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Annapolis, MD place to stay
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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

Eastport Apartment - Annapolis, MD
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.
Lakefront Home With Private Pool, Hot Tub, Outdoor Space, Central Ac, & W/d - Annapolis, MD
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.
Spa Creek Condo | Pool, Deck & Parking - Annapolis, MD
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.
Brick Georgian W Pool, Pet Friendly 1 Mile To All! - Annapolis, MD
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

Fenced + Fire Pit + Coffee Bar 2 Miles From Usna - Annapolis, MD
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.
Gaia House - Annapolis, MD
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.
Walk To Everything Historic Arts District - Annapolis, MD
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.
Annapolis Main Street Modern Apartment - Annapolis, MD
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

Cute Bungalow Blocks To Stadium - Annapolis, MD
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.
Historic Annapolis Home | 2 Blocks To Main St - Annapolis, MD
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.
Cozy, Waterfront, 5br 4ba House W 2 Decks Near Usna & Downtown - Annapolis, MD
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.
Walk To Main Street, City Dock And Usna Gate 1 From Historic Catch 22 With Private Patio - Annapolis, MD
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

5 Br House With Ev Charger Near Downtown Annapolis - Annapolis, MD
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 Gem- Tranquil 4 Br Murray Hill Victorian - Annapolis, MD
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.
Beautiful Condo - Water View Near City Dock - Annapolis, MD
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.
Sleeps 10 | Private Bar & Fenced Yard - Annapolis, MD
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.
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