Places to stay in Annapolis, MD

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Annapolis, MD place to stay
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1103 Best places to stay in Annapolis, MD

Best Annapolis, MD lodgings with a pool

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

Spa Creek Waterfront Pool & Parking - Annapolis, MD
10 1 review

Spa Creek Waterfront Pool & Parking

house, Annapolis
This Annapolis apartment offers direct waterfront access on Spa Creek, placing it a 13-minute walk from Annapolis Harbour and 42 kilometres from Baltimore's Inner Harbour.
This two-bedroom, one-bathroom apartment, accommodating up to seven guests, features a fully equipped kitchen, air conditioning, a swimming pool, fitness centre, and private parking, with a floor area of 60 square metres.
Modern Eastport Getaway, Near Historic Annapolis - Annapolis, MD
9.7 21 reviews

Modern Eastport Getaway, Near Historic Annapolis

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.
"Woodland Studio" Terrace Apartment - Annapolis, MD
No reviews

"Woodland Studio" Terrace Apartment

apartment, Annapolis
This studio apartment is located in the tranquil woodland of West Annapolis, offering a peaceful retreat just a short distance from the historic Annapolis city centre, with convenient access to its attractions without the usual urban congestion.
This self-contained unit accommodates up to three guests, featuring a queen bed and an optional inflatable twin, a well-equipped kitchen with a dishwasher, air conditioning, and access to a communal swimming pool and fitness centre, all accessible via a private entrance.
Waterfront Oasis Of Annapolis Star - Annapolis, MD
10 85 reviews

Waterfront Oasis Of Annapolis Star

apartment, Arnold
This flat is situated in Annapolis, just a short distance from the Maryland World War II Memorial, Jonas Green State Park, and the Naval Health Clinic. It has received excellent reviews from previous guests.
The apartment is well-equipped and includes a kitchen with a fridge, microwave, and dishwasher. It also offers a range of amenities, such as a private pool, a fireplace, a terrace, and free Wi-Fi.

Best family friendly Annapolis, MD lodging

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

Perfect Home For Annapolis Boat Shows! - Annapolis, MD
10 4 reviews

Perfect Home For Annapolis Boat Shows!

apartment, Annapolis
This four-bedroom apartment is situated in a quiet residential area, just 0.4km from the stadium and 1.6km from the historic downtown Annapolis and the U.S. Naval Academy. The apartment has consistently received excellent ratings for location, cleanliness, and overall experience.
The apartment is spacious and comfortable, accommodating up to 10 guests. It features a gourmet kitchen, a private garden, and a large deck, perfect for enjoying the fresh air. You can also take advantage of the nearby attractions, including nightlife, family-friendly activities, art and culture, and exceptional views.
Historic Home In Annapolis - Annapolis, MD
9.9 51 reviews

Historic Home In Annapolis

apartment, Annapolis
This three-bedroom, two-bathroom house, situated in Annapolis's Historic District on a prime street linked to Francis Scott Key, offers easy walking access to Annapolis's many historical sites.
Sleeping six, this family-friendly property boasts a chef's kitchen with high-end appliances, a garden with fire pit, multiple Smart TVs, in-unit laundry, and even a portable bassinet and playard.
Beachfront Home Minutes To Downtown Annapolis Dogs Ok - Annapolis, MD
9.8 43 reviews

Beachfront Home Minutes To Downtown Annapolis Dogs Ok

cottage, Annapolis
This charming cottage is located just 4 km from downtown Annapolis and 4.5 km from the US Naval Academy, offering a peaceful escape close to the city's attractions. It has received excellent guest reviews, making it a popular choice for travellers seeking a comfortable and well-equipped stay.
The cottage comfortably sleeps 8 guests and features 3 bedrooms and 2 bathrooms, providing ample space for families or groups. Enjoy the private beach with direct bay access, a gourmet kitchen, a spacious garden, and a range of amenities including paddle boards, life jackets, and a barbecue grill.
Stay Mins From Annapolis In Luxury Waterfront Home On Deep Water W Private Pier & Gourmet Kitchen - Annapolis, MD
9.0 12 reviews

Stay Mins From Annapolis In Luxury Waterfront Home On Deep Water W Private Pier & Gourmet Kitchen

apartment, Crownsville
This luxurious four-bedroom, four-bathroom waterfront property in Crownsville, Maryland, boasts direct Severn River access with a private pier, situated approximately 11 kilometres from Annapolis city centre and 39 kilometres from Baltimore.
The spacious holiday home, sleeping up to twelve guests, offers a gourmet kitchen, private garden with a patio, multiple Smart TVs, high-speed internet, and easy access to kayaking, paddleboarding, and canoeing on the river, plus nearby attractions including the Eisenhower Golf Course and Arundel Mills Mall.

Frequently asked questions about accommodations in Annapolis, MD

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

    Annapolis is packed with historical sites! You've got the iconic Maryland State House, the oldest state capitol still in use in the US, and the US Naval Academy, where you can wander around and maybe catch a midshipman parade. Then there's the Annapolis Maritime Museum, which is great for learning about the city's maritime history, and of course, the charming shops and restaurants along the harbour.
  • 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 Modern Apartment Over The Heart Of Main Street are the most popular ones.

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

    Annapolis is a very walkable city, so you can easily explore the downtown area on foot. If you're planning to venture further afield, the Annapolis Circulator bus system is a great option. It runs on a loop, connecting key areas like the harbour, the Naval Academy, and the historic district. Taxis are also readily available, and you can even rent a bike to explore the city at your own pace.
  • What are the best accommodations with a pool in Annapolis, MD?

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

    Annapolis is surrounded by beautiful waterways, making it a great spot for water sports. You can rent a kayak or canoe and explore the harbour, go sailing in the Chesapeake Bay, or even take a scenic cruise. For those who prefer to stay on land, the scenic trails around the city are perfect for hiking, biking, and birdwatching. The Anne Arundel County Recreation and Parks Department offers a variety of outdoor activities, including fishing, boating, and camping.
  • What are the best accommodations with a jacuzzi in Annapolis, MD?

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

    You've got plenty of options when it comes to accommodation in Annapolis. There are charming bed and breakfasts tucked away in historic neighbourhoods, modern hotels near the harbour, and even some waterfront resorts. If you're looking for something more budget-friendly, there are also some motels and vacation rentals scattered around the city.
  • What are the best accommodations for families and kids in Annapolis, MD?

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

    The best time to visit Annapolis is during the spring or autumn, when the weather is mild and the crowds are smaller. The summer months can be hot and humid, but they're perfect for enjoying the waterfront activities. If you're a fan of winter festivities, you can visit during the holiday season and experience the city's festive atmosphere.
  • What are the best pet friendly accommodations in Annapolis, MD?

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

    You absolutely must try the Chesapeake Bay blue crabs, steamed and served with Old Bay seasoning. They're a local delicacy! For a more casual dining experience, head to one of the many seafood restaurants along the harbour. You can find everything from fresh oysters and clams to delicious crab cakes. Don't forget to try the local craft beers and wines, too.
  • What are the best accommodations with parking in Annapolis, MD?

    Graduate By Hilton Annapolis, Springhill Suites By Marriott Annapolis and Historic Inns Of Annapolis are the best accommodations with parking in Annapolis, MD.

  • In which part of Annapolis, MD should you consider renting accommodation?

    If you want to be in the heart of the action, staying in the downtown area near the harbour is a great choice. You'll be within walking distance of all the major attractions, restaurants, and shops. For a more peaceful and secluded experience, you can consider renting a room in a bed and breakfast in one of the historic neighbourhoods. If you're travelling with a family, you might prefer a hotel or resort near the waterfront.

Popular destinations

Best Annapolis, MD accommodations with a balcony

Chapel Gate 3br Steps To City Dock & Naval Academy - Annapolis, MD
No reviews

Chapel Gate 3br Steps To City Dock & Naval Academy

apartment, Annapolis
This top-floor, three-bedroom flat is located in Annapolis's Historic District, a few blocks from the U.S. Naval Academy's Gate 3 and City Dock, placing you within easy reach of the Hammond-Harwood House and Thurgood Marshall Memorial.
This 111 square metre residence accommodates up to six guests with three bedrooms, a fully equipped kitchen, in-unit laundry, and a Roku TV, whilst its proximity to the Tose Family Tennis Centre and Annapolis Harbour offers ample recreational opportunities, and pets are welcome for an additional fee.
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.
Parking. Short Uber Ride. Townhouse In Annapolis! 3 Miles From Usna And Downtown - Annapolis, MD
10 1 review

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

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.
Steps To Downtown Annapolis & Spa Creek From Stunning Craftsman With Game Room, Parking And Backyard - Annapolis, MD
10 21 reviews

Steps To Downtown Annapolis & Spa Creek From Stunning Craftsman With Game Room, Parking And Backyard

apartment, Annapolis
This charming lighthouse is situated in Eastport, Annapolis, a short walk from downtown Annapolis (1.1 km), the US Naval Academy (1.4 km), and Fourth Street shops and restaurants (0.3 km). This property enjoys excellent user ratings and offers a comfortable and convenient stay.
The lighthouse provides 4 bedrooms and 4 bathrooms, accommodating up to 12 guests. Guests can enjoy a range of amenities and activities, including a gourmet kitchen, a recreation room, multiple outdoor spaces, and family-friendly features.

Best Annapolis, MD accommodations with a kitchen

Coastal Edgewater Home W/ Private Hot Tub! - Annapolis, MD
No reviews

Coastal Edgewater Home W/ Private Hot Tub!

house, Mayo
This spacious Mayo holiday home is located 35km from Annapolis Harbour and 40km from Baltimore-Washington International Thurgood Marshall Airport.
The 218 square metre property boasts five bedrooms sleeping up to 17 guests, a fully equipped kitchen with dishwasher, air conditioning, a jacuzzi, free Wi-Fi, and parking; nearby attractions include Annapolis Harbour for water activities.
Renovated Cape Cod Private Nest In West Annapolis - Annapolis, MD
9.9 59 reviews

Renovated Cape Cod Private Nest In West Annapolis

apartment, Annapolis
This West Annapolis cottage, situated 0.8km from Route 50 and 2.4km from Historic Annapolis, offers easy access to the US Naval Academy, St John's College, and City Dock.
The 84 square metre self-catering property sleeps four guests in one bedroom and one bathroom, boasting a renovated kitchen, screened-in deck, and keyless entry; nearby attractions include the Navy Stadium.
Charming Eastport Capecod - Annapolis, MD
10 77 reviews

Charming Eastport Capecod

apartment, Annapolis
This four-bedroom home in Eastport is located just 1.6 kilometres from downtown Annapolis, City Dock, and shops, offering easy access to the city's main attractions. The area is popular for its local pubs and restaurants, making it an ideal location for those seeking a vibrant and convenient stay. The property has consistently received excellent ratings for its cleanliness, location, and user experience.
The property boasts a spacious open-plan kitchen and living room, perfect for entertaining up to 10 guests. Guests can enjoy the large private backyard with a patio, fire pit, and grill, perfect for al fresco dining and relaxation.
Great Location On Spa Creek - Annapolis, MD
9.7 236 reviews

Great Location On Spa Creek

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.
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