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Annapolis, MD place to stay
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1103 Lodgings in Annapolis, MD

Best Annapolis, MD lodging with a pool

Among the 1103 accommodations in Annapolis, MD, here are the 4 best ones with a pool

The Usna Getaway! - Annapolis, MD
9.8 76 reviews

The Usna Getaway!

apartment, Annapolis
This Annapolis apartment, less than 0.8km from the United States Naval Academy and Annapolis city centre, and under 100 feet from Spa Creek, offers superb waterfront access.
Sleeping six guests, this one-bedroom condo boasts a California king bed, queen Murphy bed, and queen pull-out sofa, plus a fully equipped kitchen including a dishwasher, and access to a rooftop swimming pool with city views; nearby restaurants are within easy walking distance.
South River Beach Front House - Annapolis, MD
9.7 43 reviews

South River Beach Front House

apartment, Mayo
This Mayo waterfront property, situated on the South River, offers a stunning location just 3m from the water's edge and close to community tennis and basketball courts.
Sleeping up to 10 guests, this recently renovated (2024) three-bedroom, two-bathroom house boasts a private 38m pier, heated riverside pool, sunroom, and spacious living area with fireplace; enjoy crabbing, fishing, and exploring the local area.
Prime Eastport Location - Waterfront Condo W Pool & Parking - Annapolis, MD
10 32 reviews

Prime Eastport Location - Waterfront Condo W Pool & Parking

apartment, Annapolis
This Annapolis apartment, situated in Eastport, is less than 2km from Spa Creek and the United States Naval Academy, offering easy access to the Kunta Kinte-Alex Haley Memorial and Maynard-Burgess House within a 15-minute drive.
The three-bedroom, two-bathroom property sleeps seven guests and includes a full kitchen, terrace, free Wi-Fi, on-site parking, and swimming pool access; nearby attractions include the Naval Academy and the Chesapeake Bay.
Spacious Luxe Usna Home - Pool, Hot Tub, Grill - Annapolis, MD
9.8 91 reviews

Spacious Luxe Usna Home - Pool, Hot Tub, Grill

apartment, Annapolis
This five-bedroom Annapolis house, a short walk from the United States Naval Academy and Main and West Streets' restaurants, offers convenient access to Annapolis's key attractions.
Sleeping fourteen guests, this spacious three-storey property boasts five bathrooms, a fully equipped kitchen including a dishwasher, and a gas grill; nearby parking is available.

Best family friendly Annapolis, MD lodging

Among the 1103 accommodations in Annapolis, MD, here are the 4 best for families

The Sail Loft - Annapolis, MD
10 41 reviews

The Sail Loft

apartment, Annapolis
This three-bedroom Annapolis apartment, less than 0.16 km from Spa Creek and a 10-minute walk from Annapolis's city centre, offers easy access to all major attractions.
Sleeping eight guests comfortably, the property boasts a huge balcony overlooking Spa Creek, a fully equipped kitchen including a dishwasher, two bathrooms, and access to a shared garden; ideal for families exploring this historic Maryland city.
Adorable Home Steps From Navy Stadium! - Annapolis, MD
No reviews

Adorable Home Steps From Navy Stadium!

apartment, Annapolis
This four-bedroom flat in West Annapolis offers immediate access to Annapolis events, situated a mere block from Navy Stadium and within 1.6 kilometres of downtown Annapolis's shops and eateries.
This spacious accommodation for up to eleven guests boasts a deck with a grill, a brick patio with a fire pit, a downstairs wet bar, and two off-street parking spaces, making it ideal for groups attending boat shows or reunions.
Stylish + Fresh Bungalow 2 Blocks From N-mc Stadium - Annapolis, MD
No reviews

Stylish + Fresh Bungalow 2 Blocks From N-mc Stadium

house, Annapolis
Vacation house to rent. You will be located in Annapolis.
Services and facilities: a fridge, air conditioning and an iron.
Stadium-side Annapolis | Chef Kitchen | Sleeps 10 - Annapolis, MD
9.9 24 reviews

Stadium-side Annapolis | Chef Kitchen | Sleeps 10

apartment, Annapolis
This 1.5-storey townhouse in Annapolis is situated a few minutes' walk from the stadium, offering convenient access to local events.
This 214 square metre residence accommodates up to 10 guests, featuring a chef's kitchen with GE Café appliances, a spa-like master bathroom, and a fully finished basement, with keypad entry for secure access.

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.

Popular destinations

Best Annapolis, MD accommodations with a balcony

Downtown Annapolis Charming 2 Bdr Townhome - Annapolis, MD
No reviews

Downtown Annapolis Charming 2 Bdr Townhome

apartment, Annapolis
This newly renovated 2-bedroom flat in Annapolis's Historic District is just a short walk from Annapolis Harbour and Ego Alley.
This residence accommodates up to five guests and features a well-equipped kitchen, air conditioning, a private garden, and in-unit laundry facilities.
Spacious 5 Br House - 5 Min Walk To N-mc Stadium! - Annapolis, MD
9.8 6 reviews

Spacious 5 Br House - 5 Min Walk To N-mc Stadium!

apartment, Annapolis
This Annapolis holiday home, situated in the Germantown neighbourhood, is located two blocks from the Navy-Marine Corps Memorial Stadium and an eight-minute drive (approximately 6.4km) from the United States Naval Academy and Annapolis city centre.
This spacious property boasts 242 square metres of floor area, offering five bedrooms (three main bedrooms and two bunk rooms in the basement), accommodating up to 15 guests and featuring amenities such as a jacuzzi bath, foosball table, and a fully enclosed garden.
Pet Friendly Park Free & Walk To Usna Stadium - Annapolis, MD
No reviews

Pet Friendly Park Free & Walk To Usna Stadium

house, Annapolis
This pet-friendly holiday home offers free private parking and is situated just over 3.2 kilometres from Annapolis Harbour and within easy reach of the USNA Stadium.
This spacious 223 square metre property accommodates up to 16 guests across four bedrooms, featuring a well-equipped kitchen, a fitness room, a terrace with city views, and a garden.
Downtown Furnished Apartment - Walking Distance To Restaurants - Annapolis, MD
10 11 reviews

Downtown Furnished Apartment - Walking Distance To Restaurants

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.

Best Annapolis, MD accommodations with a kitchen

Stadium-side Annapolis | Chef Kitchen | Sleeps 10 - Annapolis, MD
9.8 11 reviews

Stadium-side Annapolis | Chef Kitchen | Sleeps 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.
Anchors Away - Annapolis, MD
9.7 144 reviews

Anchors Away

apartment, Annapolis
This one-bedroom flat is located in Eastport, just 1 kilometre from the Annapolis Maritime Museum and the US Naval Academy, and within 1.6 kilometres of Spa Creek and the Kunta Kinte Plaque & Alex Haley Memorial. The property has received excellent ratings for its location, cleanliness and overall experience.
The flat is equipped with a fully equipped kitchen, a washing machine and dryer, free Wi-Fi, and a smart TV. Guests can enjoy the outdoor barbecue facilities, and the property is smoke-free.
Bungalow Basement In Annapolis - Annapolis, MD
9.8 51 reviews

Bungalow Basement In Annapolis

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.
Spacious Luxe Usna Home - Pool, Hot Tub, Grill - Annapolis, MD
9.4 30 reviews

Spacious Luxe Usna Home - Pool, Hot Tub, Grill

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.
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