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Annapolis, MD accommodations
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1103 Lodgings in Annapolis, MD

Best Annapolis, MD lodging with a pool

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

Spa Creek Condo | Pool, Deck & Parking - Annapolis, MD
10 15 reviews

Spa Creek Condo | Pool, Deck & Parking

apartment, Annapolis
This Eastport condo provides waterfront living on Spa Creek, a mere 500-metre walk from Downtown Annapolis and the US Naval Academy.
This one-bedroom flat, accommodating up to four guests, features a fully equipped kitchen, air conditioning, a swimming pool, garden, and parking for two vehicles, with a covered deck offering direct Spa Creek views and seasonal access to a shared dock.
Rooftop Pool And Spa Creek Views - Luxurious Waterfront Retreat - Annapolis, MD
No reviews

Rooftop Pool And Spa Creek Views - Luxurious Waterfront Retreat

apartment, Annapolis
This waterfront condo in a quiet Eastport cul-de-sac offers Spa Creek views and is located 800 metres from downtown Annapolis and 1.3 kilometres from the U.S. Naval Academy.
This family-friendly apartment features two bedrooms and two bathrooms, accommodating up to seven guests, with amenities including air conditioning, a swimming pool, a furnished balcony, and off-street parking for two cars.
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
10 1 review

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.
The Pool Loft At Poplar Hill - Annapolis, MD
9.7 4 reviews

The Pool Loft At Poplar Hill

apartment, Arnold
The Pool Loft at Poplar Hill, a one-bedroom apartment in Annapolis, Maryland, is situated 14.8 km from Annapolis Harbour and 41.8 km from Baltimore's Inner Harbour and Camden Yards.
This 65 square metre flat sleeps seven guests and offers amenities including a fully equipped kitchen with dishwasher, a swimming pool, garden, parking, and free Wi-Fi.

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 77 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.
Steps To Usna With Large Private Patio & Free Off-site Parking - Annapolis, MD
9.8 10 reviews

Steps To Usna With Large Private Patio & Free Off-site Parking

apartment, Annapolis
This Annapolis apartment rental is centrally located, within 0.8 to 1.6 kilometres of the United States Naval Academy and less than 1.6 kilometres from the Navy-Marine Corps Memorial Stadium.
Sleeping six guests across three bedrooms and two bathrooms, this renovated property boasts a gourmet kitchen with stainless-steel appliances, a private backyard with patio furniture, and amenities including a washer/dryer and a Blackstone griddle.
4 Bedrooms, 7 Beds, 3 Bath Completely Updated - Annapolis, MD
9.9 137 reviews

4 Bedrooms, 7 Beds, 3 Bath Completely Updated

apartment, Annapolis
This Annapolis holiday home, near the headwaters of Weems Creek, offers easy access to Annapolis's historic district and waterfront attractions, within a short driving distance (exact distances unspecified).
The spacious property boasts a ground-floor layout sleeping eight guests across four bedrooms and three bathrooms, featuring a fully equipped kitchen, multiple living areas, a private deck overlooking Weems Creek, a PS5, and ample outdoor games.
Quintessential Annapolis Charm - Annapolis, MD
No reviews

Quintessential Annapolis Charm

apartment, Annapolis
This three-bedroom, two-bathroom flat offers accommodation for six guests in downtown Annapolis, a short walk from the waterfront, shops, and restaurants.
This historic duplex features a kitchen with a fridge, microwave oven, and dishwasher, air conditioning, and a garden, making it a family-friendly option for exploring Annapolis.

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 and charm! You absolutely have to visit the United States Naval Academy, the Maryland State House, and the historic Annapolis City Dock. Don't miss the chance to explore the beautiful gardens at the William Paca House and Garden.
  • 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 Springhill Suites By Marriott Annapolis are the most popular ones.

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

    The Annapolis Summerfest is a big one, with live music and arts and crafts. You'll also want to check out the Annapolis Maritime Museum's annual Seafood Festival, and the Annapolis Wine Festival in the spring. And, of course, there's the annual Annapolis Boat Show, which is a must-see for any sailing enthusiast.
  • What are the best accommodations with a pool in Annapolis, MD?

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

    Annapolis is a very walkable city, especially in the downtown area. You can easily get around on foot or by bike. If you're coming from further afield, the Annapolis Area Transit buses are a good option, and you can also get around by taxi or ride-sharing services.
  • 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 right on the Chesapeake Bay, so you can enjoy a variety of water activities, like sailing, kayaking, and fishing. If you're looking for something a little more adventurous, you can go hiking or biking on the scenic trails at Quiet Waters Park or the Anne Arundel County Natural Resources Park.
  • What are the best accommodations for families and kids in Annapolis, MD?

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

    You've got a good range of options in Annapolis. There are plenty of hotels, from budget-friendly to luxury, as well as bed and breakfasts, guesthouses, and even some vacation rentals. You can find something to suit any taste and budget.
  • What are the best pet friendly accommodations in Annapolis, MD?

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

    Spring and autumn are ideal, with pleasant weather and fewer crowds. Summer is beautiful, but it can get hot and humid, and the city is very busy. If you want to see the city decked out for the holidays, then winter is a good time to visit, but be prepared for chilly temperatures.
  • What 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, of course! Crab cakes are a local favourite, and you can find them at many restaurants in the city. Also, don't miss the chance to enjoy a delicious meal at one of the many waterfront restaurants, with stunning views of the Chesapeake Bay.
  • In which part of Annapolis, MD should you consider renting accommodation?

    If you want to be in the heart of the action, then downtown Annapolis is the place to be. If you prefer a quieter stay, then you might want to consider staying in the historic district, or even in one of the nearby suburbs, like Eastport or West Annapolis.

Popular destinations

Best Annapolis, MD accommodation with a balcony

Historic Annapolis Home | 2 Blocks To Main St - Annapolis, MD
10 21 reviews

Historic Annapolis Home | 2 Blocks To Main St

apartment, Annapolis
This Annapolis holiday home is situated in the Historic District, within a 0.9km walk of the US Naval Academy and Maynard-Burgess House, and under 0.5km from the Maryland Federation of Art and Ellen O Moyer Nature Park.
The 1174 square metre property boasts four bedrooms, two bathrooms, sleeps nine guests, and includes a fully equipped kitchen, private garden, terrace, free Wi-Fi, and barbecue facilities.
Gorgeous 6-bedroom Charming Annapolis Retreat - Annapolis, MD
No reviews

Gorgeous 6-bedroom Charming Annapolis Retreat

apartment, Annapolis
This six-bedroom, five-bathroom flat is situated in the Hillsmere district of Annapolis, offering convenient access to Great Frogs Winery, just a short walk away, and Maryland Quiet Waters Park, a mere 1-minute drive.
This property accommodates up to 12 guests and includes amenities such as Wi-Fi, a dishwasher, microwave, oven, barbecue, fireplace, and in-unit laundry facilities.
Beachfront Home Minutes To Downtown Annapolis Dogs Ok - Annapolis, MD
9.8 44 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.
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 accommodation with a kitchen

Historic Downtown Annapolis W/ Rooftop Deck - Annapolis, MD
9.9 29 reviews

Historic Downtown Annapolis W/ Rooftop Deck

apartment, Annapolis
This Annapolis townhome, situated on Fleet Street in the city centre, is a half block from Main Street Circle and Annapolis City Dock, offering easy access to shops, restaurants, and the US Naval Academy.
The two-bedroom property, sleeping up to six guests, features a fully equipped kitchen, two outdoor patios (one rooftop), a comfortable living room with a smart TV, and modern amenities including air conditioning and a dishwasher.
Historic Annapolis Retreat  Steps From The Statehouse & City Dock With Parking And Private Patio - Annapolis, MD
10 7 reviews

Historic Annapolis Retreat Steps From The Statehouse & City Dock With Parking And Private Patio

apartment, Annapolis
This historic five-bedroom flat in Annapolis, a property over 175 years old, is located just 160 metres from City Dock and 320 metres from the United States Naval Academy, placing it within easy walking distance of numerous shops, restaurants, and the Maryland Statehouse.
This dog-friendly residence comfortably accommodates up to eight guests, offering modern amenities including air conditioning, Wi-Fi, a fully equipped kitchen with a double oven, and a private fenced patio with a gas grill, all within a setting that showcases exposed brick and original beams.
Charming Garden Row Home, Easy 4 Block Walk To The Heart Of Annapolis. - Annapolis, MD
10 142 reviews

Charming Garden Row Home, Easy 4 Block Walk To The Heart Of Annapolis.

apartment, Annapolis
This property is located in Annapolis' Historic District, just a short walk (less than 1 kilometre) from Chase Lloyd House and the U.S. Naval Academy. It has received excellent user ratings, making it a popular choice for travellers.
This charming house has three bedrooms and two bathrooms, comfortably accommodating up to six guests. The kitchen is fully equipped with a fridge, microwave, dishwasher, and a private garden, allowing guests to enjoy meals at home and relax outdoors.
Port Of Call: 5br Modern Nautical Luxury - Annapolis, MD
10 4 reviews

Port Of Call: 5br Modern Nautical Luxury

apartment, Annapolis
This Annapolis flat is located in the private Anchorage community, 100 metres from the community marina and Lake Ogleton, and a 10-15 minute drive from historic Annapolis and the United States Naval Academy.
This five-bedroom, three-bathroom residence accommodates up to eight guests, featuring a chef's kitchen with a gas range, dual living areas, a large private fenced garden with a firepit, and air conditioning, with internet and parking provided.
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