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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

Prime Eastport Location - Waterfront Condo W Pool & Parking - Annapolis, MD
10 32 reviews

Prime Eastport Location - Waterfront Condo W Pool & Parking

apartment, Annapolis
This Annapolis apartment, situated in Eastport, is less than 2km from Spa Creek and the United States Naval Academy, offering easy access to the Kunta Kinte-Alex Haley Memorial and Maynard-Burgess House within a 15-minute drive.
The three-bedroom, two-bathroom property sleeps seven guests and includes a full kitchen, terrace, free Wi-Fi, on-site parking, and swimming pool access; nearby attractions include the Naval Academy and the Chesapeake Bay.
Sailboat Experience In Annapolis - Annapolis, MD
8.8 5 reviews

Sailboat Experience In Annapolis

boat, Annapolis
This Annapolis sailboat, a 10-minute walk from Annapolis Harbour, is situated 49.9 kilometres from Carroll Park and 35.4 kilometres from Baltimore-Washington International Thurgood Marshall Airport.
This 150-square-metre vessel offers one bedroom, one bathroom, sleeps four guests, and boasts a fully equipped kitchen, air conditioning, Wi-Fi, and a seasonal outdoor pool; enjoy nearby sailing and explore Annapolis's historic waterfront.
Lakefront Home With Private Pool, Hot Tub, Outdoor Space, Central Ac, & W/d - Annapolis, MD
10 1 review

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.
Semper Fi Condo - Annapolis, MD
9.9 32 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.

Best family friendly Annapolis, MD lodging

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

4br Family Retreat Near Annapolis W/ Large Yard - Annapolis, MD
No reviews

4br Family Retreat Near Annapolis W/ Large Yard

house, Annapolis
This Anchorage waterfront community residence offers a convenient base, located just 1.9 kilometres from downtown Annapolis.
This four-bedroom, two-bathroom detached house accommodates up to eight guests and features a modern kitchen, air conditioning, a garden with a fire pit and grill, and off-street parking, ideal for family holidays and group stays near the Chesapeake Bay.
Historic Eastport Firehouse W Parking, Dogs Ok - Annapolis, MD
10 116 reviews

Historic Eastport Firehouse W Parking, Dogs Ok

apartment, Annapolis
This holiday home is located in Eastport, Annapolis, within a 1.6km walk of the Annapolis Maritime Museum, U.S. Naval Academy, and Spa Creek, making it ideal for exploring the city's attractions. The property has received excellent ratings for location, cleanliness, and overall user experience.
The 223 square metre home can accommodate up to 8 guests in its three bedrooms and has a sofa bed. Guests can enjoy a range of amenities, including a garden, a spa, a terrace, and a barbecue.
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.
Annapolis Charm 3br Downtown - Annapolis, MD
10 1 review

Annapolis Charm 3br Downtown

house, Annapolis
This family-friendly 3-bedroom detached house is situated in Downtown Annapolis, 3.5 kilometres from Annapolis Harbour and 32 kilometres from the Baltimore-Washington International Airport.
This non-smoking accommodation offers free on-site parking, complimentary WiFi, air conditioning, and a garden, with a guest capacity of 13.

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 Charmer <1mile To Nmc Stadium - Annapolis, MD
9.8 7 reviews

Historic Annapolis Charmer <1mile To Nmc Stadium

apartment, Annapolis
This Annapolis apartment, situated a short walk from the city centre and a short drive (approximately 1-2km) from the United States Naval Academy and Navy-Marine Corps Stadium, offers convenient access to Annapolis's key attractions.
This spacious 465 square metre dwelling boasts five bedrooms, five bathrooms, and sleeps up to 21 guests, featuring multiple living areas, a well-equipped kitchen, a garden, tennis court, parking, and proximity to Ego Alley, Great Frogs Winery, and Helen Avalynne Tawes Garden.
Stylish + Fresh Bungalow 2 Blocks From N-mc Stadium - Annapolis, MD
No reviews

Stylish + Fresh Bungalow 2 Blocks From N-mc Stadium

house, Annapolis
House to rent. This accommodation is based in Annapolis.
Services and facilities: a kitchen, a barbecue and a terrace. Take advantage of the Free Parking with this accommodation in Annapolis!
First Mate - Annapolis, MD
No reviews

First Mate

house, Annapolis
This Eastport residence provides direct views of the Severn River and is located less than 1 kilometre from Downtown Annapolis and the United States Naval Academy.
This spacious detached house accommodates up to 12 guests with 4 bedrooms and 4 bathrooms, featuring a gourmet kitchen, a private garden with a fire pit and gas grill, high-speed WiFi, and convenient parking for 2-4 cars.
Hidden Wine Cellar Eastport Retreat - Annapolis, MD
No reviews

Hidden Wine Cellar Eastport Retreat

house, Annapolis
Hidden Wine Cellar Eastport Retreat is a detached house situated in Annapolis's Eastport district, 2.25 kilometres from Annapolis Harbour and 41.84 kilometres from Addison Road-Seat Pleasant.
This 186 square metre dwelling accommodates up to 10 guests across 2 bedrooms, featuring air conditioning, a fully equipped kitchen, a private balcony, and complimentary private parking, with garden access and cycling opportunities nearby.

Best Annapolis, MD accommodation with a kitchen

"Around The Corner" From Eastport Hot Spots With Fenced-in Yard And Parking - Annapolis, MD
10 34 reviews

"Around The Corner" From Eastport Hot Spots With Fenced-in Yard And Parking

apartment, Annapolis
This Annapolis holiday home is centrally located, within 2km of Spa Creek and the United States Naval Academy, offering easy access to the Annapolis Maritime Museum and the Maynard-Burgess House.
The 139 square metre property sleeps eight guests in three bedrooms, two bathrooms, and features a fully equipped kitchen, terrace, garden, spa, parking, and Wi-Fi.
Spacious Home With An Outdoor Pool, Screened Porch, Washer/dryer & Central Ac - Annapolis, MD
No reviews

Spacious Home With An Outdoor Pool, Screened Porch, Washer/dryer & Central Ac

apartment, Highland Beach
This Highland Beach flat is located in a family-friendly neighbourhood between Fishing Creek and the South River, a mere 3.2 kilometres from downtown Annapolis and within walking distance of Thomas Point Park.
This 279 square metre holiday home offers 4 bedrooms, 3 bathrooms, and can accommodate up to 10 guests, featuring a heated saltwater swimming pool, a screened porch, a large updated kitchen, and a fireplace.
Unique Eastport Bungalow W/ Yard - Annapolis, MD
No reviews

Unique Eastport Bungalow W/ Yard

house, Annapolis
This restored four-bedroom, three-bathroom house is situated in Annapolis' historic Eastport district, offering immediate access to local attractions and a highly walkable environment.
This dog-friendly property accommodates up to eight guests with modern amenities including air conditioning and Wi-Fi, complemented by a fenced garden, front porch, and back patio, all within a neighbourhood known for its friendly atmosphere.
Pet Friendly Retreat Near Downtown Annapolis - Annapolis, MD
No reviews

Pet Friendly Retreat Near Downtown Annapolis

house, Annapolis
This family-friendly dwelling is located in a peaceful district of Annapolis, offering convenient access to the historic district, waterfront, and the United States Naval Academy.
This property accommodates up to four guests across two bedrooms and one bathroom, featuring a fully equipped kitchen with a fridge, freezer, and dishwasher, air conditioning, a garden, and parking.
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