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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

1st Floor Condo In Annapolis - Annapolis, MD
9.9 163 reviews

1st Floor Condo In Annapolis

apartment, Annapolis
This newly renovated studio flat is situated in Eastport, a quiet neighbourhood directly across Spa Creek from historic Annapolis, within a 1.6 km walk of the city centre and the US Naval Academy.
This pet-free apartment offers a fully equipped kitchen, high-speed Wi-Fi, free onsite parking, a secure building entrance, and a rooftop patio with a seasonal pool, with stunning views of the city.
Waterfront 2-bedroom Condo On Spa Creek - Annapolis, MD
10 15 reviews

Waterfront 2-bedroom Condo On Spa Creek

apartment, Annapolis
This Annapolis Eastport apartment is less than 1.6km from Spa Creek and the United States Naval Academy, and within a 1.6km radius of Annapolis Harbour and the Kunta Kinte Plaque & Alex Haley Memorial.
This two-bedroom, one-bathroom property sleeps six, offering a fully equipped kitchen, private patio, free Wi-Fi, access to a swimming pool, spa, fitness centre, and parking; nearby attractions include the Naval Academy and Annapolis Harbour.
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.

Best family friendly Annapolis, MD lodging

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

Game Days & Family Stays At Dog-friendly Home Near Navy Stadium W Private Fenced-in Yard - Annapolis, MD
10 22 reviews

Game Days & Family Stays At Dog-friendly Home Near Navy Stadium W Private Fenced-in Yard

apartment, Annapolis
This four-bedroom Annapolis holiday home, situated in the Admiral Heights neighbourhood, is 1.1km from the Navy-Marine Corps Memorial Stadium and 3.2km from both the city centre and the United States Naval Academy.
Sleeping nine guests comfortably, this self-catering property boasts a private garden with fire pit, a fully equipped kitchen with stainless steel appliances, two bathrooms, and parking, all within easy reach of Annapolis's key attractions.
Walk To Downtown W Big Yard Dog-friendly & Parking - Annapolis, MD
10 5 reviews

Walk To Downtown W Big Yard Dog-friendly & Parking

apartment, Annapolis
This five-bedroom, two-bathroom flat offers excellent walkability to Annapolis attractions, being 700 metres from the Navy-Marine Corps Memorial Stadium, 1.6 kilometres from Downtown Annapolis shops and restaurants, and 2.9 kilometres from the US Naval Academy.
This dog-friendly residence comfortably accommodates up to 12 guests with a modern HVAC system, high-speed WiFi, three Smart TVs, a sunroom, a fully equipped kitchen with stainless steel appliances, and on-site laundry facilities, plus driveway parking for multiple vehicles.
Cozy 1st Floor King George One Bedroom Apartment Right Across From Usna - Annapolis, MD
9.8 36 reviews

Cozy 1st Floor King George One Bedroom Apartment Right Across From Usna

apartment, Annapolis
This apartment is located in the Historic District, just 1km from the U.S. Naval Academy and within walking distance of John Smith House, William Paca House and Chase Lloyd House. It has received excellent ratings from previous guests.
This one-bedroom flat can accommodate up to four people and features a fully equipped kitchen, a washer and dryer, a comfortable sofa bed, a patio, free Wi-Fi, parking, and a selection of books.
Historic Happy Home Steps From Main Street W Private Yard, Screened-in Porch & Parking - Annapolis, MD
10 36 reviews

Historic Happy Home Steps From Main Street W Private Yard, Screened-in Porch & Parking

apartment, Annapolis
This Annapolis holiday home, a four-bedroom, three-bathroom property, is ideally located one block from Spa Creek and two blocks from Main Street, providing easy access to the US Naval Academy (a 5-block walk), the Maryland State House, and Annapolis's historic district.
The 4-bedroom house sleeps eight guests and features a well-equipped kitchen, a screened porch overlooking a private garden, a dedicated parking space (a 10-minute walk away), two bicycles, Smart TVs, Wi-Fi, and a spa, all within a short distance of shops and restaurants.

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

Walk To Everything Historic Arts District - Annapolis, MD
9.0 12 reviews

Walk To Everything Historic Arts District

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.
Charming Charles -Walkable Downtown Annapolis Home - Annapolis, MD
10 10 reviews

Charming Charles -Walkable Downtown Annapolis Home

apartment, Annapolis
This Annapolis Historic District property is less than 1.6km from the US Naval Academy and Spa Creek, and within 800m of the Banneker-Douglass Museum and Maynard-Burgess House.
This two-bedroom, two-bathroom house sleeps six, features a fully equipped kitchen, private balcony, in-unit laundry, and internet access; nearby attractions include the Naval Academy and various museums.
Exclusive Randall House At Usna Gate 1 W Parking - Annapolis, MD
9.8 90 reviews

Exclusive Randall House At Usna Gate 1 W Parking

apartment, Annapolis
This house is located in Annapolis' Historic District, within walking distance of the U.S. Naval Academy, City Dock, and John Smith House. The surrounding area is steeped in history, with the Kunta Kinte Plaque & Alex Haley Memorial and 14 Fleet Street just a short walk away. This property has excellent user, location, and cleanliness ratings.
The house offers 4 bedrooms and 4 bathrooms, spanning 322 square metres and accommodating up to 11 guests. Enjoy a fully equipped kitchen, a terrace, a garden, a spa, parking, air conditioning, and free Wi-Fi, making it the perfect base for exploring all that Annapolis has to offer.
Historic Row Home 1 Block From Gate 1 At Usna - Annapolis, MD
9.6 5 reviews

Historic Row Home 1 Block From Gate 1 At Usna

house, Annapolis
This Annapolis house, a three-bedroom property, is situated one block from the US Naval Academy's Gate 1, 1.8 kilometres from Annapolis Harbour and 48 kilometres from Baltimore.
Offering 186 square metres of space, this self-catering dwelling sleeps up to 16 guests and boasts a private garden, three bathrooms, free Wi-Fi, and a fully equipped kitchen including a dishwasher.

Best Annapolis, MD accommodations with a kitchen

Step Out To Main Street From A Chic Loft - Annapolis, MD
9.8 1133 reviews

Step Out To Main Street From A Chic Loft

apartment, Annapolis
This Annapolis apartment is located in the heart of the city's bustling downtown area, just a short walk from the waterfront and the Maryland State House. It has received excellent ratings for cleanliness, location and user experience.
The apartment is a comfortable and stylish flat with one bedroom and one bathroom, suitable for up to four guests. The apartment offers a fully equipped kitchen, air conditioning and a unique industrial-chic design with exposed brick walls and hardwood floors, providing a trendy and stylish atmosphere.
Pet-friendly Eastport Yard & Fire Pit - Annapolis, MD
No reviews

Pet-friendly Eastport Yard & Fire Pit

house, Annapolis
This Eastport holiday home is located 2.2 kilometres from Annapolis Harbour and 33.8 kilometres from Baltimore/Washington International Airport.
This spacious two-bedroom, two-bathroom property accommodates up to 10 guests, features a fully equipped kitchen, a garden with an outdoor seating area and fire pit, and offers free on-site private parking.
Beautiful Historic Home Next To City Dock + Usna - Annapolis, MD
10 57 reviews

Beautiful Historic Home Next To City Dock + Usna

apartment, Annapolis
This four-bedroom, one-bathroom apartment in Annapolis city centre is situated just 91 metres from the United States Naval Academy's Gate 1 and City Dock, providing easy walking access to Main Street.
The property, sleeping up to six guests, boasts a large kitchen, a spacious living area with an 80-inch projector screen (Netflix and Apple TV included), and private backyard access; a king-size bed, twin bed, twin bunk beds, and a crib are provided.
Well-appointed 1 Bedroom, 1 Bath In Annap/eastport - Annapolis, MD
9.9 152 reviews

Well-appointed 1 Bedroom, 1 Bath In Annap/eastport

apartment, Annapolis
This one-bedroom flat is situated in Eastport, a lively neighbourhood in Annapolis, just a short walk from the Naval Academy and the downtown waterfront. The apartment enjoys excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The flat is spacious and can comfortably accommodate up to four guests. Amenities include a well-equipped kitchen with a fridge, microwave oven, and dishwasher, a stylish bathroom, a comfortable king-size bed, a 50" TV, and a garden.
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