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 Eastport Condo W Pool & Parking - Annapolis, MD
9.7 12 reviews

Waterfront Eastport Condo W Pool & Parking

apartment, Annapolis
This Annapolis apartment, situated in Eastport, is less than 1km from Annapolis city centre and 1.3km from the United States Naval Academy.
Sleeping up to seven guests, this two-bedroom, two-bathroom flat boasts a king-size suite, twin guest room with daybeds, queen sofa bed, rooftop pool (seasonal), and stunning Spa Creek and downtown views.
Spa Creek Waterfront | Pool & Parking - Annapolis, MD
10 19 reviews

Spa Creek Waterfront | Pool & Parking

apartment, Annapolis
This Eastport condo offers waterfront living on Spa Creek, a mere 800 meters' walk to Downtown Annapolis and the US Naval Academy.
This two-bedroom flat accommodates up to four guests and features a communal swimming pool (seasonal), a fitness centre, and complimentary parking for two cars, with a covered deck providing water views.
Spacious Luxe Usna Home - Pool, Hot Tub, Grill - Annapolis, MD
9.8 90 reviews

Spacious Luxe Usna Home - Pool, Hot Tub, Grill

house, 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.
Beautiful Condo - Water View Near City Dock - Annapolis, MD
9.7 241 reviews

Beautiful Condo - Water View Near City Dock

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.

Best family friendly Annapolis, MD lodging

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

Recently Renovated Annapolis Home - Conveniently Located - Annapolis, MD
10 79 reviews

Recently Renovated Annapolis Home - Conveniently Located

apartment, Annapolis
This four-bedroom apartment is located in the heart of Annapolis, within easy walking distance of the US Naval Academy and the Navy-Marine Corps Memorial Stadium. It has consistently received excellent reviews from guests, who appreciate its comfortable and spacious accommodation.
The apartment has three bathrooms and can comfortably accommodate up to eight guests. It comes equipped with modern amenities, including a fully fitted kitchen, a separate TV/play room, and a private garden with a patio and front porch.
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.
Historic Row Home | Hot Tub - 1 Block From Gate 1! - Annapolis, MD
9.0 10 reviews

Historic Row Home | Hot Tub - 1 Block From Gate 1!

apartment, Annapolis
This Annapolis holiday home is situated in the Historic District, a short distance from Annapolis City Dock.
This three-bedroom, two-and-a-half-bathroom apartment offers 186 square metres of living space, complete with a fully equipped kitchen, in-unit laundry, private balcony, and access to an outdoor grill; nearby attractions include Jonas Green State Park and Hammond-Harwood House.
Stunning View 3br Waterfront Home | Screened Porch - Annapolis, MD
8.0 5 reviews

Stunning View 3br Waterfront Home | Screened Porch

apartment, Highland Beach
This Highland Beach flat offers a peaceful beachfront setting, with direct access to the sand and a 10-minute drive to Delray Beach's Atlantic Avenue.
This family-friendly three-bedroom, three-bathroom property sleeps up to ten guests and includes air conditioning, a kitchen with a fridge, microwave, and dishwasher, as well as garden access 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 history! You have to see the US Naval Academy, it's a sight to behold. The State House is another must-see, it's the oldest state capitol building still in use in the US. And don't forget to stroll around the historic district, with its charming cobblestone streets and beautiful 18th-century architecture.
  • 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.

  • Which cultural festivals and seasonal events should visitors attend in Annapolis, MD?

    There's always something going on in Annapolis! The Annapolis Maritime Museum's 'Waterfront Festival' in June is a big one, with live music and boat races. In October, the 'Annapolis Fall Festival' is a real treat, with arts and crafts, food stalls, and plenty of entertainment. And don't miss the 'Christmas in Annapolis' festivities in December, with lights, decorations, and festive cheer.
  • What are the best accommodations with a pool in Annapolis, MD?

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

    Annapolis is quite walkable, especially in the downtown area. You can also easily get around by using the free Circulator bus service. If you need to travel further afield, the Annapolis Area Regional Transportation (AART) provides bus services to surrounding areas. And of course, you can always hire a taxi or ride-sharing service.
  • What are the best accommodations with a jacuzzi in Annapolis, MD?

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

    Annapolis is a great place for outdoor activities. You can take a boat tour of the Chesapeake Bay, go kayaking or paddleboarding on the Severn River, or explore the scenic trails at Quiet Waters Park. If you're feeling adventurous, you can even go fishing or crabbing from the docks.
  • What are the best accommodations for families and kids in Annapolis, MD?

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

    Annapolis has a wide range of accommodation options, from budget-friendly motels to luxurious hotels. There are also plenty of charming bed and breakfasts and vacation rentals available. You can find something to suit every taste and budget.
  • What are the best pet friendly accommodations in Annapolis, MD?

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

    The best time to visit Annapolis really depends on what you're looking for. Spring and autumn are lovely, with mild temperatures and fewer crowds. Summer is great for outdoor activities, but it can get hot and humid. Winter can be chilly, but it's a beautiful time to see the city decked out for the holidays.
  • 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.

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

    You have to try the fresh seafood in Annapolis! The Chesapeake Bay is famous for its blue crabs, so be sure to try them steamed or in a crab cake. And don't forget to sample the local oysters, they're a real delicacy. For a unique experience, try dining at one of the many waterfront restaurants with stunning views of the harbour.
  • In which part of Annapolis, MD should you consider renting accommodation?

    The historic district is a popular choice for accommodation, as it's close to all the main attractions. If you're looking for a more peaceful stay, you could consider renting a property in Eastport, which is a charming waterfront community. And if you're on a budget, you might want to look for accommodation in the outskirts of Annapolis.

Popular destinations

Best Annapolis, MD accommodations with a balcony

Historic Annapolis Home  Walk To Downtown  3br - Annapolis, MD
No reviews

Historic Annapolis Home Walk To Downtown 3br

apartment, Annapolis
This property is located in the historic West Street district of Annapolis, a 5-minute walk from Main Street, the waterfront, and the Naval Academy.
This 170 square metre flat accommodates up to 8 guests and features a fully equipped kitchen, a private garden with a deck, and a dedicated workspace, with high-speed WiFi available.
Cute Bungalow Blocks To Stadium - Annapolis, MD
9.4 11 reviews

Cute Bungalow Blocks To Stadium

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.
Your Annapolis Waterfront Retreat For A Weekend Or Any-day Getaway!<br>great Lodging For Plebe Parent's Weekend - And All Your Usna Activities. - Annapolis, MD
10 257 reviews

Your Annapolis Waterfront Retreat For A Weekend Or Any-day Getaway!<br>great Lodging For Plebe Parent's Weekend - And All Your Usna Activities.

cottage, Annapolis
This charming waterfront cottage is located in West Annapolis, just a short walk from the US Naval Academy and a 1.5-mile stroll from the Annapolis City Dock. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
This delightful cottage offers 65 square metres of space and can accommodate up to four guests. The property boasts a fully equipped kitchen, a screened-in porch, a private waterfront backyard with a fire pit, and a private dock with access to Weems Creek, making it ideal for relaxing and enjoying the beautiful surroundings.
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

Bungalow Basement In Annapolis - Annapolis, MD
9.8 50 reviews

Bungalow Basement In Annapolis

house, 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.
Modern Eastport Getaway, Near Historic Annapolis - Annapolis, MD
9.6 24 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.
Eastport Cottage .5 Mi From Downtown Annapolis - Annapolis, MD
10 62 reviews

Eastport Cottage .5 Mi From Downtown Annapolis

apartment, Annapolis
This two-bedroom house is located in Eastport, Annapolis, within 1.6km of Spa Creek and the U.S. Naval Academy. The property boasts excellent user, location, and cleanliness ratings, making it an ideal choice for travellers seeking a comfortable and convenient stay.
The house features a fully equipped kitchen, a private patio, and a garden. Guests can enjoy the warm Annapolis weather with barbecue grills and benefit from free Wi-Fi and air conditioning.
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.
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