritime history at the Naval Academy, savor seafood delicacies, and soak in the nautical allure of Ego Alley, where boats dock along the charming harbor. Downtown Annapolis exudes a timeless appeal, inviting both residents and tourists to immerse themselves in its unique blend of history, culture, and maritime beauty.

The Midship Quarters

Welcome to your home away from home at the Naval Nook! ~ 4 min. Uber from Downtown Annapolis ~ Brand New Hot Tub ~ Cool Electric AC ~ King Bed ~ Sunroom with Daybed and Trundle ~ Zero Gravity Chairs ~ Outdoor Dining table ~ Beautiful Spacious & Comfortable bedrooms ~ Couch w/ Queen Bed pullout ~ 4 Smart TVs in each bedroom & living room ~ Tiled showers w/ shampoo & conditioner ~ Fully equipped kitchen ~ Luxurious Linens ~ Luxury Electric Fireplace Airbnb Registration #: STR23-145225 The space When you walk in, just take some time to explore your awesome temporary home. You can see almost the entire space from the entrance of the house besides beds and baths! The extremely spacious yet comfortable living room is perfect for staying warm and cozy after spending the day outside. Guest access You'll be able to access the full space except for the crawl space downstairs from the sunroom. Other things to note Please watch your step in the following areas, there are small steps up/down here and there: ~As you enter the living room ~The master bedroom Please, keep the master bedroom door closed before you sleep. There is an automatic light that may turn on if you move around in the bedroom.

The Naval Nook 1.3 mi. from Downtown Annapolis

Experience the Difference: Professionally Managed by iTrip Annapolis The space When the owners decided to find their Annapolis home base, they knew they had to be within walking distance to the one’s USNA alma mater. What they found with this special home is so much more! This historic home's family room off the kitchen has the most stunning decorative fireplace dating back to 1730. It was the meeting place of the 18th century social "Tuesday Club" that is rumored to have hosted Benjamin Franklin. This centrally-located home is three blocks to City Dock, a block from Gates 1 and 3, and a block from charming Maryland Avenue's shops and restaurants. *Parking: No on-site parking. One dedicated space is provided in a nearby garage (10-minute walk). The garage charges a one-time $5 per vehicle service fee. Please contact us for parking details. The main floor is welcoming and spacious while all newly-decorated to host your family gathering. Walk through the bright entry hallway or formal living room with ample seating to the dining room, with decorative fireplace and seating for 8. The light and airy kitchen with custom tile has a Viking stove, stainless side-by-side refrigerator with water dispenser, dishwasher, breakfast table for 2 and large pantry. Adjacent to the kitchen is a laundry room with half bathroom and cozy family room. The brick family room features comfortable seating, another decorative fireplace, and a 65” flat screen smart TV to enjoy football games. Head out the back door to the beautiful brick patio with an outdoor dining table for 6. The back patio also includes a gas BBQ, fire pit, Adirondack chairs for 4, and plenty of room to grill, relax and enjoy breathtaking views of the newly-renovated Naval Academy Chapel dome. From the bottom level, head upstairs along the hand carved mahogany banister to the 2nd floor with 2 bedrooms and 2 full baths (shower tub combination and shower stall). Master bedroom has a King bed and 55” flat screen smart TV with en-suite office. Guest bedroom has a Queen bed. Both rooms share a large walk-through closet. Upstairs from these 2 bedrooms, on the 3rd floor, is the carpeted attic bedroom with 2 Full and Twin beds (sleeping 3 upstairs), bench window seating, and skylights with views of the Chapel dome. SLEEPING ARRANGEMENTS 3 BR / 2.5 BA / Sleeps 7: King Bedroom: - Second Floor - King Bed - Adjoining deck space and walk-in closet Queen Bedroom: - Second Floor - Queen Bed - Adjoining walk-in closet to King Bedroom 3rd Floor Guest Bedroom: -Third Floor -2 Full Beds -Twin bed HIGHLIGHTS: - Beautiful new gourmet Kitchen with custom tile, Viking range and wine fridge - Large back brick patio with outdoor dining table for 6 - Outdoor Firepit with seating for 4 - Eat-in kitchen table seats 2 - Dining room table seats 8 - BBQ Grill (propane included) - WiFi - Big Screen Smart TV's - Luxury linens, complimentary toiletries Starter Kit, and boutique-level service - Washer & dryer located inside the home - Elderly and guests with mobility issues may want to inquire about the steep staircase and/or may want to consider other accommodations. - Keyless entry. Drive straight to your rental home and enter the electronic lock code on the front door. Property Distance to: - U.S. Naval Academy – 1 block - Washington, DC – 30 miles - Baltimore - 25 miles * Amenity & Supplies starter pack, coffee and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going. * All beds are ready made for you with freshly laundered sheets & towels. House Rules Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking/no pets. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind. Check-in time: 4:00 pm Check-out time: 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 STR21-145005

Views of USNA Chapel, Walk to Gate 1 w Parking

Welcome to The 1845 Outpost, a comfortable, well-equipped home in the heart of Annapolis. Built in 1845, the same year the U.S. Naval Academy opened its doors, this outpost has been a steadfast neighbor and witness to history. Home to two USNA graduates, Classes of 1993 and 2024, this house has been an outpost of sorts for countless Mids in search of a relaxing respite from the rigors of school. We hope you enjoy it and make some memories during your stay.

The 1845 Outpost

Welcome to 17 Lafayette Ave—your charming retreat in the heart of historic Annapolis! Just steps from downtown, the U.S. Naval Academy, shops, and waterfront dining. This cozy home blends modern comfort with historic charm, featuring a full kitchen, fast Wi-Fi, and private outdoor space. Perfect for couples, families, or business travelers looking to explore the best of Annapolis on foot.

Cozy Stay in Downtown Naptown

This fully renovated three bedroom home sleeps 8. A touch of Key West comes to Eastport in this beautiful cottage style home. Beautiful open concept kitchen, dining and family room. Off street parking holds 3-4 cars. The space Experience a cozy retreat in this inviting 3-bedroom, 2-bathroom cottage, just 3 blocks from the historic Spa Creek Bridge in Eastport. Perfect for families or small groups, this home comfortably sleeps 8 and offers the ideal blend of convenience and relaxation. The Space Bedrooms: Master Suite with King Bed & En Suite Bath (walk-in shower, double vanity) Guest Room with Queen Bed Second floor bedroom with 4 Twin Beds (perfect for kids or extra guests) Bathrooms: Master Bathroom with walk-in shower and double vanity Hall Bathroom with tub/shower combo Living Area: Open-plan layout with a spacious family room featuring an L-shaped sectional, a dining table for 8, and a bright, white kitchen. Ideal for gatherings and creating memories. Key Features: Pet-Friendly – bring your furry friends! Off-Street Parking for 3 Cars Spacious Yard for Outdoor Fun Fully Equipped Kitchen for Home-Cooked Meals Located just a short walk to Spa Creek Bridge and local shops, restaurants, and attractions. Whether you're here to explore the charm of Eastport or simply unwind in a comfortable home away from home, this cottage offers the perfect setting for your stay. Guest access The entire house is yours, property manager lives in the area in Eastport and owners lives downtown. So we are there if you need us, but you will have total privacy during your stay.

Charming Renovated Eastport Home

Experience the Difference: Professionally Managed by iTrip Annapolis The space Still available for Commissioning Week 2025! Welcome to this beautifully remodeled Victorian home in Eastport, lovingly named "Around the Corner" for its prime location near Annapolis' best dining, shopping, and waterfront experiences. This 2-story retreat seamlessly blends historic charm with modern conveniences, making it perfect for a memorable getaway. Key Features: Inviting Wrap-Around Porch: Begin or end your day relaxing on this quintessential Eastport feature. Spacious Living & Dining Areas: Heart of pine flooring throughout creates a warm, welcoming atmosphere. Gourmet Kitchen: Fully updated with custom cement countertops, breakfast bar, and wine fridge. Outdoor Oasis: Enjoy a private fenced-in backyard with a furnished patio, lounge chairs, and gas grill. High-End Baths: Luxury fixtures, Restoration Hardware vanities, and boutique-level linens. Sleeping Arrangements (Sleeps 8) Sunny Front King Bedroom: King bed, walk-in closet, and access to a full hall bath. Middle Queen Bedroom: Queen bed with access to the hall bath. Bunk Room: Twin bunk beds and built-in laundry room. Living Room: Queen sleeper sofa with access to the 1st-floor full bath. Amenities to Enhance Your Stay: High-speed Fios internet (1 Gig) & WiFi Flat-screen TV Complimentary coffee & starter toiletries kit Full-sized washer & dryer Luxury linens & boutique-level service Keyless entry Pet-Friendly: Small dogs (50lbs or less) welcome with a $150 non-refundable fee per dog Private driveway (1 car) + unrestricted street parking Location Highlights: Downtown Annapolis: 0.8 miles (3 minutes) U.S. Naval Academy: 1 mile (5 minutes) Washington, DC: 32 miles Baltimore: 30 miles House Rules: Age Requirement: At least one guest must be 25 or older. No smoking No parties or events. Check-in: 4:00 pm | Check-out: 11:00 am Ready to experience historic Eastport with all the comforts of home? Book your stay at Around the Corner and immerse yourself in the beauty and charm of Annapolis! 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 145043

Walk to Eastport Hot Spots w Fenced Yard & Parking

Charming home in Annapolis This centrally located rental is steps away from everything Annapolis offers! Whether you're in town to explore the iconic Naval Academy, catch a game at the stadium, or enjoy a craft brew at the local brewery, you’ll find it all just a short stroll from your door. Indulge in unique dining at one-of-a-kind restaurants or unwind with loved ones at nearby outdoor spots. For those who love the water, bay access is just a block away. Discover Annapolis! The space Master Bedroom: Queen-sized bed and attached full bath Second Bedroom: Queen-sized bed Third Bedroom: Full-sized bed Living Area: Includes a pull out sofa bed for additional sleeping space

Walk to Navy Stadium & Shops. No cleaning fee!

This stunning detached, comfortable, pet-friendly home, designed by Stylish Stays, is the perfect place for a stay in THE HEART of Downtown Annapolis. This highly walkable property is located in the Arts District, w/ close by shops, restaurants, bars, waterfront, State House, and Naval Academy! ☞ 15+ seconds to great restaurants! ☞ 13 min walk to State House ☞ 15 Min walk to Navy-Marine Memorial Stadium ☞ 19 Min walk to City Dock ☞ 35 Min drive to Baltimore ☞ 40 Min drive to DC ☞ Fenced Yard The space Enjoy your stay with us! This space offers: ☞ Professionally Designed, Furnished, and Appointed ☞ 3 Bedrooms Comfortably Sleeping 8 (1 King, 1 Queen, 1 Full Murphy Bed, 1 Queen Sofa Bed) ☞ 2 Full Baths w/ 1 bathtub and 1 shower ☞ High Quality Helix mattresses for a restful night's sleep ☞ Fully appointed Kitchen with electric range and convection oven, full sized microwave/dishwasher/fridge, plenty of counter and cabinet space laid out for entertaining and hosting ☞ Deck off second bedroom, Brick Patio, and fenced yard w/ full outdoor dining set and Adirondacks so you can truly set off the vibes ☞ Black out curtains in each bedroom when you want it darker ☞ 2 Story Entry Foyer for a spacious airy feel ☞ Dedicated work area with second monitor ☞ Reliable FAST Internet Connection (300mbps) ☞ Smart TVs in every living space w/ Apple TV and Chromecast ☞ Reliable WIFI throughout the home ☞ Full Sized Laundry in unit ☞ Fully Stocked Bathrooms w/ Paya brand bath amenities ☞ Nearby Restaurants/Shops/Historical Sites/Bars/Music Venues/Markets/Parks ☞ EZ Baltimore/DC/BWI Location ☞ Mellow lighting throughout ☞ High quality sheets and towels ☞ Quiet and comfort Inside, yet Vibrant City Life outside the door Here are some of our Past Guest comments from other properties we host: "Terrific host - very helpful and communicative." - Kelly "The host was communicative and accommodating. Would definitely stay here again!" - Ayla ☆☆BEDROOMS☆☆ This well thought out detached home accommodates 8 guests in 3 bedrooms. The stylish primary bedroom is on the first level and is fitted with a king-size bed w/ Helix Midnight Mattress, a closet for clothing storage, and door to rear brick patio living space. The second bedroom has a queen-size bed, closet, and door to rear deck overlooking the fenced yard. The third bedroom has a Full sized murphy bed w/ Helix mattress, large closet, and a full sized desk and chair with full sized monitor. Each bedroom has an individual ductless HVAC unit to control the climate for that room, and TV The Living Room has a sofa that converts to a queen sized pull out bed with memory foam mattress ☆☆BATHROOMS☆☆ There are two full and bathrooms in this home, each stocked with all the essentials you need for your stay. The first level bathroom has a walk-in shower, and the full sized washer/dryer units. The second full bathroom is on the second level off the living room and has a shower/tub combo. ☆☆KITCHEN AND DINING☆☆ The combined kitchen and dining area was designed for serious cooking and entertaining! Fully equipped with all appliances, utensils, cookware, and glassware you will feel right at home. With a 4-burner glass cooktop, convection oven, microwave, full sized dishwasher and refrigerator, you will thank yourself for staying with us so you have the ability to make a full Thanksgiving meal if you wanted to! There is total dining seating for 8, multiple coffee making options, and full cocktail making equipment! ☆☆OUTDOOR SPACE☆☆ There is a large brick patio with 8 person dining table, outdoor sofa, and Adirondack chairs offering ample seating options. Enjoy the night sky in this fully fenced yard. The remainder of the yard is rubber mulch ☆☆LOCATION☆☆ Annapolis is known for being one of the oldest and most storied state capitols in the country. The surrounding neighborhoods are picturesque with historically designated homes and businesses. You are a 5 min drive from EVERYTHING Annapolis has to offer, but where this property really shines is it’s ease of walkability to everywhere. There are great restaurants starting literally 2 doors down from us! ☆☆Guest Agreement☆☆ For any bookings of 30 days or more, the guest will be required to sign a Guest Agreement. A copy of this agreement will be provided. For stays over 30 nights, we include monthly spot cleaning and the first $350 of internet, electricity, and water utilities. Any overages will be due from Guest. More frequent cleanings, refills and full cleanings are available at an additional fee, which will be determined later, including the mode of payment. Guest access Self-check in w/ digital locks. BE SURE TO READ PARKING INSTRUCTIONS FIRST Other things to note **PETS** • There will be an additional cleaning fee • Your pet will have to be crated if no adults are home • Guests will be responsible for all damage, noise, and messes • Guests must pick up all pet waste and properly dispose of it, while being respectful of neighbors' yards and property • Poop bags should go into specified poop trash can (no loose poop bags in the large trash bins, please) • Pets aren't allowed on the sofas/chairs/benches. They ARE allowed in beds as we can more easily clean the sheets • Pets shouldn't be left unattended outside These rules are intended to prevent any issues with pets. Ultimately as long as there are no issues in the house from any pets, we will assume our rules were observed **PARKING** • PLEASE NOTE PARKING IS NOT INCLUDED WITH THIS PROPERTY. • There are three nearby pay parking garages that are a 2 and 5 mins walk, 2 hour adjacent neighborhood parking, and nearby alley (Ellington Alley) for loading/unloading • As of April 2024, Overnight garage parking rates are $23 and $10 respectively, depending on the garage you park in • Side streets have a 2-hour parking limit. For more parking details, please refer to the Parking section in our House Manual. Rental Registration number #STR23-145297

Stylish & New | Pet Friendly | Walkable Downtown

Welcome to our elegant stand alone charming home on Charles Street in Historic Annapolis. This 3 bedroom 2.5 bath is just a short stroll from Main Street , USNA , Yacht Clubs and Event venues. Plenty of room to relax with a large private outdoor space. The space Stately 3 bed 2.5 bath stand alone home in the Historic District . Guest access Guests have full use of the home Other things to note The city does not allow street parking for short term rentals . Our guests use of the numerous city garages - The closest is one block away . Fireplaces are for decorative use only.

Charming on Charles Street

Situated in the heart of the treasured Historic District of Downtown Annapolis, this home, circa 1762, is on one of the most desirable streets in the Historic District. Originally part of the neighboring Upton Scott house with ties to Francis Scott Key (author of the "Star-Spangled Banner"), the house excuses a sense of character and history with its antique furnishings and original hardwoods. Its unique architectural details and updated comforts create a cozy ambiance. The space This home has tons of character. You will fall in love with cozy interiors, antique furnishings and unique architectural details. On the main level you will find a chef's kitchen with Subzero and Viking appliances, a Miele built-in coffee system, breakfast table seating, a 54" HD Smart TV with an oversized leather sectional sofa, a workspace desk with a printer and supplies. The kitchen is well-equipped for all your cooking needs (cookware, bakeware, dinnerware, including a new knife block set, an air fryer, a smokeless grill, a blender, hand mixer, waffler maker, spices, etc). For those who prefer the ease-of-use approach for coffee there is a Keurig coffee maker with complementary K-cups and an Italian Illy espresso coffee machine with complementary Illy capsules. A workspace desk in the kitchen area is stocked with supplies and a Brother printer. Also on the main level is a separate, generously sized formal dining room with seating for up to 6. The separate main living room offers additional seating and a 43" HD Smart TV over a wood-burning fireplace. The main level powder room and stackable washer and dryer are conveniently located near the kitchen. All cleaning supplies fully stocked. Upstairs there are 3 bedrooms and 2 full bathrooms. The primary bedroom has a 19th-Century drop front Secretary Desk, a 50" HD Smart TV, and an en-suite bathroom complete with its own soaking tub and walk-in shower. The hall bathroom that services the other two bedrooms has an antique claw-footed tub with a shower. All the bedrooms have their own window treatments for light filtering, extra linens, blankets and pillows. In the rear bedroom closet there is a new Ingenuity Dream Retreat 3-in-1 Portable Bassinet & Playard for guests' use. The private back area offers a seating and eating area with a fire pit, perfect for making S'mores (marshmallow metal roasting sticks available for guests' use) and staying cozy during the colder months. Guest access All parts of the home are available for guest use with the exception of the locked basement cellar. Guests will gain access to the home with a lockbox combination code. The lockbox is located next to the front door.

Historic Home in Annapolis

Your family will be close to everything when you stay at this centrally-located place.  Two blocks from, the Naval Academy, Downtown Annapolis and Historic Maryland Ave, this 1875 home has been fully renovated and updated for our guests. Boasting beautiful views of  Historic Paca House and book ended by Spa Creek and St. John's College, the location is amazing.

The Page House

This lovely home has 3 bedrooms, 3 bathrooms, fully equipped kitchen with large island that seats 4 and an outdoor patio featuring a 8 person fire-pit dining table and lounge seating. Gather around our dining room table for family meals, or enjoy the large, privately fenced bricked patio for a cook-out, brunch or cocktail after a day of exploring the town. If you don't feel like cooking, you can take stroll or quick ride share trip to one of the many renowned local eateries in the area. The space As soon as you enter this beautiful two-floor home, you'll be greeted by the modern yet very comfortable open-concept design living area. The fully equipped kitchen combines with the dining area, where you'll cook and enjoy tasty meals with your friends and family. Love to cook seafood? Then you will love the seafood pot and tools that we have in the kitchen for you to use! After dinner, relax in the living room, or head to the outdoor seating area to enjoy the unforgettable Annapolis evenings. Where you will sleep: Each bedroom is designed for comfort and is equipped with a ceiling fan and cozy pillows and bedding. Located on the second floor, the spacious master bedroom upstairs with a king bed, two closets, desk, and en suite full bathroom with shower. The second bedroom to the left of the master bedroom has a queen-size bed. The third bedroom has a queen size bed and full size trundle bed. The living room comes with a very comfortable, queen pullout sofa bed to accommodate all guests. This quiet community is conveniently located less than 4 miles from the Naval Academy and 2 miles from Annapolis Town Center. STR- 145243 Note: 2 pets with a maximum weight of 50 pounds each permitted with a paid pet fee. No pit bulls, American bulldog, rottweilers, akitas, terriers, mastiffs, Dobermans, Great Danes, German Shepherds, huskies, chows, or wolf hybrids are permitted. Guest access The house is exclusively yours, without interruption during your stay, so relax, unwind, and make yourself at home. Other things to note There is plenty of street parking available (no permit required) or you can park in a non-labeled free parking spots.

Belle By The Bay

Beautiful historic home right in the heart of downtown Annapolis. Walkable to USNA and all downtown shops and restaurants. This location cannot be beat! 3 Bedroom, 2.5 bath, quiet outdoor patio, gas grill, and charming kitchen.

Historic Downtown Property

This charming 3-bedroom, 2.5 bath historic duplex in downtown Annapolis offers a perfect blend of timeless character and modern amenities. Featuring hardwood floors, classic architectural details, and an updated kitchen and bathrooms, the home is within walking distance of Annapolis' vibrant waterfront, shops, and restaurants. Enjoy the convenience of city living while embracing the rich history and charm of this well-preserved gem. Ideal for those seeking comfort and style in a prime location. The space Why guests love staying at 215 Prince George Street: ☼ Historic home right in the heart of downtown Annapolis with tons of charm upgraded features, ideal for families, romantic getaways, or a group of friends visiting historic Annapolis, USNA, and other tourist sites ☼ Centrally located in downtown Annapolis, on historic Prince George Street ☼ Three bedrooms: Primary: king bed; Guest 1: 1 queen bed; Guest 2: 2 twin beds ☼ Two and a half bathrooms: Primary suite has a private bathroom with a walk-in shower; hall bathroom has a tub-shower combo; half bath on the main living level ☼ Kitchen with all major appliances, a drip coffee maker, kitchen supplies and tools and more ☼ Comfortable living room for watching movies and playing games ☼ Private outdoor space - fully fenced with outdoor dining and a gas grill ☼ Smart TV in the living room ☼ Fresh linens, towels, toiletries & essentials provided ☼ Professionally cleaned before each visit ​Look no further than this historic home in downtown Annapolis! Please note that there is no assigned parking for this property. Guests are encouraged to park in nearby public parking garages overnight. There is short-term hourly parking on Prince George Street. Please note that parts of this home date back to 1775! So there are some charming quirks that you won't find in new builds, like a low ceiling clearance on the stairs, a step up into the primary suite, a step down and then up in the bedroom hallway, and smaller sinks in some of the bathrooms. It's truly a unique experience! We’ll follow up with a short online registration once you book. It’s fast, simple, and helps us prepare for your visit. Non-Airbnb guests will be asked to pay a small damage waiver OR refundable deposit. For extra flexibility, consider adding trip insurance for a nominal fee. It can cover you if you need to cancel at the last minute. 215 Prince George Street is managed by a small, female-owned business. We're committed to making sure all of our guests feel welcome and have the best trip ever. Book your trip with confidence that not only will this property be amazing, but the service and attention you get will be, too.

Historic Downtown Annapolis Gem Near USNA

Located in the Historic District, our home is a unique blend of vintage charm and modern comforts. Off-street parking in a driveway is a rare find, & additional parking spaces in the rear are available with permission. We are 2 blocks to USNA Gate 1, and 1 mile to the Navy Stadium. A shady and quiet backyard is a peaceful respite, with retail shops, restaurants and coffee houses just steps away. STR# RENT-002617-2025 The space Our home is across the street from the USNA, and sits 2 blocks from the City Dock, Maryland State House, St. John's College, and historic Main Street, and a 15 minute walk to the Navy football stadium! The spacious and light-filled master suite boasts a hotel-worthy spa bathroom featured in Annapolis Interiors Magazine. Second bedroom has a queen bed and the front bedroom has 2 twin beds. An additional full bathroom overlooking the USNA Chapel (with the new copper dome!) completes the upper hallway. Living room couch has a queen pull-out for extra guests. High-end linens and new pillow-top mattresses ensure the luxury of a hotel stay with all the convenience of a quiet home. Private backyard with ample seating, dining set and gas grill, and a front sunroom to watch the world go by offers privacy while still being in the heart of the Historic District. The fully-stocked "cook's kitchen" and open main floor inspires a perfect place to host a small gathering. Available for families, business travelers and small group retreats. Guest access Park in our front driveway, with room for 2 cars! Additional off-street parking for 1 extra car available with owners permission. Lockbox on premises for easy entry - no "check-in" required. (Please do NOT enter the house before the 4PM check in time without prior approval!) Other things to note USNA Commissioning weeks: PLEASE do not put random dates in to inquire. Just send us a simple message and we will get back to you. Base rate for '26 and beyond is $12000 for a minimum 7 night stay for that week. AirBnB fees and taxes not included.

Sophisticated & Spacious Historic Home w/ Parking!

Your family will be close to everything when you stay at this centrally-located home. 3 blocks from the Navy stadium and walking distance to amazing restaurants! Here is your Annapolis home away from home. Our 3 bedroom 2.5 bath bungalow retreat is perfect for 6-7 people wanting to relax and see all that beautiful Annapolis has to offer. There’s also a free shuttle that takes you downtown to the water. Come, enjoy! The space Modern King bed and on-suite Master, Bohemian Queen bedroom shares a full bathroom with the 3rd Country Chic bedroom with 2 twin beds. All bedrooms are upstairs. Powder bathroom, kitchen and living room downstairs. Great deck and grill for entertaining. Large backyard for plenty of yard games. Quiet family neighborhood on a dead end road. Guest access 2 parking spots on the property and plenty of street parking. Walking accessibility to downtown is very easy. Just 1 mile to the middle of Annapolis, restaurants and bars! Other things to note Family friendly home with toys and activities for kids!

The Navy House-Walk or Shuttle Downtown! 3 bd

Private 3 floor house located at the edge of Annapolis historic district. You can be certain that you will have all the comforts you expect here while within walking distance to the navy football field and the navy academy. You can also enjoy all the wonderful food and exciting shopping in between. The house comes with a furnished basement with bathroom/shower. On the first floor, you will find a stocked kitchen with a dining room and living room. Upstairs has 3 bedrooms with a bathroom/bath. The space Welcome to this spacious and fully furnished home, designed to be your comfortable home away from home. Spanning three levels, the layout offers the perfect balance of "together time" on the main floor and "private time" in the finished basement. Whether you are here for a family vacation or a remote-work trip, you’ll find plenty of space to relax and recharge. ✨ Top Features at a Glance ☁️ Premium Sleep: Super comfortable beds with crisp cotton sheets. 📺 Entertainment Hub: Finished basement with a 65” Smart TV. 💻 Remote-Work Ready: Dedicated desk with lamp & comfortable chair. 🏠 Room for Everyone: 3 levels of living space to spread out. 🍳 Chef’s Kitchen: Fully equipped with dishwasher, blender, and coffee maker. 🏠 The Layout Upstairs: Rest & Recharge (3 Bedrooms) We know a good night's sleep is the most important part of your stay. That's why we prioritize super comfortable beds, topped with soft, high-quality cotton sheets, plush pillows, and extra warm blankets. Bedroom 1: Queen Bed Bedroom 2: Queen Bed Bedroom 3: Bunk Bed (Perfect for 2 kids or young adults) Full Bathroom: Features a tub/shower combo, fresh towels, and a toilet with a bidet for added comfort. Main Floor: Gather & Dine The heart of the home! Since there are no bedrooms or baths on this level, it is 100% dedicated to quality time. Living Room: A cozy space to play board games, watch TV, or relax while dinner simmers. Kitchen: A spacious, functional design equipped with a stove, oven, microwave, fridge, and dishwasher. We provide all the pots, pans, and kitchenware you need—plus a blender, water kettle, and coffee maker for your morning routine. Cleaning Essentials: We’ve stocked the pantry with Windex, Clorox, dish soap, and laundry detergent for your convenience. Downstairs: Work & Play (Finished Basement) The ultimate bonus space! Perfect for sending the kids to play or getting some work done in peace. Sleeping: Full-size foldout sleeper couch (Sleeps 2). Entertainment: Massive 65” TV for movie nights. Workspace: A dedicated desk with a lamp, ottoman, and comfy chair. Convenience: Easy access to the downstairs bathroom. Guest access Guests have access to the entire property. This includes a backyard, and all space within the house. Guests will only not have access to the boiler room for safety. If access to boiler room is needed, please contact us immediately. Parking: There is only street parking with enough space typically for one car. It’s a small street for all the houses. But there is also public parking garage that you can use if you have additional cars. Other things to note We want you to know that we’re doing our part to help our Airbnb guests stay safe by cleaning and disinfecting frequently touched surfaces before you check in. We have outdoor cameras that are capable of recording and saving video around the house for your safety.

Annapolis Charm –Bright 3BR in Downtown

This 3-bedroom, 2.5-bath single-family home mixes modern renovations with 1896 classic charm. It's been decorated with upgraded furnishings to accommodate 6 guests. You'll love the proximity to downtown Annapolis. Plus you'll have free parking for up to 3 cars in the private driveway! The space Why guests love staying on Lafayette Ave: ☼ Historic single-family home right in the heart of downtown Annapolis with natural light and upgraded features, ideal for families, romantic getaways, or a group of friends visiting historic Annapolis, Ram's Head On Stage, USNA, and other tourist sites ☼ Centrally located in downtown Annapolis, on historic Lafayette Ave, one block from historic West Street, within walking distance of restaurants, bars, museums, coffee shops, and more ☼ Free parking for up to 3 cars in a private driveway (NOTE: street parking is hard to come by in this neighborhood; Gott's Court Public Garage is about 3 blocks away) ☼ Three bedrooms: Primary: king bed; Guest: 1 queen bed; Guest: 2 twin beds ☼ One full bathroom is on the second level with 3 bedrooms and has a tiled walk-in shower and heated floors; there is a beautiful half-bath on the main living area with heated floors; Another full bathroom is in the basement and has a tub-shower combo (NOTE: the basement full bath is best for kids and shorter adults, as the ceiling heights in the basement are about 5'10"-6-feet tops ☼ Basement has a hangout area with a Smart TV, small couch, and cushions for seating; full bathroom; and laundry (NOTE: Basement can be accessed by a narrow staircase. Basement ceilings are low - so taller adults should watch their heads. We ask that guests do not eat in the basement as to not attract bugs or other pests. This home is kept meticulously cleaned!) ☼ Kitchen with all major appliances, a drip coffee maker, Keurig, kitchen supplies and tools and more ☼ Comfortable living room for watching movies and playing games ☼ Dining room with seating for 6 and an electric fireplace ☼ Smart TV in the living room and basement ☼ Fresh linens, towels, toiletries & essentials provided ☼ Professionally cleaned before each visit ​Look no further than this historic home in downtown Annapolis! We’ll follow up with a short online registration once you book. It’s fast, simple, and helps us prepare for your visit. Non-Airbnb guests will be asked to pay a small damage waiver OR refundable deposit. For extra flexibility, consider adding trip insurance for a nominal fee. It can cover you if you need to cancel at the last minute. Lafayette Ave. is managed by a small, female-owned business. We're committed to making sure all of our guests feel welcome and have the best trip ever. Book your trip with confidence that not only will this property be amazing, but the service and attention you get will be, too.

Renovated Downtown Annapolis w/ 3-Car Parking

Experience the Difference: Professionally Managed by iTrip Annapolis The space Watch the sunrise on the private beach at Oh Happy Bay. The quaint two-story, cottage has a private beach on historic Bembe Beach with direct access to safe, shallow water for swimming, paddle boarding, and boating (small boat mooring). Commissioning Week families will be spoiled by the direct line of sight for the Blue Angels air show. The home is ideal for a large extended family traveling together. Enter the home into the beautifully-renovated kitchen with all new appliances and an adjoining dining room with water views and seating for 6-8. The main floor has a guest room with a Queen bed and full bath with a stand-up shower in the hall. The family room is equipped with a Full-size sleeper sofa. Head outside to the private backyard, with a deck, screened-in gazebo, lounge chairs and a picnic table for outdoor dining, cocktails or morning coffee (sampler starter pack included in your stay). Head back inside and up the stairs to the large family suite with 2 bedrooms, a connecting full bath (with 2 entrances), a sitting room and access to the private 2nd floor balcony. The main bedroom has a King bed and sitting area large enough for a portable crib or air mattress. Across the hall is the guest room with the full bed. The shared bath has 2 vanities, a stand-up shower and soaking tub. Also in the hall is the full-size washer and dryer. The home has plenty of parking and space to explore with the pups and little family members. Located walking distance to Annapolis Sailing School and Capital SUP (Paddleboard lessons and rentals), the Eastport Water Taxi (with water access to downtown Annapolis). Annapolis Maritime Museum and Quiet Waters Park are just a short drive away. SLEEPING ARRANGEMENTS 3 BR / 2 BA / Sleeps 8 adults: Upstairs Waterfront Bedroom: -King bed -Sitting room -Waterfront balcony -Queen air mattress available in the closet -Shared bathroom with stand-up shower and soaking tub -Flatscreen TV Guest Bedroom across the hall from King Bedroom: -Full bed -Shared bathroom with stand-up shower and soaking tub Main Floor Bedroom: -Queen bed -Full hall bath in the hall with stand-up shower Family Room -Full Sleeper Sofa -Full hall bath with stand-up shower HIGHLIGHTS: -Private beach with access to Chesapeake Bay -Screened-in patio gazebo with dining table for 10 -Back deck with seating, picnic table and beachside seating -Charcoal BBQ grill -Gourmet kitchen -Dining room table seats 6-8 -High Speed Internet and WiFi -Big Flatscreen TV -Stand-Up paddle boards, life jackets, beach toys, small boat mooring (this is a mooring ball or permanent anchor system off the beach where small boats can be moored) - Available in the summer months only (May-October) -Luxury linens, complimentary toiletries Starter Kit, and boutique-level service -Outdoor shower -Parking for multiple cars in driveway and on street -Full Laundry room with washer & dryer located inside the home Property Distance to: -Downtown Annapolis – 4 miles -U.S. Naval Academy – 4.5 miles -Washington, DC – 34 miles -Baltimore - 35 miles * Amenity & Supplies starter pack, coffee and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going. * All beds are made for you with freshly-laundered sheets & towels. House Rules Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking. Dogs allowed if $150 pet fee is paid prior to check-in. Be respectful of the house and contents, the neighbors and neighborhood. 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.

Beachfront, Dog-Friendly w Parking & Mins to DTA

Welcome to our newest listing - The Coastal Cottage on Chesapeake located in the Maritime community of Eastport . This beautiful home features one level living with 3 bedrooms , 2 baths , open kitchen , front porch , large screened in porch and driveway parking for 3 cars and plenty of free off street parking. Walk to all of Eastport restaurants , Historic Downtown , AYC , EYC and USNA . The space One level, 3 bedroom, 2 baths with front porch and large screened porch Guest access We will send you entry info one week out with a personal code for our keyless lock entry .

Chesapeake Cottage in Eastport

For rent unfurnished. Available November 6th. Please note that we will not be doing showings until October as the house is currently rented. 

Top floor bedroom and bathroom remodeled in 2025! This historic gem in the heart of downtown Annapolis is filled with tons of historic character with modern updates and amenities, and includes TWO PARKING SPACES. Located across the street from Saint Mary's and just steps to Spa Creek, City Dock, AYC, and all the shopping and dining on Main Street. The home features a newly renovated kitchen, modern master bathroom, renovated guest bathroom, multiple gas fireplaces, original hardwood floors and second floor sundeck.

6 months, 1 year, 2 year or 3 year. Renter responsible for all utilities. No smoking.

128 Duke of Gloucester St Annapolis, Maryland

$101,578

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