Search accommodations in Annapolis, MD

1103 available accommodation offers

7 nights
2
1
  • airbnb
  • booking
  • hotelscom
  • vrbo
  • tripadvisor
  • expedia
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Annapolis, MD accommodations
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

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 Waterfront | Pool & Parking - Annapolis, MD
10 12 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.
Waterfront Suite With Views Of Annapolis, Prime Eastport Location - Annapolis, MD
10 3 reviews

Waterfront Suite With Views Of Annapolis, Prime Eastport Location

apartment, Annapolis
This Eastport condominium provides waterfront accommodation on Spa Creek, situated 800 meters from downtown Annapolis and a 15-minute walk to the U.S. Naval Academy.
This two-bedroom flat accommodates up to five guests and features a private furnished balcony with sweeping views of Spa Creek and historic Annapolis, alongside access to a seasonal waterfront swimming pool and high-speed Wi-Fi.
Spa Creek Waterfront Pool & Parking - Annapolis, MD
10 1 review

Spa Creek Waterfront Pool & Parking

house, Annapolis
This Annapolis apartment offers direct waterfront access on Spa Creek, placing it a 13-minute walk from Annapolis Harbour and 42 kilometres from Baltimore's Inner Harbour.
This two-bedroom, one-bathroom apartment, accommodating up to seven guests, features a fully equipped kitchen, air conditioning, a swimming pool, fitness centre, and private parking, with a floor area of 60 square metres.
Spacious Luxe Usna Home - Pool, Hot Tub, Grill - Annapolis, MD
9.8 89 reviews

Spacious Luxe Usna Home - Pool, Hot Tub, Grill

apartment, 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.

Best family friendly Annapolis, MD lodging

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

Adorable Home Steps From Navy Stadium! - Annapolis, MD
No reviews

Adorable Home Steps From Navy Stadium!

apartment, Annapolis
This four-bedroom flat in West Annapolis offers immediate access to Annapolis events, situated a mere block from Navy Stadium and within 1.6 kilometres of downtown Annapolis's shops and eateries.
This spacious accommodation for up to eleven guests boasts a deck with a grill, a brick patio with a fire pit, a downstairs wet bar, and two off-street parking spaces, making it ideal for groups attending boat shows or reunions.
Upscale Family Retreat Near Downtown Annapolis | Resort-style Outdoor Spaces - Annapolis, MD
10 3 reviews

Upscale Family Retreat Near Downtown Annapolis | Resort-style Outdoor Spaces

apartment, Annapolis
This four-bedroom, three-bathroom apartment in Annapolis offers convenient access to numerous attractions, being just a 4.8-kilometre drive from the Thurgood Marshall Memorial and 2.4 kilometres from the Navy-Marine Corps Memorial Stadium.
This family-friendly property accommodates up to nine guests, featuring a fully equipped kitchen, air conditioning, free Wi-Fi, a private garden, and is situated near sailing and ice skating opportunities.
Stadium-side Annapolis | Chef Kitchen | Sleeps 10 - Annapolis, MD
9.8 11 reviews

Stadium-side Annapolis | Chef Kitchen | Sleeps 10

apartment, Annapolis
This spacious Annapolis townhouse, ideally situated near the U.S. Naval Academy (two miles away) and Navy-Marine Corps Memorial Stadium, offers easy access to Heineman Park and Harts Cove.
The 223 square metre property boasts four bedrooms, four bathrooms, and sleeps up to ten guests, featuring a chef's kitchen with GE Café appliances, a finished basement, and access to a community pool; kayaking and paddle boarding are readily available at Harts Cove.
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis - Annapolis, MD
9.8 43 reviews

Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis

apartment, Arnold
This spacious seven-bedroom house is located in Cape Saint Claire, a neighbourhood in Annapolis, just 10 kilometres from downtown Annapolis and the United States Naval Academy. It's also close to Kent Island, Baltimore, and Washington D.C., making it a great base for exploring the region. Guests have consistently rated this property as excellent.
The 279 square metre home has a large family room, a bunk room, and 5 bathrooms, comfortably accommodating up to 16 guests. Amenities include a fully equipped kitchen, a private garden, a jacuzzi, a spa, and parking for four 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 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

Pet Friendly Park Free & Walk To Usna Stadium - Annapolis, MD
No reviews

Pet Friendly Park Free & Walk To Usna Stadium

house, Annapolis
This pet-friendly holiday home offers free private parking and is situated just over 3.2 kilometres from Annapolis Harbour and within easy reach of the USNA Stadium.
This spacious 223 square metre property accommodates up to 16 guests across four bedrooms, featuring a well-equipped kitchen, a fitness room, a terrace with city views, and a garden.
Walk To The Naval Academy And Historic Annapolis.  Private Parking At The Home. - Annapolis, MD
10 49 reviews

Walk To The Naval Academy And Historic Annapolis. Private Parking At The Home.

apartment, Annapolis
This three-bedroom, three-bathroom Annapolis holiday home is situated in the Historic District, a mere 0.64 kilometres from the United States Naval Academy and one block from Main Street, five houses from Ego Alley.
Offering off-street parking, a full kitchen, a terrace, and a garden, this property sleeps six guests and is licensed as a vacation rental (STR24-145209), providing easy access to restaurants, pubs, and the Annapolis sailing school.
Brilliantly Updated Multi-level Walkable To Navy Stadium & Close To Historic Downtown Annapolis - Annapolis, MD
10 3 reviews

Brilliantly Updated Multi-level Walkable To Navy Stadium & Close To Historic Downtown Annapolis

apartment, Annapolis
This spacious six-bedroom house is located in Annapolis's Admiral Heights district, offering convenient access to Navy-Marine Corps Memorial Stadium (800 metres) and the U.S. Naval Academy and Historic Downtown Annapolis (both 3.2 kilometres) making it ideal for visitors.
This dog-friendly property boasts 290 square metres of living space, accommodating up to 13 guests with multiple living areas, extensive outdoor entertaining spaces including a screened porch with a television, and driveway parking for four vehicles.
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.

Best Annapolis, MD accommodation with a kitchen

Cute Cozy Rancher Close To Down Town Annapolis - Annapolis, MD
9.6 56 reviews

Cute Cozy Rancher Close To Down Town Annapolis

apartment, Annapolis
This Annapolis rancher, registered as 000489, offers a two-bedroom, one-bathroom property sleeping four, ideally located within Annapolis city limits, with proximity to Annapolis's historical sites and restaurants, although precise distances are not provided.
The eco-friendly property features geothermal heating and solar panels, a fully equipped kitchen including a fridge, microwave, and dishwasher, air conditioning, a garden, and excellent guest ratings across location, cleanliness and overall experience.
18th Cent. Charm In Historic Downtown Annapolis - Annapolis, MD
9.0 14 reviews

18th Cent. Charm In Historic Downtown Annapolis

apartment, Annapolis
This furnished flat is situated in Annapolis's historic district, offering a colonial living experience circa 1770, within a 5-minute walk of Annapolis City Dock and near public parking garages.
This 74 square meter residence accommodates two guests with one bedroom and one bathroom, featuring a kitchenette with a microwave, fridge, and toaster, air conditioning, Wi-Fi, a garden, and parking, all within walking distance of key landmarks like the Kunta Kinte Plaque & Alex Haley Memorial.
Dean Street's Lower Deck House! - Annapolis, MD
9.9 15 reviews

Dean Street's Lower Deck House!

apartment, Annapolis
This Annapolis apartment, located in the Historic District, is within walking distance of shops, restaurants, and the United States Naval Academy.
The one-bedroom, one-bathroom flat offers a queen-size bed, a sleeper sofa, a private patio, backyard access, and a kitchen equipped with a fridge, microwave, and dishwasher, accommodating up to three guests.
Historic Downtown Annapolis W/ Rooftop Deck - Annapolis, MD
9.9 28 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.
©2026 cozycozy.com