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

Lakefront Home With Private Pool, Hot Tub, Outdoor Space, Central Ac, & W/d - Annapolis, MD
No reviews

Lakefront Home With Private Pool, Hot Tub, Outdoor Space, Central Ac, & W/d

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.
Waterfront 2-bedroom Condo On Spa Creek - Annapolis, MD
10 13 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.
Luxury Annapolis Condo, Fully Remodeled, Rooftop Pool & Marina, Free Parking, 0.3 Mi To Downtown. Perfect For Navy Games, Academy Visits, Or A Waterfront Getaway. - Annapolis, MD
No reviews

Luxury Annapolis Condo, Fully Remodeled, Rooftop Pool & Marina, Free Parking, 0.3 Mi To Downtown. Perfect For Navy Games, Academy Visits, Or A Waterfront Getaway.

apartment, Annapolis
This Eastport condominium provides waterfront access near Annapolis marinas and sailing events, situated within walking distance of downtown Annapolis and its dining options, as well as cultural attractions such as the Annapolis Maritime Museum and The Colonial Players.
This one-bedroom condominium accommodates up to four guests, featuring a fully stocked kitchen, a king bedroom with memory foam beds, a luxurious rainfall shower, and two dedicated parking spaces, complemented by a rooftop pool with harbour views.
Beautiful Basement Apartment In An Upscale Home - Annapolis, MD
9.8 8 reviews

Beautiful Basement Apartment In An Upscale Home

apartment, Arnold
This recently renovated basement flat offers a private entrance within a prestigious waterfront community in Arnold, situated on a 1-hectare wooded plot with direct river beach access and just 100 metres from the Baltimore-Annapolis trail.
This family-friendly accommodation sleeps up to three guests and features air conditioning, a swimming pool, garden, sauna, and parking, with a kitchen equipped with a fridge, freezer, and microwave oven.

Best family friendly Annapolis, MD lodging

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

Perfect Place For Your Family - Annapolis, MD
9.9 44 reviews

Perfect Place For Your Family

house, Arnold
This newly refurbished detached house in Arnold offers a peaceful cul-de-sac location, conveniently situated less than 3.2 kilometres from Sandy Point State Park, a new cycle path, and within 8 kilometres of the U.S. Naval Academy, Navy Stadium, Annapolis City Dock, and the Maryland State House.
This family-friendly property accommodates up to seven guests across three bedrooms, featuring a modern kitchen with a fridge, freezer, microwave, and dishwasher, air conditioning, a garden, and private parking.
Historic + Modern Home | Just Steps To Waterfront - Annapolis, MD
10 49 reviews

Historic + Modern Home | Just Steps To Waterfront

apartment, Annapolis
This Annapolis Fleet Street townhouse, a short walk from City Dock and the United States Naval Academy, offers a prime location in the historic district.
The two-bedroom, one-bathroom apartment sleeps seven, includes a fully equipped kitchen with dishwasher and modern amenities such as Wi-Fi and in-unit laundry, and family-friendly extras are available on request.
Usna Home Steps To Stadium Dog-friendly W Parking - Annapolis, MD
10 77 reviews

Usna Home Steps To Stadium Dog-friendly W Parking

apartment, Annapolis
This apartment is located in West Annapolis, just 1.7 kilometres from the Navy-Marine Corps Memorial Stadium, three blocks from shops and restaurants, and two to three blocks from the city centre. The apartment has excellent guest, location and cleanliness ratings.
This spacious three-bedroom home, with two bathrooms, offers 204 square metres of living space and comfortably accommodates up to 11 guests. The property features a private backyard with a hot tub, fire pit, BBQ grill, and a custom outdoor kitchen, as well as a swimming pool, jacuzzi, garden, spa, tennis court, and parking.
West Annapolis Cottage- 6br  Walk To Navy Stadium - Annapolis, MD
9.9 84 reviews

West Annapolis Cottage- 6br Walk To Navy Stadium

apartment, Annapolis
This West Annapolis holiday home is situated a short distance (approximately 1.6km) from the US Naval Academy football stadium and the shops and restaurants of West Annapolis, with Annapolis Harbour a 5-minute drive away (approximately 3.2km).
Sleeping up to 14 guests in six bedrooms and five bathrooms, the property boasts a fully equipped kitchen, two patios with a gas grill, a games room with ping pong and air hockey, and dedicated parking for two small vehicles.

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

This Thoughtfully Styled Home Overlooks The Bay And Is Perfect For Your Annapolis Escape. - Annapolis, MD
No reviews

This Thoughtfully Styled Home Overlooks The Bay And Is Perfect For Your Annapolis Escape.

apartment, Annapolis
This waterfront property in Annapolis offers direct access to the historic downtown waterfront, sailing, marinas, and Chesapeake Bay views, situated a mere 500 meters from local seafood restaurants, boutiques, and the Naval Academy.
This spacious 550 square meter flat provides accommodation for up to 14 guests across five bedrooms and five bathrooms, featuring a kitchen with a fridge, microwave, and dishwasher, air conditioning, a terrace, and parking.
Historic Row Home | Hot Tub - 1 Block From Gate 1! - Annapolis, MD
9.0 9 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.
Oasis By The Bay - Waterfront Heated Pool Hot Tub! - Annapolis, MD
8.8 6 reviews

Oasis By The Bay - Waterfront Heated Pool Hot Tub!

apartment, Highland Beach
This luxurious six-bedroom Highland Beach waterfront property, situated on a Severn River inlet, offers Chesapeake Bay access and lies 8km from Annapolis and its attractions, including the US Naval Academy.
This 482 square metre holiday home boasts six bathrooms, sleeps eighteen guests, and includes a heated pool (late April-late September), hot tub, multiple patios with stunning Bay views, a rec room with wet bar, and ample parking.
Cute And Close To Downtown! Off Street Parking W/ Short Walk To Academy/stadium - Annapolis, MD
9.2 19 reviews

Cute And Close To Downtown! Off Street Parking W/ Short Walk To Academy/stadium

apartment, Annapolis
This Annapolis Historic District property is less than 1.6km from Peters Cove and the United States Naval Academy, and within a 10-minute walk of Stanton School & Community Centre and the First Baptist Church.
The two-bedroom, two-bathroom house sleeps six guests and boasts a fully equipped kitchen, private balcony, free Wi-Fi, and parking; charcoal grills are available for outdoor cooking.

Best Annapolis, MD accommodations with a kitchen

Golden Anchor Retreat Lux Living! - Annapolis, MD
10 3 reviews

Golden Anchor Retreat Lux Living!

house, Mayo
This Mayo house, situated 14.6 kilometres from Annapolis Harbour and within easy reach of Baltimore and Washington D.C., offers convenient access to major attractions.
This 217 square metre property sleeps 11 guests in three bedrooms, boasting two bathrooms, a fully equipped kitchen with dishwasher, free Wi-Fi, parking, and air conditioning.
Spacious Historic Home Downtown Annapolis Main St. Book For Commissioning Week! - Annapolis, MD
9.2 25 reviews

Spacious Historic Home Downtown Annapolis Main St. Book For Commissioning Week!

apartment, Annapolis
This historic dwelling is located in the heart of Annapolis' Historic District, just a short walk from City Dock, the US Naval Academy, and Main Street, offering easy access to the city's attractions and amenities. The apartment has received excellent user ratings, reflecting its high standard of comfort and service.
The spacious home features six bedrooms, five bathrooms, and can accommodate up to 16 guests, spanning a generous 353 square metres. Amenities include a fully equipped kitchen, a spa, air conditioning, and a private patio, offering a comfortable and enjoyable stay for families and groups.
Boutique Brick Beauty - Annapolis, MD
9.9 18 reviews

Boutique Brick Beauty

apartment, Annapolis
This two-bedroom, one-bathroom apartment in Annapolis's historic Eastport district is located a short walk (less than 2km) from the downtown area, the United States Naval Academy, and the waterfront, with the Navy-Marine Corps Memorial Stadium under 5km away.
The self-catering property offers two off-street parking spaces, sleeps four guests, and features a fully equipped kitchen, Wi-Fi, Smart TVs, and a garden, perfect for families or groups visiting Annapolis.
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.
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