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

Waterfront Suite With Views Of Annapolis From Prime Eastport Location - Annapolis, MD
9.8 7 reviews

Waterfront Suite With Views Of Annapolis From Prime Eastport Location

apartment, Annapolis
This Eastport condominium provides waterfront accommodation on Spa Creek, situated 800 meters from downtown Annapolis and a 15-minute walk to the U.S. Naval Academy.
This two-bedroom flat accommodates up to five guests and features a private furnished balcony with sweeping views of Spa Creek and historic Annapolis, alongside access to a seasonal waterfront swimming pool and high-speed Wi-Fi.
Captains Quarters Waterfront & Pool - Annapolis, MD
No reviews

Captains Quarters Waterfront & Pool

house, Annapolis
Captains Quarters Waterfront & Pool offers a waterside dwelling in Annapolis, located a short 13-minute walk to Annapolis Harbour and a considerable distance from Baltimore landmarks.
This two-bedroom property, spanning 60 square metres, accommodates up to seven guests and features a private outdoor swimming pool, a fully equipped kitchen, air conditioning, a fireplace, and free private parking.
Tranquil 4br | Pool | Deck | Screened Porch - Annapolis, MD
9.4 7 reviews

Tranquil 4br | Pool | Deck | Screened Porch

apartment, Highland Beach
This Highland Beach flat is located in the Thomas Point district, offering easy access to the coast and local amenities, with popular coastal areas a short journey away. This spacious four-bedroom flat accommodates up to ten guests, featuring air conditioning, a swimming pool, garden, and parking, along with a well-equipped kitchen including a fridge, microwave, and dishwasher.
Waterfront Home W Pool, Pier & Parking Mins To Annapolis - Annapolis, MD
9.6 14 reviews

Waterfront Home W Pool, Pier & Parking Mins To Annapolis

apartment, Arnold
This waterfront property is located in Arnold, just 3.7 kilometres from Severna Park Golf Center and 5 kilometres from Bay Hills Golf Club. It has received excellent user ratings and is ideal for families or groups of friends looking for a comfortable and convenient stay.
The house offers 180 square metres of space, with four bedrooms and three bathrooms, accommodating up to ten guests. Enjoy the outdoor pool, barbecue grills, and a spacious garden, as well as a fully equipped kitchen, a terrace, and a spa.

Best family friendly Annapolis, MD lodging

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

6br 3 Bath Waterfront Home W/ Private Dock & Views - Annapolis, MD
10 1 review

6br 3 Bath Waterfront Home W/ Private Dock & Views

apartment, Mayo
This Edgewater residence offers private waterfront access on Ramsay Lake, with approximately 30 metres of shoreline and a private dock, situated within 1.6 kilometres of Mayo Beach Park and Beverly Triton Beach, and a 32-kilometre drive to downtown Annapolis.
This 144 square metre holiday home accommodates up to 11 guests across 6 bedrooms and 3 bathrooms, featuring a fully equipped kitchen, a dedicated children's area, driveway parking with a Tesla EV charger, a home gym, and on-site stand-up paddleboard use.
Walk To Usna, Main St W Free Off-site Parking - Annapolis, MD
9.8 116 reviews

Walk To Usna, Main St W Free Off-site Parking

apartment, Annapolis
This charming house is situated in Annapolis' Historic District, just a kilometre from The Colonial Players and the U.S. Naval Academy, making it a great base for exploring the city’s rich history and culture. The property has consistently received excellent ratings for location, cleanliness, and overall user experience.
The house has four bedrooms and can accommodate up to eight guests, making it ideal for families or groups of friends. Guests can enjoy the fully equipped kitchen, a comfortable living space, a dedicated library, a terrace, a garden, a spa, and private parking.
Walk To The Naval Academy And Historic Annapolis.  Private Parking At The Home. - Annapolis, MD
10 53 reviews

Walk To The Naval Academy And Historic Annapolis. Private Parking At The Home.

apartment, Annapolis
This three-bedroom, three-bathroom Annapolis holiday home is situated in the Historic District, a mere 0.64 kilometres from the United States Naval Academy and one block from Main Street, five houses from Ego Alley.
Offering off-street parking, a full kitchen, a terrace, and a garden, this property sleeps six guests and is licensed as a vacation rental (STR24-145209), providing easy access to restaurants, pubs, and the Annapolis sailing school.
Family Home On Mayo Peninsula | Deck | Sleeps 10 - Annapolis, MD
10 5 reviews

Family Home On Mayo Peninsula | Deck | Sleeps 10

apartment, Mayo
This Edgewater holiday home in Mayo is situated 4.5km from Triton Beach and within 9.6km of Sand Point Marsh, South River Golf Links, London Town, and the Smithsonian Environmental Research Center.
This 138 square metre property boasts three bedrooms, two bathrooms, sleeps ten guests, and includes a fully equipped kitchen, private patio, garden, free Wi-Fi, 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 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

Cozy 3br Annapolis Sleeps 6 Private Deck, Parking - Annapolis, MD
9.0 1 review

Cozy 3br Annapolis Sleeps 6 Private Deck, Parking

house, Annapolis
This Annapolis property is located 2.2 kilometres from Sparrows Beach and 4.8 kilometres from Annapolis Harbour, offering convenient access to local attractions.
This holiday home, spanning 6 square metres, accommodates up to 10 guests and features air conditioning, free WiFi, a fully equipped kitchen with a dishwasher and oven, a private deck, and free private parking.
Downtown Pinkney House W/parking - Annapolis, MD
9.8 16 reviews

Downtown Pinkney House W/parking

apartment, Annapolis
This Annapolis Historic District property is situated less than a kilometre from Annapolis City Dock and the United States Naval Academy, offering easy access to 14 Fleet Street and The Colonial Players.
The two-bedroom, three-bathroom house sleeps four guests and includes a fully equipped kitchen with dishwasher, in-unit laundry, a balcony, and parking; enjoy nearby attractions and on-site entertainment.
Walk To Downtown Annapolis & Spa Creek From Stunning Craftsman With Game Room, Parking And Backyard - Annapolis, MD
10 21 reviews

Walk 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.
Belle By The Bay Summ - Annapolis, MD
10 4 reviews

Belle By The Bay Summ

apartment, Annapolis
This Annapolis holiday home is situated 0.6km from the Dr Aris T Allen Memorial and 4.7km from the United States Naval Academy, offering easy access to key Annapolis attractions.
Sleeping up to 10 guests, this three-bedroom property boasts a fully equipped kitchen, two bathrooms, a private balcony, garden, parking, and is pet-friendly; nearby amenities include the Wild Bird Center and St John's College.

Best Annapolis, MD accommodations with a kitchen

Beautiful Waterfront Home On The Chesapeake Bay With Private Dock & Beach Access - Annapolis, MD
No reviews

Beautiful Waterfront Home On The Chesapeake Bay With Private Dock & Beach Access

apartment, Highland Beach
This waterside residence in Bay Ridge, Annapolis, offers direct Chesapeake Bay access with a private dock and is situated less than 8 kilometres from historic downtown Annapolis, home to the U.S. Naval Academy.
This 5-bedroom, 3-bathroom maisonette, accommodating up to 10 guests, boasts 645 square metres of living space, featuring renovated interiors, a dedicated home office, a game room with air hockey and foosball, and a hot tub.
Hideaway In The Middle Of Everything Ayc 2+br Apt - Annapolis, MD
9.6 121 reviews

Hideaway In The Middle Of Everything Ayc 2+br Apt

apartment, Annapolis
This Annapolis yacht, situated on Severn Avenue in Eastport, is conveniently located near the Annapolis Yacht Club and Spa Creek Bridge, a 1.5-2.5 km stroll from City Dock and the US Naval Academy.
The two-bedroom, one-bathroom vessel sleeps six adults comfortably, boasting a fully equipped kitchen (fridge, microwave, dishwasher), free Wi-Fi, and ozone sanitization; shared laundry facilities and a private keyed entry are also available, with the option to rent a combined unit with a nearby tiny house.
Charming Rowhome In Downtown Annapolis - Annapolis, MD
9.7 19 reviews

Charming Rowhome In Downtown Annapolis

house, Annapolis
This historic two-bedroom house is situated in the heart of Historic Annapolis, just 200 metres from the Naval Academy, St. John's College, City Dock, and the State House.
This family-friendly holiday let offers accommodation for four guests with a private patio and grill, a full-size washer and dryer, and is equipped with air conditioning and Wi-Fi.
Renovated 3br Near Sandy Point Beach - Annapolis, MD
10 1 review

Renovated 3br Near Sandy Point Beach

house, Arnold
This holiday house is situated in Annapolis, 13 kilometres from Annapolis Harbour and 27 kilometres from Baltimore Washington International Airport.
This expansive property offers 167 square metres of living space with three bedrooms and three bathrooms, accommodating up to 12 guests, and features a fully fitted kitchen, air conditioning, and outdoor seating with a garden.
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