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

Luxury Rooftop Pool & Dock Steps To Downtown - Annapolis, MD
10 1 review

Luxury Rooftop Pool & Dock Steps To Downtown

house, Annapolis
This luxury condominium in Annapolis is located a 13-minute walk from Annapolis Harbour and 41.8 kilometres from Baltimore's Inner Harbour.
This air-conditioned holiday home offers 49 square metres of living space with two bedrooms, accommodating up to seven guests, and features a rooftop pool with sea views, private dock access, a well-equipped kitchen, and a fireplace.
Semper Fi Condo - Annapolis, MD
10 11 reviews

Semper Fi Condo

apartment, Annapolis
This Annapolis flat offers a prime location just minutes from downtown, the Royal Naval Academy, and waterfront attractions, with Quiet Waters Park and its dog beach approximately 1.3 kilometres away.
This pet-friendly condo for four guests features air conditioning, a full kitchen with fridge, freezer and microwave, two bathrooms, a private balcony, and access to communal swimming pool and gym facilities, with free parking and secure code-entry building access.
Private Art-filled Guesthouse Near Naval Academy - Annapolis, MD
10 171 reviews

Private Art-filled Guesthouse Near Naval Academy

house, Annapolis
This charming guesthouse is located in West Annapolis, a peaceful residential neighbourhood close to Weems Creek and the Severn River, just a few kilometres from the city centre, the Naval Academy, and the stadium. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The guesthouse is a private and peaceful retreat, perfect for couples or solo travellers. It offers a modern kitchen, updated bathroom, and comfortable bedding, along with a blend of antique curios and Americana for a unique and charming atmosphere.
Waterfront Retreat In Riva· Pool, Pier & Kayaks · Sleeps 9 · 15 Min To Annapolis - Annapolis, MD
10 124 reviews

Waterfront Retreat In Riva· Pool, Pier & Kayaks · Sleeps 9 · 15 Min To Annapolis

apartment, Riva
This waterfront property in Cape St. John, Annapolis, boasts stunning South River views, a private dock, and is situated 11.3km from Annapolis city centre and the US Naval Academy, and 5.6km from Westfield Annapolis Mall.
This spacious 204 square metre house offers four bedrooms, three bathrooms, sleeps eight guests, and includes a private pool (May-September), a game room, and a fully equipped kitchen; nearby attractions include Mike's Crab House, just a short drive away.

Best family friendly Annapolis, MD lodging

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

Beautiful Condo - Water View Near City Dock - Annapolis, MD
9.7 235 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.
Beautfiul 7br Home Minutes From Downtown Annapolis - Annapolis, MD
10 1 review

Beautfiul 7br Home Minutes From Downtown Annapolis

apartment, Arnold
This modern colonial property is situated in Arnold, just a short drive from downtown Annapolis and the Naval Academy, offering easy access to the city's attractions and the Chesapeake Bay. The apartment has received excellent ratings for location, cleanliness, and user experience, making it a popular choice for travellers.
This spacious seven-bedroom home can accommodate up to 14 guests, making it perfect for large families or groups. The apartment features a fully equipped kitchen, a large garden, and parking, ensuring a comfortable and enjoyable stay.
Secluded Cozy Cottage In Historic Downtown - Annapolis, MD
9.6 22 reviews

Secluded Cozy Cottage In Historic Downtown

cottage, Annapolis
This charming cottage is located in Annapolis' Historic District, just a short walk from the City Dock and within easy reach of the State House and other key landmarks. The cottage is situated in a quiet neighbourhood, offering a peaceful retreat from the bustling city centre.
The cottage is a spacious two-bedroom property that can comfortably accommodate up to eight guests. It features a modern kitchen, a private patio with a BBQ, and a comfortable living area with an electric fireplace, a 55" Roku TV, and a full daybed.
Restful And Charming Home In Eastport - Annapolis, MD
No reviews

Restful And Charming Home In Eastport

apartment, Annapolis
This three-bedroom apartment in Eastport, Annapolis, is just a short distance from the historic downtown and the US Naval Academy, making it a great base for exploring the city. The area is quiet and residential, offering a peaceful retreat after a day of sightseeing.
The apartment comfortably accommodates six guests and includes a fully equipped kitchen, a spacious living area, and a private terrace with a fire pit. Guests can enjoy the on-site spa, the garden, and the convenience of a washer and dryer in the basement.

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

Spacious Luxe Usna Home - Pool, Hot Tub, Grill - Annapolis, MD
9.6 28 reviews

Spacious Luxe Usna Home - Pool, Hot Tub, Grill

apartment, Annapolis
This seven-bedroom Annapolis property, situated in the Murray Hill district, is less than 1.6km from the US Naval Academy and the Annapolis Civil Rights Plaque.
This smoke-free holiday home boasts 307 square metres of floor space, offering four bathrooms, a fully equipped kitchen, garden, parking and sleeps up to fourteen guests.
Charming Charles -Walkable Downtown Annapolis Home - Annapolis, MD
10 9 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.
Historic Downtown Annapolis Gem Steps To Usna And Main St With Private Patio And Parking - Annapolis, MD
10 27 reviews

Historic Downtown Annapolis Gem Steps To Usna And Main St With Private Patio And Parking

apartment, Annapolis
This charming, fully-renovated house is located in the Historic District of Annapolis, just 0.4 km from the US Naval Academy, St. John's College, and the state capital building. The property has received excellent guest reviews, so you can be sure of a comfortable and enjoyable stay.
The house has three bedrooms, comfortably sleeping up to eight guests. The property offers a range of amenities, including a fully equipped kitchen, a spacious garden, a balcony with picturesque views, and a private backyard with a fire pit.
New Luxury Townhome Near Downtown Annapolis With Multiple Ensuite Bedrooms And Parking - Annapolis, MD
10 1 review

New Luxury Townhome Near Downtown Annapolis With Multiple Ensuite Bedrooms And Parking

apartment, Annapolis
This brand-new, four-level farmhouse-style townhome is located just 3.2 kilometres from the U.S. Naval Academy and 2 kilometres from the Navy-Marine Corps Memorial Stadium, offering a convenient base for exploring Annapolis.
This spacious 210 square metre residence accommodates up to 12 guests with five bedrooms, four en-suite bathrooms, a gourmet kitchen, and a terrace, while being dog-friendly and offering ample parking.

Best Annapolis, MD accommodations with a kitchen

Waterfront Beach House - Annapolis, MD
10 1 review

Waterfront Beach House

apartment, Highland Beach
This 3-bedroom, 3-bathroom flat in Highland Beach offers excellent user, location, and cleanliness ratings, featuring stunning sea views and prime access to beaches and entertainment within 1 kilometre of local restaurants and nightlife.
This property, suitable for up to 8 guests, includes air conditioning, a kitchen with a fridge and microwave oven, and a garden, providing a comfortable stay for couples, solo adventurers, business travellers, and families with children.
Fleet St Retreat In Downtown - Great Location! - Annapolis, MD
9.7 186 reviews

Fleet St Retreat In Downtown - Great Location!

apartment, Annapolis
This two-bedroom townhouse is situated on Fleet Street in Annapolis city centre, just a short walk from the US Naval Academy, the State House and City Dock.
The 84 square metre property offers a modern, fully equipped kitchen, a small patio and sleeps up to five guests, making it ideal for families or groups of friends visiting the area.
Modern Gem Near Historic Annapolis & Naval Academy - Annapolis, MD
10 1 review

Modern Gem Near Historic Annapolis & Naval Academy

house, Annapolis
This detached house is conveniently located in Annapolis, 6.6 kilometres from Annapolis Harbour and the Naval Academy, and 41.8 kilometres from Power Plant.
This property offers 4 bedrooms and 5 bathrooms, accommodating up to 15 guests with a floor area of 242 square meters, air conditioning, a fully equipped kitchen featuring a fridge, microwave oven, and dishwasher, and a garden and parking.
Naptowns Nauti Flat - Annapolis, MD
9.8 43 reviews

Naptowns Nauti Flat

apartment, Annapolis
This Annapolis city centre flat is situated two blocks (approximately 0.16 km) from the Annapolis waterfront and within easy walking distance of historic landmarks such as the United States Naval Academy.
The one-bedroom apartment sleeps four guests and includes a fully equipped kitchen with fridge, freezer, and microwave, plus air conditioning, parking, and a garden; nearby attractions include boutique shops and restaurants.
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