This East Street apartment is centrally located in Annapolis' Historic District, within walking distance of the United States Naval Academy and City Dock. The two-bedroom, 1.5-bathroom property boasts an open-plan layout, a private rooftop deck with city views, in-unit laundry, and a kitchen equipped with a fridge, freezer, microwave, and dishwasher; it comfortably sleeps four guests.
This Annapolis townhome, situated in the President's Hill neighbourhood, is a short walk from West Street and approximately 1.6km from the United States Naval Academy and stadium. The newly renovated two-bedroom property, sleeping up to six guests with a queen sleeper sofa, offers on-site laundry, a private patio, shared gas grill, and firepit, plus off-street parking for two cars.
9.6 20 reviews
Annapolis, MD
12/07 – 13/07
₹83902/nightfor 1 night
Secluded Cozy Cottage In Historic Downtown
2 2
cottage , Annapolis
This charming cottage is located in Annapolis' Historic District, just a short walk from the City Dock and within easy reach of the State House and other key landmarks. The cottage is situated in a quiet neighbourhood, offering a peaceful retreat from the bustling city centre. The cottage is a spacious two-bedroom property that can comfortably accommodate up to eight guests. It features a modern kitchen, a private patio with a BBQ, and a comfortable living area with an electric fireplace, a 55" Roku TV, and a full daybed.
10 75 reviews
Annapolis, MD
23/06 – 25/06
₹101345/nighttotal: ₹202690 (2 )
Recently Renovated Annapolis Home - Conveniently Located
4 2
apartment , Annapolis
This four-bedroom apartment is located in the heart of Annapolis, within easy walking distance of the US Naval Academy and the Navy-Marine Corps Memorial Stadium. It has consistently received excellent reviews from guests, who appreciate its comfortable and spacious accommodation. The apartment has three bathrooms and can comfortably accommodate up to eight guests. It comes equipped with modern amenities, including a fully fitted kitchen, a separate TV/play room, and a private garden with a patio and front porch.
10 71 reviews
Annapolis, MD
28/06 – 30/06
₹78135/nighttotal: ₹156270 (2 )
Charming Historic Home <.75mile To Navy Stadium, 1mile To Usna And Downtown
4 2
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 48 reviews
Annapolis, MD
01/01 – 01/02
₹8382/nighttotal: ₹259842 (31 )
Bungalow Basement In Annapolis
1 2
apartment , Annapolis
This Annapolis basement flat, situated in the Homewood neighbourhood, is a short walk from the United States Naval Academy and West Street, approximately 2.4 kilometres from City Dock. The self-contained apartment sleeps two, boasts a full kitchen with dishwasher, in-unit laundry, Wi-Fi, and a private entrance, offering easy access to the Poplar walking and biking trail and ample street parking.
10 2 reviews
Annapolis, MD
30/06 – 03/07
₹34750/nighttotal: ₹104250 (3 )
Prime Spot Staysimple Comfort, Perfect Location
3 2
apartment , Annapolis
This 3-bedroom flat is located a mere 160 metres from historic Downtown Annapolis, providing straightforward walking access to the U.S. Naval Academy, City Dock, and the Maryland State House. Offering 118 square metres of living space, this accommodation can host up to 8 guests and includes a fully equipped kitchen with a fridge, microwave, and dishwasher, plus air conditioning and parking.
9.7 49 reviews
Annapolis, MD
25/09 – 18/10
₹10629/nighttotal: ₹244467 (23 )
My Annapolis Studio
1 2
apartment , Annapolis
This Annapolis waterfront studio apartment, situated in a peaceful neighbourhood a 6.4km drive from Annapolis' historic city centre, offers convenient access to the city's attractions. The self-contained ground-floor unit features a full kitchen, including a dishwasher, accommodates two guests, and includes a private entrance, brick patio, and a pet-friendly policy (one small pet, restrictions apply).
9.9 84 reviews
Annapolis, MD
28/06 – 30/06
₹74285/nighttotal: ₹148570 (2 )
Historic Chapel Views, Steps To Usna Gate 1 With Private Patio And Off-site Parking
3 2
apartment , Annapolis
This three-bedroom house is situated in Annapolis' Historic District, within a 1.6 km walk of the US Naval Academy and a 0.8 km walk from the Hammond-Harwood House. The property offers a spacious 224 square metre living space, perfect for families or groups of up to seven, with a fully equipped kitchen, a patio, and a barbecue grill.
10 31 reviews
Annapolis, MD
16/07 – 19/07
₹64721/nighttotal: ₹194163 (3 )
Crabby Patty-historic Downtown 3br- Walk To Usna
1 5
apartment , Annapolis
This three-bedroom Annapolis house is centrally located in downtown Annapolis, within easy walking distance of the United States Naval Academy and the historic district. The property boasts a spacious layout, sleeping up to eight guests, and includes a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher; air conditioning is also provided.
Annapolis, MD
20/06 – 18/07
₹45817/nighttotal: ₹1282876 (28 )
4br Family Retreat Near Annapolis W/ Large Yard
4 2
apartment , Annapolis
This Anchorage waterfront community residence is situated just 1.9 kilometres from historic downtown Annapolis, the United States Naval Academy, and waterfront dining. This 172 square metre flat offers four bedrooms, two bathrooms, and accommodates up to eight guests, boasting a large, private, fenced garden with a fire pit and grill, plus access to a single-car garage and two bicycles.
10 10 reviews
Annapolis, MD
03/12 – 06/12
₹69267/nighttotal: ₹207801 (3 )
Stadium-side Annapolis | Chef Kitchen | Sleeps 10
3 10
apartment , Annapolis
This spacious Annapolis townhouse, ideally situated near the U.S. Naval Academy (two miles away) and Navy-Marine Corps Memorial Stadium, offers easy access to Heineman Park and Harts Cove. The 223 square metre property boasts four bedrooms, four bathrooms, and sleeps up to ten guests, featuring a chef's kitchen with GE Café appliances, a finished basement, and access to a community pool; kayaking and paddle boarding are readily available at Harts Cove.
Best Annapolis, MD lodging with a pool
Among the 856 accommodations in Annapolis, MD, here are the 4 best ones with a pool
9.7 18 reviews
Annapolis, MD
27/06 – 29/06
₹31597/nighttotal: ₹63194 (2 )
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.
Annapolis, MD
01/01 – 01/02
₹171252/nighttotal: ₹5308812 (31 )
Lakefront Home With Private Pool, Hot Tub, Outdoor Space, Central Ac, & W/d
6 2
apartment , Highland Beach
This expansive 604 square meter luxury apartment in Highland Beach offers exclusive waterfront living on Lake Ogleton, providing direct access to the Chesapeake Bay and a mere 4 kilometers from Annapolis's historical attractions, including the Maritime Museum and Colonial Players. Boasting 6 bedrooms and 4 bathrooms to accommodate up to 12 guests, this family-friendly residence features a gourmet kitchen with two dishwashers and double refrigerators, multiple living areas with fireplaces, a third-floor rooftop with panoramic views, a private pier, a seasonal swimming pool, and a hot tub for an exceptional stay.
10 5 reviews
Annapolis, MD
21/08 – 24/08
₹31628/nighttotal: ₹94884 (3 )
Spa Creek Condo | Pool, Deck & Parking
1 2
apartment , Annapolis
This Eastport condo provides waterfront living on Spa Creek, a mere 500-metre walk from Downtown Annapolis and the US Naval Academy. This one-bedroom flat, accommodating up to four guests, features a fully equipped kitchen, air conditioning, a swimming pool, garden, and parking for two vehicles, with a covered deck offering direct Spa Creek views and seasonal access to a shared dock.
9.4 100 reviews
Annapolis, MD
19/06 – 22/06
₹48143/nighttotal: ₹144429 (3 )
Brick Georgian W Pool, Pet Friendly 1 Mile To All!
1 2
apartment , Annapolis
This charming three-bedroom house is situated in a peaceful waterfront neighbourhood, just a short distance from Annapolis' historic downtown, the Naval Academy, and the Navy Marine Corps Stadium. The property has consistently received excellent ratings for its location, cleanliness, and overall experience. The house comfortably sleeps seven guests and features a well-equipped kitchen, a private pool, and a patio with a barbecue. Guests can enjoy a range of amenities, including a piano, board games, and a formal dining room, as well as access to kayaks and a canoe for exploring the nearby waterways.
Best family friendly Annapolis, MD lodging
Among the 856 accommodations in Annapolis, MD, here are the 4 best for families
10 7 reviews
Annapolis, MD
19/06 – 21/06
₹62430/nighttotal: ₹124860 (2 )
Fenced + Fire Pit + Coffee Bar 2 Miles From Usna
1 2
apartment , Annapolis
This pet-friendly flat in Annapolis is situated conveniently 3 minutes by car from the Navy-Marine Corps Memorial Stadium and 7 minutes by car from Historic Downtown Annapolis. This newly renovated four-bedroom, three-bathroom accommodation comfortably sleeps eight guests and features a fully stocked kitchen, a screened-in outdoor lounge with a television, and a wood-burning firepit, with a propane grill available for use.
9.3 58 reviews
Annapolis, MD
21/08 – 24/08
₹14214/nighttotal: ₹42642 (3 )
Gaia House
2 2
house , Annapolis
Gaia House, in Annapolis, is situated 6 kilometres from Annapolis Harbour and within a 32-48 kilometre radius of Baltimore attractions including the Inner Harbour and Historic Ships in Baltimore. This two-bedroom property, offering 9 square metres of floor space, sleeps seven guests and features a fully equipped kitchen, private parking, Wi-Fi, air conditioning, and a patio with quiet street views.
8.8 11 reviews
Annapolis, MD
12/11 – 14/11
₹38972/nighttotal: ₹77944 (2 )
Walk To Everything Historic Arts District
2 2
house , Annapolis
This Annapolis holiday home is located in the Historic Arts District, 3.1km from Annapolis Harbour and within 32-48km of Baltimore attractions. The 139 square metre property offers a two-bedroom layout sleeping up to 11 guests, boasting a fully equipped kitchen, private parking, and a terrace; ideal for families exploring Annapolis and its surrounding areas.
10 40 reviews
Annapolis, MD
16/07 – 19/07
₹45693/nighttotal: ₹137079 (3 )
Annapolis Main Street Modern Apartment
1 4
apartment , Annapolis
This Annapolis apartment rental is situated in the Main Street district, a 1.6km walk from the United States Naval Academy and a 0.5km walk from the Hillman parking garage, offering views of the Maryland State House. The two-bedroom, one-bathroom flat sleeps four, features keyless entry, complimentary coffee and snacks, and a dishwasher; a connecting apartment is available for larger groups.
Frequently asked questions about accommodations in Annapolis, MD
What are the top attractions and must-see sites in Annapolis, MD?
You definitely want to visit the United States Naval Academy, a beautiful campus with a rich history. The Maryland State House is another must-see, being the oldest state capitol building in continuous legislative use in the United States. And of course, you can't miss the Annapolis City Dock, a vibrant waterfront area with shops, restaurants, and plenty of boat watching.
What are the most convenient modes of transportation within Annapolis, MD?
Annapolis is a very walkable city, so you can easily get around on foot. There's also a good public bus system, the Annapolis Area Transit (AAT), that can take you to most places. If you're planning to explore further afield, consider renting a car. And don't forget about the water taxis - a fun and scenic way to get around the harbour.
What outdoor activities and adventures are popular in and around Annapolis, MD?
For outdoor enthusiasts, there are plenty of options. You can go kayaking or paddleboarding on the Chesapeake Bay, explore the trails at Quiet Waters Park, or visit the Sandy Point State Park for a day of sun and sand. And if you're feeling adventurous, try sailing on the bay - there are plenty of charter companies offering trips.
What types of accommodations are available in Annapolis, MD?
You'll find a range of accommodation options in Annapolis, from budget-friendly motels and guesthouses to luxurious hotels and waterfront resorts. There are also plenty of vacation rentals available if you're looking for something more spacious or unique.
When is the best time to visit Annapolis, MD?
Spring and autumn are generally the most pleasant times to visit Annapolis, with mild temperatures and less crowds. If you're looking for warm weather and outdoor activities, summer is a good option. And if you enjoy the festive atmosphere, winter offers the charm of the holiday season.
What local dishes and culinary experiences are a must-try in Annapolis, MD?
You have to try some fresh seafood when you're in Annapolis! The Chesapeake Bay is famous for its blue crabs, so make sure to order a crab cake or steamed crabs. And don't forget to try the local oysters, they're delicious! For a sweet treat, head to the famous Carvel ice cream shop, a local favourite.
Destinations nearby
Best Annapolis, MD accommodations with a balcony
9.8 8 reviews
Annapolis, MD
25/06 – 28/06
₹60538/nighttotal: ₹181614 (3 )
Cute Bungalow Blocks To Stadium
2 2
apartment , Annapolis
This Annapolis holiday home in Admiral Heights is situated 0.8km from People's Brewer Hill Cemetery and 2.6km from the United States Naval Academy. The 111 square metre property sleeps six guests and boasts three bedrooms, two bathrooms, a fully equipped kitchen, a private balcony, a garden with barbecue, and parking; enjoy nearby attractions such as the Navy-Marine Corps Memorial Stadium and Helen Avalynne Tawes Garden.
10 16 reviews
Annapolis, MD
01/01 – 01/02
₹33211/nighttotal: ₹1029541 (31 )
Historic Annapolis Home | 2 Blocks To Main St
3 2
apartment , Annapolis
This Annapolis holiday home is situated in the Historic District, within a 0.9km walk of the US Naval Academy and Maynard-Burgess House, and under 0.5km from the Maryland Federation of Art and Ellen O Moyer Nature Park. The 1174 square metre property boasts four bedrooms, two bathrooms, sleeps nine guests, and includes a fully equipped kitchen, private garden, terrace, free Wi-Fi, and barbecue facilities.
10 26 reviews
Annapolis, MD
23/06 – 25/06
₹96572/nighttotal: ₹193144 (2 )
Cozy, Waterfront, 5br 4ba House W 2 Decks Near Usna & Downtown
5 2
apartment , Highland Beach
This Highland Beach waterfront property, a five-minute walk from the Chesapeake Bay and historic Highland Beach, is situated a short drive from Annapolis city centre, the United States Naval Academy, and Quiet Waters Park. The five-bedroom, four-bathroom house sleeps ten guests, boasts a well-equipped kitchen, two spacious decks with stunning waterfront views, a tennis court, ample parking, and offers access to free Wi-Fi and a home office/fitness room.
9.8 29 reviews
Annapolis, MD
27/06 – 29/06
₹66058/nighttotal: ₹132116 (2 )
Walk To Main Street, City Dock And Usna Gate 1 From Historic Catch 22 With Private Patio
3 2
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.
Best Annapolis, MD accommodations with a kitchen
10 6 reviews
Annapolis, MD
03/12 – 06/12
₹56384/nighttotal: ₹169152 (3 )
5 Br House With Ev Charger Near Downtown Annapolis
1 10
apartment , Annapolis
Voyagers' Nest is a five-bedroom property located approximately 800 meters from downtown Annapolis and the U.S. Naval Academy, offering convenient access to the historic waterfront. This spacious house accommodates up to 12 guests with five bedrooms, two bathrooms, two living rooms, a fully equipped kitchen, a private fenced garden with a patio, whole-house water filtration, high-speed Wi-Fi, and ample parking including a driveway and free street parking.
Annapolis, MD
03/12 – 06/12
₹86092/nighttotal: ₹258276 (3 )
Annapolis Gem- Tranquil 4 Br Murray Hill Victorian
4 10
apartment , Annapolis
This historic 1911 Murray Hill apartment is located approximately 1.6 kilometres from the United States Naval Academy and offers convenient access to downtown Annapolis, with Church Circle 4 blocks away, Main Street 5 blocks away, and Annapolis City Dock 12 blocks away. This four-bedroom, two-and-a-half-bathroom property accommodates up to ten guests and features an open-plan kitchen, living, and dining area, a patio with a barbecue, a front porch swing, and is equipped with air conditioning, a dishwasher, and Wi-Fi.
9.7 227 reviews
Annapolis, MD
23/06 – 25/06
₹31409/nighttotal: ₹62818 (2 )
Beautiful Condo - Water View Near City Dock
1 2
apartment , Annapolis
This one-bedroom apartment is conveniently located in Eastport, Annapolis, within walking distance of Spa Creek and the US Naval Academy. The apartment has received excellent ratings for location, cleanliness, and overall user experience. The 57 square metre apartment comfortably accommodates up to four guests. The apartment offers a range of amenities, including a private pool, access to a water park and outdoor pool, a fully equipped kitchen, a terrace, a garden, a spa, parking, and internet access.
10 60 reviews
Annapolis, MD
06/07 – 30/08
₹45377/nighttotal: ₹2495735 (55 )
Sleeps 10 | Private Bar & Fenced Yard
1 2
apartment , Annapolis
This charming home is located in West Annapolis, just 2.4 kilometres from the Naval Academy, 2.6 kilometres from downtown Annapolis, and 0.5 kilometres from the Navy Stadium. The property benefits from excellent ratings for location, cleanliness, and overall experience. The four-bedroom house comfortably accommodates up to ten guests and features a spacious living room, a basement lounge area, and a private bar and gym in the garage. Guests can enjoy a fully equipped kitchen, a fenced-in backyard, and a fitness centre, all within walking distance of restaurants, shops, and attractions.