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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
24/07 – 29/07
916 ﺩ.ﺇ/nighttotal: 4580 ﺩ.ﺇ (5 )

Semper Fi Condo

1 3
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.
Spa Creek Condo | Pool, Deck & Parking - Annapolis, MD
10 5 reviews
Annapolis, MD
17/09 – 22/09
1446 ﺩ.ﺇ/nighttotal: 7230 ﺩ.ﺇ (5 )

Spa Creek Condo | Pool, Deck & Parking

1 1
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.
Stadium-side Annapolis | Chef Kitchen | Sleeps 10 - Annapolis, MD
10 10 reviews
Annapolis, MD
01/01 – 01/02
1216 ﺩ.ﺇ/nighttotal: 37696 ﺩ.ﺇ (31 )

Stadium-side Annapolis | Chef Kitchen | Sleeps 10

3 2
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.
The Retreat @ Back Creek - Annapolis, MD
9.9 38 reviews
Annapolis, MD
06/08 – 10/08
6382 ﺩ.ﺇ/nighttotal: 25528 ﺩ.ﺇ (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.

Best family friendly Annapolis, MD lodging

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

Walk To Everything Historic Arts District - Annapolis, MD
8.8 11 reviews
Annapolis, MD
06/11 – 08/11
1510 ﺩ.ﺇ/nighttotal: 3020 ﺩ.ﺇ (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.
Pristine Downtown 1-bedroom Steps From State House - Annapolis, MD
10 40 reviews
Annapolis, MD
24/07 – 29/07
1113 ﺩ.ﺇ/nighttotal: 5565 ﺩ.ﺇ (5 )

Pristine Downtown 1-bedroom Steps From State House

1 3
apartment , Annapolis
This Annapolis Historic District flat is situated a short walk from the United States Naval Academy and East Street's shops and restaurants, offering easy access to attractions like The Colonial Players and 48 Fleet Street.
The 37-square-metre (approximately 398 square feet) self-catering property sleeps four guests and includes two bedrooms, one bathroom, a fully equipped kitchen, in-unit laundry, free Wi-Fi, and on-site parking.
Secluded Cozy Cottage In Historic Downtown - Annapolis, MD
9.6 20 reviews
Annapolis, MD
17/09 – 22/09
2416 ﺩ.ﺇ/nighttotal: 12080 ﺩ.ﺇ (5 )

Secluded Cozy Cottage In Historic Downtown

2 1
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 Getaway - 45 Steps To Downtown And 150 Steps To Usna! - Annapolis, MD
9.9 112 reviews
Annapolis, MD
24/07 – 29/07
2692 ﺩ.ﺇ/nighttotal: 13460 ﺩ.ﺇ (5 )

Historic Annapolis Getaway - 45 Steps To Downtown And 150 Steps To Usna!

4 3
apartment , Annapolis
This charming house is located in the heart of downtown Annapolis, just a short walk from City Dock, restaurants, and the US Naval Academy. The property enjoys excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The spacious house has four bedrooms and three bathrooms, comfortably accommodating up to eight guests. The fully equipped kitchen includes a fridge, freezer, microwave oven, and dishwasher, while other amenities include air conditioning, a garden, a spa, and parking.

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

Downtown Furnished Apartment - Walking Distance To Restaurants - Annapolis, MD
10 10 reviews
Annapolis, MD
25/06 – 28/06
1383 ﺩ.ﺇ/nighttotal: 4149 ﺩ.ﺇ (3 )

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.
New! Private, Family-friendly Home Near Usna - Annapolis, MD
Annapolis, MD
25/06 – 28/06
2500 ﺩ.ﺇ/nighttotal: 7500 ﺩ.ﺇ (3 )

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.
Luxury Rooftop Pool & Dock Steps To Downtown - Annapolis, MD
10 1 review
Annapolis, MD
11/09 – 19/09
2021 ﺩ.ﺇ/nighttotal: 16168 ﺩ.ﺇ (8 )

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.
Coastal Modern Retreat | Large Group Getaway On 2 Acres - Annapolis, MD
Annapolis, MD
06/08 – 10/08
6800 ﺩ.ﺇ/nighttotal: 27200 ﺩ.ﺇ (4 )

Coastal Modern Retreat | Large Group Getaway On 2 Acres

6 10
apartment , Arnold
This 6-bedroom, 4-bathroom residence in Arnold, Maryland, offers a secluded 1.8-acre setting with sunset views, conveniently located a short drive from local beaches, restaurants, and nightlife, as well as golf at Severna Park Golf Center and Bay Hills Golf Club.
This pet-friendly holiday home features two kitchens, two living areas, and a deck with a BBQ, providing ample space for up to 15 guests, with proximity to attractions such as Helen Avalynne Tawes Garden and French Soldiers Monument, and within driving distance of events at Alumni Hall and Navy-Marine Corps Memorial Stadium.

Best Annapolis, MD accommodation with a kitchen

Gaia House - Annapolis, MD
9.9 21 reviews
Annapolis, MD
27/06 – 29/06
839 ﺩ.ﺇ/nighttotal: 1678 ﺩ.ﺇ (2 )

Gaia House

1 2
apartment , Annapolis
This Annapolis house, ideally located for exploring the city's attractions, offers easy access to Annapolis's historic district.
The two-bedroom property sleeps four, features a full kitchen with fridge, freezer, and microwave, and includes parking, Wi-Fi, and air conditioning.
Main Street Overlook - Annapolis, MD
10 7 reviews
Annapolis, MD
04/07 – 05/07
2623 ﺩ.ﺇ/nightfor 1 night

Main Street Overlook

1 2
apartment , Annapolis
This two-bedroom, one-bathroom apartment is situated on Main Street in Annapolis' historic downtown, offering easy access to shops, restaurants, and the US Naval Academy (distance unspecified).
The self-catering flat sleeps four guests and features a full kitchen, air conditioning, and internet access; its Main Street location provides excellent people-watching opportunities.
New Luxury Townhome Near Downtown Annapolis With Multiple Ensuite Bedrooms And Parking - Annapolis, MD
Annapolis, MD
06/08 – 10/08
4854 ﺩ.ﺇ/nighttotal: 19416 ﺩ.ﺇ (4 )

New Luxury Townhome Near Downtown Annapolis With Multiple Ensuite Bedrooms And Parking

4 10
apartment , Annapolis
This brand-new, four-level farmhouse-style townhome is located just 3.2 kilometres from the U.S. Naval Academy and 2 kilometres from the Navy-Marine Corps Memorial Stadium, offering a convenient base for exploring Annapolis.
This spacious 210 square metre residence accommodates up to 12 guests with five bedrooms, four en-suite bathrooms, a gourmet kitchen, and a terrace, while being dog-friendly and offering ample parking.
West Annapolis Cottage- 6br  Walk To Navy Stadium - Annapolis, MD
9.9 83 reviews
Annapolis, MD
06/08 – 10/08
5158 ﺩ.ﺇ/nighttotal: 20632 ﺩ.ﺇ (4 )

West Annapolis Cottage- 6br Walk To Navy Stadium

1 10
apartment , Annapolis
This West Annapolis holiday home is situated a short distance (approximately 1.6km) from the US Naval Academy football stadium and the shops and restaurants of West Annapolis, with Annapolis Harbour a 5-minute drive away (approximately 3.2km).
Sleeping up to 14 guests in six bedrooms and five bathrooms, the property boasts a fully equipped kitchen, two patios with a gas grill, a games room with ping pong and air hockey, and dedicated parking for two small vehicles.
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