All Tucked Inn, a one-bedroom Annapolis property, is situated 4km from Annapolis Harbour and 47km from Baltimore attractions including the Inner Harbour and Camden Yards. This self-catering house sleeps 15 guests and boasts three bathrooms, a fully equipped kitchen with dishwasher, free Wi-Fi, and on-site parking; enjoy nearby Baltimore-Washington International Airport (32km).
10 106 reviews
Annapolis, MD
29/06 – 01/07
₹26681/nighttotal: ₹53362 (2 )
Quaint In The Heart Of Annapolis
1 4
apartment , Annapolis
This two-bedroom Annapolis home, situated less than 5km from the city centre, the United States Naval Academy, Annapolis Mall, St John's College, and the Navy-Marine Corps Memorial Stadium, offers a peaceful retreat on a quiet residential street. The fully-remodelled property sleeps four, boasts a modern open-plan kitchen-living area with a dishwasher and 55-inch smart TV, and includes two off-street parking spaces.
Annapolis, MD
25/06 – 25/07
₹49706/nighttotal: ₹1491180 (30 )
New! Private, Family-friendly Home Near Usna
3 2
house , Annapolis
This family-friendly detached house is located in Annapolis, 5.15 kilometres from Annapolis Harbour and 38.62 kilometres from Addison Road-Seat Pleasant. This accommodation offers 111 square metres of living space with 3 bedrooms, 2 bathrooms, and a capacity for 13 guests, featuring a fully equipped kitchen, air conditioning, a garden, and private parking.
10 125 reviews
Annapolis, MD
06/08 – 10/08
₹97886/nighttotal: ₹391544 (4 )
Charming Annapolis Victorian
6 10
apartment , Annapolis
This six-bedroom house is located in a peaceful neighbourhood, just a short walk from downtown Annapolis, the US Naval Academy, and the USNA Stadium. It has received excellent ratings for location, cleanliness, and overall experience. The house offers three floors of living space, comfortably accommodating up to 12 guests. It features a fully equipped kitchen, a jacuzzi, a terrace, a garden, and ample parking, making it ideal for families or groups seeking a comfortable and convenient stay.
9.9 26 reviews
Annapolis, MD
12/07 – 30/08
₹16390/nighttotal: ₹803110 (49 )
Xl Annapolis Suite (Br/lr), Private Entry & Bath
1 2
apartment , Annapolis
This Annapolis guesthouse is conveniently located minutes from the United States Naval Academy and Annapolis city centre, offering easy access to Annapolis Town Centre and Route 50, and is within walking distance of Navy-Marine Corps Memorial Stadium. The self-contained suite comprises a bedroom, bathroom, sitting/TV area, and dining space, sleeping up to two guests and including a fridge, microwave, and Wi-Fi; potential access to a patio with dining and grilling facilities is also available.
10 72 reviews
Annapolis, MD
03/12 – 06/12
₹63098/nighttotal: ₹189294 (3 )
Charming Historic Home <.75mile To Navy Stadium, 1mile To Usna And Downtown
1 10
apartment , Annapolis
This family-friendly holiday home is located in Annapolis, just 1.6km from People's Brewer Hill Cemetery, Helen Avalynne Tawes Garden, and Maryland Hall for Creative Arts, and 3.2km from the U.S. Naval Academy. Guests have consistently rated this property excellent for location, cleanliness, and overall user experience. The four-bedroom property spans 372 square metres and comfortably accommodates up to 14 guests. This spacious house offers a range of amenities, including a fully equipped kitchen, a private garden with a barbecue, a tennis court, and a terrace, making it perfect for families and groups seeking a relaxing and enjoyable stay.
9.8 95 reviews
Annapolis, MD
29/08 – 04/09
₹67541/nighttotal: ₹405246 (6 )
Walkable To Main Street At Seashell In The City With 2 Parking Spots
4 2
apartment , Annapolis
This house is located in Annapolis' Historic District, a short walk from the U.S. Naval Academy and Maynard-Burgess House, and is within 5 minutes of the Maryland Federation of Art and Ellen O. Moyer Nature Park at Back Creek. The property has received excellent ratings for location, cleanliness and overall user experience. This 4-bedroom home can accommodate up to 8 guests, making it ideal for families or groups of friends. The house includes a fully equipped kitchen, a garden, a terrace, free Wi-Fi, parking and a spa, ensuring a comfortable and enjoyable stay.
9.6 158 reviews
Annapolis, MD
15/08 – 22/08
₹25637/nighttotal: ₹179459 (7 )
King George Downtown Annapolis Getaway
2 2
apartment , Annapolis
This flat is situated in the centre of Annapolis, just 2.2 kilometres from the harbour and within easy reach of Baltimore’s attractions. It has received excellent ratings for location, cleanliness and overall experience. The accommodation offers a comfortable and well-equipped space, including a fully fitted kitchen, a balcony and a garden. Guests can enjoy free Wi-Fi, air conditioning, parking and barbecue facilities.
9.8 12 reviews
Annapolis, MD
29/06 – 01/07
₹40525/nighttotal: ₹81050 (2 )
Weems Creek Cottage, Annapolis Waterfront
1 4
house , Annapolis
Weems Creek Cottage offers a waterfront property in Annapolis, Maryland, situated 4.3km from Annapolis Harbour and 32km from Baltimore-Washington International Thurgood Marshall Airport. This self-catering house boasts 65 square metres of floor space, sleeping up to 7 guests in one bedroom and one bathroom, and includes amenities such as Wi-Fi, parking, a fully equipped kitchen, and a spa.
9.9 221 reviews
Annapolis, MD
12/07 – 13/07
₹62143/nightfor 1 night
Secluded Cottage_ A+ Amenities In Historic Dwntwn
2 2
apartment , Annapolis
This charming cottage is located in Annapolis' historic Cornhill district, just a short walk from the State House and the city centre, offering a peaceful retreat in a vibrant area. It has received excellent ratings for location, cleanliness and overall experience. The cottage has a spacious open-plan layout, comfortably accommodating up to eight guests. The well-equipped kitchen is perfect for preparing meals, and the private laundry, garden and air conditioning add to the comfort of your stay.
9.8 7 reviews
Annapolis, MD
12/07 – 13/07
₹177272/nightfor 1 night
Historic Annapolis Charmer <1mile To Nmc Stadium
6 2
apartment , Annapolis
This Annapolis apartment, situated a short walk from the city centre and a short drive (approximately 1-2km) from the United States Naval Academy and Navy-Marine Corps Stadium, offers convenient access to Annapolis's key attractions. This spacious 465 square metre dwelling boasts five bedrooms, five bathrooms, and sleeps up to 21 guests, featuring multiple living areas, a well-equipped kitchen, a garden, tennis court, parking, and proximity to Ego Alley, Great Frogs Winery, and Helen Avalynne Tawes Garden.
10 6 reviews
Annapolis, MD
25/06 – 28/06
₹49201/nighttotal: ₹147603 (3 )
Historic Dog-friendly Home 2 Blocks To Main St
1 2
apartment , Annapolis
This one-bedroom apartment is situated in Historic Annapolis, just 0.8 km from the city's main street and 1.6 km from the United States Naval Academy. The apartment offers a comfortable living space with a king-size bed, a twin futon, and a family room with another twin futon, ideal for accommodating up to four guests.
Best family friendly Annapolis, MD vacation rentals
Among the 758 accommodations in Annapolis, MD, here are the 4 best family friendly rentals
10 1 review
Annapolis, MD
29/06 – 01/07
₹58450/nighttotal: ₹116900 (2 )
Luxury Rooftop Pool & Dock Steps To Downtown
2 4
house , Annapolis
This luxury condominium in Annapolis is located a 13-minute walk from Annapolis Harbour and 41.8 kilometres from Baltimore's Inner Harbour. This air-conditioned holiday home offers 49 square metres of living space with two bedrooms, accommodating up to seven guests, and features a rooftop pool with sea views, private dock access, a well-equipped kitchen, and a fireplace.
9.8 20 reviews
Annapolis, MD
06/11 – 08/11
₹153483/nighttotal: ₹306966 (2 )
Chesapeake Comfort, Annapolis.
3 2
apartment , Annapolis
This Annapolis holiday home is centrally located, less than 0.5 km from Peters Cove and 3.2 km from the United States Naval Academy. The 186 square metre property boasts three bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, private patio, free Wi-Fi, and access to a spa.
10 19 reviews
Annapolis, MD
03/12 – 06/12
₹131204/nighttotal: ₹393612 (3 )
Steps To Downtown Annapolis & Spa Creek From Stunning Craftsman With Game Room, Parking And Backyard
4 10
apartment , Annapolis
This charming lighthouse is situated in Eastport, Annapolis, a short walk from downtown Annapolis (1.1 km), the US Naval Academy (1.4 km), and Fourth Street shops and restaurants (0.3 km). This property enjoys excellent user ratings and offers a comfortable and convenient stay. The lighthouse provides 4 bedrooms and 4 bathrooms, accommodating up to 12 guests. Guests can enjoy a range of amenities and activities, including a gourmet kitchen, a recreation room, multiple outdoor spaces, and family-friendly features.
10 32 reviews
Annapolis, MD
11/09 – 19/09
₹64345/nighttotal: ₹514760 (8 )
2026 Commissioning Week Promo: Book 6 Nights, Get The 7th Free
3 4
apartment , Annapolis
This Annapolis holiday home is centrally located, within 2km of Spa Creek and the United States Naval Academy, offering easy access to the Annapolis Maritime Museum and the Maynard-Burgess House. The 139 square metre property sleeps eight guests in three bedrooms, two bathrooms, and features a fully equipped kitchen, terrace, garden, spa, parking, and Wi-Fi.
Best Annapolis, MD vacation rentals with a pool
Among the 758 accommodations in Annapolis, MD, here are the 4 best rentals with a pool
9.8 27 reviews
Annapolis, MD
17/09 – 22/09
₹170541/nighttotal: ₹852705 (5 )
Spacious Luxe Usna Home - Pool, Hot Tub, Grill
5 1
apartment , Annapolis
This seven-bedroom Annapolis property, situated in the Murray Hill district, is less than 1.6km from the US Naval Academy and the Annapolis Civil Rights Plaque. This smoke-free holiday home boasts 307 square metres of floor space, offering four bathrooms, a fully equipped kitchen, garden, parking and sleeps up to fourteen guests.
9.7 18 reviews
Annapolis, MD
25/06 – 28/06
₹36147/nighttotal: ₹108441 (3 )
Eastport Apartment
1 2
apartment , Annapolis
This Annapolis apartment, ideally located in the city centre, offers easy access to the Annapolis City Dock and the United States Naval Academy, both within a short walking distance (precise distances unstated). The one-bedroom flat sleeps four, includes a kitchen, air conditioning, parking, and a swimming pool, providing a comfortable base for exploring this historic Maryland city.
9.9 38 reviews
Annapolis, MD
06/08 – 10/08
₹165859/nighttotal: ₹663436 (4 )
The Retreat @ Back Creek
1 10
apartment , Annapolis
This five-bedroom apartment is located in Eastport, a short walk from Annapolis' historic downtown and bustling City Dock. It has received excellent ratings for location, cleanliness and user experience. The apartment has three bathrooms and can accommodate up to sixteen guests. It offers a range of amenities, including a heated indoor pool, a spacious great room, a private patio, and a large recreation room with a bar and ping pong table.
9.9 43 reviews
Annapolis, MD
17/09 – 22/09
₹69704/nighttotal: ₹348520 (5 )
Beautiful House In The Best Location!
1 1
apartment , Annapolis
This modern three-bedroom, three-bathroom house in Annapolis's Eastport district is located minutes from the city centre, the United States Naval Academy, and the Chesapeake Bay. Sleeping eight guests, this property boasts a heated saltwater pool (open mid-May to Labor Day), a spacious garage, and benefits from the 'Naval Commissioning Week' offer (17th-23rd May: 7th night free).
Frequently asked questions about holiday rentals in Annapolis, MD
What are the top family-friendly attractions in Annapolis, MD?
The Maryland State House is fascinating for kids, and the Annapolis Maritime Museum has lots of hands-on activities. For a fun day out, head to Sandy Point State Park, there's a great beach and plenty of space for kids to run around.
What are the best Airbnb and vacation rentals in Annapolis, MD?
When is the best time to book a vacation rental in Annapolis, MD?
Book your vacation rental as early as possible, especially if you're travelling during peak season, which is from May to October. You'll have more choice and potentially better prices.
What are the most popular Airbnbs in Annapolis, MD?
What events or festivals should visitors check out in and around Annapolis, MD?
The Annapolis Maritime Museum hosts a series of events throughout the year, and the annual Annapolis Arts Festival is a highlight in the summer. Check out the local calendar for other events like the Annapolis Boat Show.
What are the best vacation rentals with a pool in Annapolis, MD?
What are the best budget-friendly activities in Annapolis, MD?
Take a walk along the Annapolis City Dock, it's free and offers stunning views. The Naval Academy is also free to visit. For a picnic, head to Quiet Waters Park, it's a beautiful spot.
What are the best rentals for families and kids in Annapolis, MD?
What are the best restaurants with local dishes in Annapolis, MD?
For fresh seafood, try Cantler's Riverside Inn or The Chart House. If you're looking for something more casual, try The Annapolis Market House, they have a great selection of local produce.
What are the best rentals or Airbnbs with a jacuzzi in Annapolis, MD?
What are the best walking or cycling routes in Annapolis, MD?
The Annapolis Loop Trail is a great option for cyclists, it's about 13km long and takes you past some of the city's most scenic spots. For a shorter walk, try the scenic path along the Spa Creek.
Are there pet-friendly attractions in Annapolis, MD?
Many of the parks in Annapolis are pet-friendly, including Quiet Waters Park and the City Dock. You'll find plenty of dog-friendly restaurants and cafes too.
What are the benefits of choosing a vacation rental in Annapolis, MD?
Vacation rentals offer more space and privacy than hotels. They can also be a more affordable option, especially if you're travelling with a group. Plus, you can often find rentals in great locations.
What are the top sports attractions and facilities in Annapolis, MD?
The US Naval Academy is a big draw for sports fans, with its football and basketball teams. The city also has a number of public parks with sports facilities, like the Quiet Waters Park.
Destinations nearby
Best Annapolis, MD holiday rentals with a balcony
10 10 reviews
Annapolis, MD
15/08 – 22/08
₹31648/nighttotal: ₹221536 (7 )
Downtown Furnished Apartment - Walking Distance To Restaurants
1 2
apartment , Annapolis
This smoke-free flat is located in Annapolis' Historic District, just under a kilometre from the Maynard-Burgess House and the U.S. Naval Academy, and within 500 metres of the Ellen O. Moyer Nature Park and the Maryland Federation of Art. It has received excellent reviews from previous guests. This comfortable apartment can accommodate up to four guests and features a fully-equipped kitchen, a terrace, and a garden. You can enjoy stunning city views from the rooftop terrace and explore the nearby art galleries and nature parks.
9.8 41 reviews
Annapolis, MD
11/09 – 19/09
₹104117/nighttotal: ₹832936 (8 )
Beachfront Home Minutes To Downtown Annapolis Dogs Ok
3 4
cottage , Annapolis
This charming cottage is located just 4 km from downtown Annapolis and 4.5 km from the US Naval Academy, offering a peaceful escape close to the city's attractions. It has received excellent guest reviews, making it a popular choice for travellers seeking a comfortable and well-equipped stay. The cottage comfortably sleeps 8 guests and features 3 bedrooms and 2 bathrooms, providing ample space for families or groups. Enjoy the private beach with direct bay access, a gourmet kitchen, a spacious garden, and a range of amenities including paddle boards, life jackets, and a barbecue grill.
9.8 29 reviews
Annapolis, MD
29/06 – 01/07
₹59712/nighttotal: ₹119424 (2 )
Walk To Main Street, City Dock And Usna Gate 1 From Historic Catch 22 With Private Patio
3 4
apartment , Annapolis
This three-bedroom townhouse is located in the historic district of Annapolis, just 0.5 kilometres from the city dock and within 0.3 kilometres of the State Circle, the Annapolis Yacht Club, and the Naval Academy. The property has received excellent reviews from previous guests. The home has a spacious and open floor plan, comfortably accommodating up to nine guests. It features a fully equipped kitchen, a private patio with a gas grill, and a balcony, along with modern amenities such as three smart TVs, high-speed Wi-Fi, cable TV, a washer and dryer, and keyless entry.
9.6 14 reviews
Annapolis, MD
15/08 – 22/08
₹47095/nighttotal: ₹329665 (7 )
Downtown Pinkney House W/parking
2 2
apartment , Annapolis
This Annapolis Historic District property is situated less than a kilometre from Annapolis City Dock and the United States Naval Academy, offering easy access to 14 Fleet Street and The Colonial Players. The two-bedroom, three-bathroom house sleeps four guests and includes a fully equipped kitchen with dishwasher, in-unit laundry, a balcony, and parking; enjoy nearby attractions and on-site entertainment.
Best Annapolis, MD holiday rentals with parking
9.8 298 reviews
Annapolis, MD
24/07 – 29/07
₹41548/nighttotal: ₹207740 (5 )
Annapolis Condominium In The Heart Of The Historic Center
3 3
apartment , Annapolis
This Annapolis apartment, situated in the Historic District, is less than 1.6km from the United States Naval Academy and Maynard-Burgess House, offering easy access to the Ellen O. Moyer Nature Park at Back Creek and the Maryland Federation of Art. The 130 square metre self-catering property features three bedrooms, two bathrooms, sleeps six, and includes a private patio, garden access, parking, and a fully equipped kitchen with a dishwasher; a spa is also available on site.
9.9 73 reviews
Annapolis, MD
12/07 – 13/07
₹43624/nightfor 1 night
Harbor’s Edge Retreat: Walk To Main St & Academy
1 2
apartment , Annapolis
This newly renovated Annapolis retreat is centrally located, within walking distance of Annapolis City Dock, Ego Alley, and the United States Naval Academy. The three-bedroom house sleeps six, boasts a fully equipped Samsung kitchen, in-unit laundry, high-speed WiFi, a fenced backyard, and off-premises garage parking options nearby.
9.9 94 reviews
Annapolis, MD
15/08 – 22/08
₹20633/nighttotal: ₹144431 (7 )
King George Hideaway 1st Floor
1 2
apartment , Annapolis
This one-bedroom flat is located in the centre of Annapolis, just 0.2km from the USNA Gate 2 and a short walk from Ego Alley and Main Street. The property has received excellent ratings for location, cleanliness, and overall experience. The flat comfortably accommodates four guests with a queen-size bed and a pull-out sofa. The kitchen is fully equipped with a fridge, freezer, microwave oven, and dishwasher, perfect for preparing meals during your stay.
10 33 reviews
Annapolis, MD
01/07 – 08/07
₹63474/nighttotal: ₹444318 (7 )
All-stop. Rental Midships.
2 2
apartment , Annapolis
This two-bedroom townhome is located in the heart of Downtown Annapolis, just a short walk from the Naval Academy, City Dock, and other major attractions. The property has received excellent ratings for location, cleanliness, and overall experience. The townhome can comfortably accommodate up to four guests and features a fully equipped kitchen, multiple outdoor spaces, and comfortable bedrooms. Guests can enjoy complimentary amenities such as coffee, linens, and toiletries, as well as free parking options.
