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Annapolis, MD accommodations
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856 Lodgings in Annapolis, MD

Best Annapolis, MD lodging with a pool

Among the 856 accommodations in Annapolis, MD, here are the 4 best ones with a pool

Semper Fi Condo - Annapolis, MD
10 2 reviews
Annapolis, MD
16/07 – 19/07
967 ﺩ.ﺇ/nighttotal: 2901 ﺩ.ﺇ (3 )

Semper Fi Condo

1 4
apartment , Annapolis
This Annapolis flat offers a prime location just minutes from downtown, the Royal Naval Academy, and waterfront attractions, with Quiet Waters Park and its dog beach approximately 1.3 kilometres away.
This pet-friendly condo for four guests features air conditioning, a full kitchen with fridge, freezer and microwave, two bathrooms, a private balcony, and access to communal swimming pool and gym facilities, with free parking and secure code-entry building access.
Annapolis Waterfront Condo - Unit #: A-203 - Annapolis, MD
9.9 321 reviews
Annapolis, MD
21/08 – 24/08
1173 ﺩ.ﺇ/nighttotal: 3519 ﺩ.ﺇ (3 )

Annapolis Waterfront Condo - Unit #: A-203

1 2
apartment , Annapolis
This one-bedroom flat is located just 1.5 kilometres from downtown Annapolis and the US Naval Academy, making it easy to explore the city's historical attractions and vibrant waterfront. The property has received excellent ratings for its location, cleanliness, and overall experience.
The flat can accommodate up to four guests and features a fully equipped kitchen, washer and dryer, and a private deck with stunning views. Guests can enjoy the on-site swimming pool, relax in the garden, or take advantage of free parking.
Spa Creek Waterfront | Pool & Parking - Annapolis, MD
10 7 reviews
Annapolis, MD
21/08 – 24/08
1270 ﺩ.ﺇ/nighttotal: 3810 ﺩ.ﺇ (3 )

Spa Creek Waterfront | Pool & Parking

1 2
apartment , Annapolis
This Eastport condo offers waterfront living on Spa Creek, a mere 800 meters' walk to Downtown Annapolis and the US Naval Academy.
This two-bedroom flat accommodates up to four guests and features a communal swimming pool (seasonal), a fitness centre, and complimentary parking for two cars, with a covered deck providing water views.
Luxury Condo | Walk To Usna • Rooftop Pool - Annapolis, MD
10 3 reviews
Annapolis, MD
30/06 – 03/07
1712 ﺩ.ﺇ/nighttotal: 5136 ﺩ.ﺇ (3 )

Luxury Condo | Walk To Usna • Rooftop Pool

1 2
apartment , Annapolis
This Eastport flat offers waterfront living on Spa Creek with marina access, situated a mere 480 metres from downtown Annapolis and 800 metres from the Naval Academy.
This luxury condo sleeps four guests, featuring a rooftop pool with city skyline views, two complimentary parking spaces, a fully equipped kitchen with a coffee station, and a spa-inspired bathroom with a rainfall shower.

Best family friendly Annapolis, MD lodging

Among the 856 accommodations in Annapolis, MD, here are the 4 best for families

Elegant & Bright Historic Home 3br/2,5ba, 2 Kings, 1 Queen, 5 Min To Usna - Annapolis, MD
10 3 reviews
Annapolis, MD
19/06 – 21/06
2817 ﺩ.ﺇ/nighttotal: 5634 ﺩ.ﺇ (2 )

Elegant & Bright Historic Home 3br/2,5ba, 2 Kings, 1 Queen, 5 Min To Usna

3 2
apartment , Annapolis
This 3-bedroom flat for 7 guests offers an unbeatable location in Annapolis's historic district, a mere 5-minute walk from the US Naval Academy and within 1 minute of the Maryland State House and Annapolis Town Dock.
This 125 square meter residence features a fully equipped kitchen with stainless-steel appliances, a lounge with a fireplace, two king-sized bedrooms, and three bathrooms, with free WiFi and air conditioning provided.
Secluded Cozy Cottage In Historic Downtown - Annapolis, MD
9.6 20 reviews
Annapolis, MD
30/06 – 03/07
2670 ﺩ.ﺇ/nighttotal: 8010 ﺩ.ﺇ (3 )

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.
Historic Annapolis Charmer <1mile To Nmc Stadium - Annapolis, MD
9.8 7 reviews
Annapolis, MD
03/12 – 06/12
4904 ﺩ.ﺇ/nighttotal: 14712 ﺩ.ﺇ (3 )

Historic Annapolis Charmer <1mile To Nmc Stadium

6 10
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.
Waterfront Home With Private Dock, Community Beach - Annapolis, MD
10 7 reviews
Annapolis, MD
23/06 – 25/06
2200 ﺩ.ﺇ/nighttotal: 4400 ﺩ.ﺇ (2 )

Waterfront Home With Private Dock, Community Beach

3 2
apartment , Highland Beach
This four-bedroom, two-bathroom waterfront property in Oyster Harbour, Annapolis, is situated approximately 6.4 km from Annapolis city centre and 7.2 km from the United States Naval Academy.
The self-catering holiday home sleeps eight guests and boasts a private dock with kayaks and paddleboards, a garden with firepit, modern kitchen, and access to neighbourhood amenities including a swimming beach, gym, and playgrounds.

Frequently Asked Questions about accommodations in Annapolis, MD

  • What are the top attractions and must-see sites in Annapolis, MD?

    Annapolis is packed with history and charm! You absolutely have to visit the United States Naval Academy, the Maryland State House, and the historic Annapolis City Dock. Don't miss the chance to explore the beautiful gardens at the William Paca House and Garden.
  • What are the best accommodations in Annapolis, MD?

    Among the accommodations in Annapolis, MD, Step Out To Main Street From A Chic Loft, Graduate By Hilton Annapolis and Springhill Suites By Marriott Annapolis are the most popular ones.

  • Which cultural festivals and seasonal events should visitors attend in Annapolis, MD?

    The Annapolis Summerfest is a big one, with live music and arts and crafts. You'll also want to check out the Annapolis Maritime Museum's annual Seafood Festival, and the Annapolis Wine Festival in the spring. And, of course, there's the annual Annapolis Boat Show, which is a must-see for any sailing enthusiast.
  • What are the best accommodations with a pool in Annapolis, MD?

  • What are the most convenient modes of transportation within Annapolis, MD?

    Annapolis is a very walkable city, especially in the downtown area. You can easily get around on foot or by bike. If you're coming from further afield, the Annapolis Area Transit buses are a good option, and you can also get around by taxi or ride-sharing services.
  • What are the best accommodations with a jacuzzi in Annapolis, MD?

  • What outdoor activities and adventures are popular in and around Annapolis, MD?

    Annapolis is right on the Chesapeake Bay, so you can enjoy a variety of water activities, like sailing, kayaking, and fishing. If you're looking for something a little more adventurous, you can go hiking or biking on the scenic trails at Quiet Waters Park or the Anne Arundel County Natural Resources Park.
  • What are the best accommodations for families and kids in Annapolis, MD?

  • What types of accommodations are available in Annapolis, MD?

    You've got a good range of options in Annapolis. There are plenty of hotels, from budget-friendly to luxury, as well as bed and breakfasts, guesthouses, and even some vacation rentals. You can find something to suit any taste and budget.
  • What are the best pet friendly accommodations in Annapolis, MD?

  • When is the best time to visit Annapolis, MD?

    Spring and autumn are ideal, with pleasant weather and fewer crowds. Summer is beautiful, but it can get hot and humid, and the city is very busy. If you want to see the city decked out for the holidays, then winter is a good time to visit, but be prepared for chilly temperatures.
  • What are the best accommodations with parking in Annapolis, MD?

  • What local dishes and culinary experiences are a must-try in Annapolis, MD?

    You have to try the fresh seafood, of course! Crab cakes are a local favourite, and you can find them at many restaurants in the city. Also, don't miss the chance to enjoy a delicious meal at one of the many waterfront restaurants, with stunning views of the Chesapeake Bay.
  • In which part of Annapolis, MD should you consider renting accommodation?

    If you want to be in the heart of the action, then downtown Annapolis is the place to be. If you prefer a quieter stay, then you might want to consider staying in the historic district, or even in one of the nearby suburbs, like Eastport or West Annapolis.

Destinations nearby

Best Annapolis, MD accommodation with a balcony

Cute And Close To Downtown! Off Street Parking W/ Short Walk To Academy/stadium - Annapolis, MD
9.2 16 reviews
Annapolis, MD
01/01 – 01/02
1079 ﺩ.ﺇ/nighttotal: 33449 ﺩ.ﺇ (31 )

Cute And Close To Downtown! Off Street Parking W/ Short Walk To Academy/stadium

2 2
apartment , Annapolis
This Annapolis Historic District property is less than 1.6km from Peters Cove and the United States Naval Academy, and within a 10-minute walk of Stanton School & Community Centre and the First Baptist Church.
The two-bedroom, two-bathroom house sleeps six guests and boasts a fully equipped kitchen, private balcony, free Wi-Fi, and parking; charcoal grills are available for outdoor cooking.
2026 Commissioning Week Promo: Book 6 Nights, Get The 7th Free - Annapolis, MD
10 3 reviews
Annapolis, MD
21/08 – 24/08
2940 ﺩ.ﺇ/nighttotal: 8820 ﺩ.ﺇ (3 )

2026 Commissioning Week Promo: Book 6 Nights, Get The 7th Free

2 2
apartment , Annapolis
This three-bedroom Annapolis duplex, situated in Eastport, is 2.4 kilometres from the United States Naval Academy, 48 kilometres from Washington, D.C., and 40 kilometres from Baltimore, offering easy access to local eateries and waterfront activities.
The 3-bedroom property, sleeping up to six guests, boasts a private garden with patio and fire pit, two king-sized bedrooms (one with a balcony, the other with a workspace), a fully equipped kitchen including a dishwasher, high-speed Wi-Fi, parking for three cars, and a spa.
Vintage Charm: Annapolis Retreat - Annapolis, MD
9.7 11 reviews
Annapolis, MD
12/11 – 14/11
1535 ﺩ.ﺇ/nighttotal: 3070 ﺩ.ﺇ (2 )

Vintage Charm: Annapolis Retreat

3 2
house , Annapolis
This 1909 Annapolis property is located near Annapolis Harbour, approximately 3 km away, offering easy access to waterfront activities and is around 48 km from Baltimore's attractions.
This three-bedroom house boasts 204 square metres of floor space, comfortably accommodating seven guests with amenities including a fully equipped kitchen, private patio, terrace, garden, and free Wi-Fi and parking.
Parking. Short Uber Ride. Townhouse In Annapolis! 3 Miles From Usna And Downtown - Annapolis, MD
10 1 review
Annapolis, MD
01/01 – 01/02
996 ﺩ.ﺇ/nighttotal: 30876 ﺩ.ﺇ (31 )

Parking. Short Uber Ride. Townhouse In Annapolis! 3 Miles From Usna And Downtown

4 2
apartment , Annapolis
This newly built four-bedroom detached house in Annapolis's Bestgate area offers convenient access to the United States Naval Academy and historic Annapolis, both located 5 kilometres away, with major shopping centres and Anne Arundel Medical Centre also within 2 kilometres.
This spacious 279 square metre property accommodates up to nine guests and features four bathrooms, a unique rooftop bedroom with a wet bar and patio, on-site electric vehicle charging, ample parking including a garage, and is pet-friendly.

Best Annapolis, MD accommodation with a kitchen

Corner House - Cozy Five Star 2 Bedroom Suite. Downtown And Stadium. Parking! - Annapolis, MD
10 21 reviews
Annapolis, MD
01/01 – 01/02
416 ﺩ.ﺇ/nighttotal: 12896 ﺩ.ﺇ (31 )

Corner House - Cozy Five Star 2 Bedroom Suite. Downtown And Stadium. Parking!

2 2
apartment , Annapolis
This Annapolis holiday home is centrally located, within 1.6km of the US Naval Academy and the Annapolis Civil Rights Plaque, and within a 10-minute drive of Asbury United Methodist Church and People's Brewer Hill Cemetery.
The two-bedroom, one-bathroom property sleeps four guests and boasts a fully equipped kitchen, jacuzzi, private patio, and free Wi-Fi, offering a relaxing retreat with easy access to Annapolis's key attractions.
Stay Aboard The S/v My Studio On Annapolis Harbor - Annapolis, MD
9.9 411 reviews
Annapolis, MD
12/11 – 14/11
1134 ﺩ.ﺇ/nighttotal: 2268 ﺩ.ﺇ (2 )

Stay Aboard The S/v My Studio On Annapolis Harbor

2 2
boat , Annapolis
This sailboat is docked in a marina in Annapolis, just a short walk from the historic downtown and the Naval Academy. The marina is well-maintained and offers a peaceful setting, perfect for a relaxing getaway. The boat itself has received excellent ratings for cleanliness, location and user experience.
The vessel features two bedrooms, one bathroom and can accommodate up to four guests. Amenities include a kitchen with a fridge and microwave, air conditioning, a garden, parking, and internet access. Guests can also enjoy private sailing cruises on the Chesapeake Bay (weather permitting) and relax in the cozy cockpit.
Beautiful Condo - Water View Near City Dock - Annapolis, MD
9.7 227 reviews
Annapolis, MD
23/06 – 25/06
1209 ﺩ.ﺇ/nighttotal: 2418 ﺩ.ﺇ (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.
Steps To Usna From Historic Gem W Patio & Parking - Annapolis, MD
9.8 13 reviews
Annapolis, MD
16/07 – 19/07
2602 ﺩ.ﺇ/nighttotal: 7806 ﺩ.ﺇ (3 )

Steps To Usna From Historic Gem W Patio & Parking

3 5
apartment , Annapolis
This fully-renovated historic apartment is situated on Prince George Street in Annapolis's Historic District, just 3 blocks from the U.S. Naval Academy and within walking distance of downtown attractions, St. John's College, and the state capital.
This 3-bedroom, 3-bathroom residence accommodates up to 8 guests and offers a garden with a fire pit and outdoor dining, a double-sided gas fireplace, a gourmet kitchen, a master en-suite with a steam shower, a convertible workspace/bedroom with balcony access, and keyless entry, with dedicated off-site garage parking located a 10-15 minute walk away.
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