Search accommodations in Annapolis, MD

856 available accommodation offers

7 nights
2
1
  • airbnb
  • booking
  • makemytrip
  • oyo
  • yatra
  • goibibo
  • travelguru
  • cleartrip
  • vrbo
  • expedia
  • hotelscom
  • tripcom
  • agoda
Annapolis, MD place to stay
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

856 Lodgings in Annapolis, MD

Best Annapolis, MD lodging with a pool

Among the 856 accommodations in Annapolis, MD, here are the 4 best ones with a pool

Waterfront 2-bedroom Condo On Spa Creek - Annapolis, MD
10 12 reviews
Annapolis, MD
06/11 – 08/11
₹64477/nighttotal: ₹128954 (2 )

Waterfront 2-bedroom Condo On Spa Creek

2 2
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.
Sailboat Experience In Annapolis - Annapolis, MD
8.8 5 reviews
Annapolis, MD
25/06 – 28/06
₹26496/nighttotal: ₹79488 (3 )

Sailboat Experience In Annapolis

1 2
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.
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
Annapolis, MD
01/01 – 01/02
₹36468/nighttotal: ₹1130508 (31 )

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.

1 2
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.
Spa Creek Condo | Pool, Deck & Parking - Annapolis, MD
10 5 reviews
Annapolis, MD
17/09 – 22/09
₹37589/nighttotal: ₹187945 (5 )

Spa Creek Condo | Pool, Deck & Parking

1 1
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.

Best family friendly Annapolis, MD lodging

Among the 856 accommodations in Annapolis, MD, here are the 4 best for families

Cozy 3br Annapolis, Private Deck, Parking - Annapolis, MD
10 14 reviews
Annapolis, MD
25/06 – 28/06
₹49097/nighttotal: ₹147291 (3 )

Cozy 3br Annapolis, Private Deck, Parking

3 2
apartment , Annapolis
This Annapolis apartment is ideally located near the waterfront, within walking distance of shops and restaurants, and a short distance (a few minutes by car) from the United States Naval Academy.
The three-bedroom, two-bathroom flat offers comfortable accommodation for up to six guests, boasting a private deck, fully equipped kitchen, dedicated workspace, and parking – a valuable asset in Annapolis.
Chesapeake Comfort, Annapolis. - Annapolis, MD
9.8 20 reviews
Annapolis, MD
06/11 – 08/11
₹153483/nighttotal: ₹306966 (2 )

Chesapeake Comfort, Annapolis.

3 2
apartment , Annapolis
This Annapolis holiday home is centrally located, less than 0.5 km from Peters Cove and 3.2 km from the United States Naval Academy.
The 186 square metre property boasts three bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, private patio, free Wi-Fi, and access to a spa.
Annapolis Home, Near Downtown - Annapolis, MD
9.6 77 reviews
Annapolis, MD
06/08 – 10/08
₹58015/nighttotal: ₹232060 (4 )

Annapolis Home, Near Downtown

1 10
apartment , Annapolis
This house is located in a quiet residential area, just 6 km from the centre of Annapolis and close to major shopping centres like Whole Foods, Target and the mall. It has excellent ratings for location, cleanliness and user experience.
The house has four bedrooms, two bathrooms and can accommodate up to 11 guests. It offers a fully equipped kitchen, a garden and parking for 4-5 cars.
Historic Row Home In Downtown Annapolis - Annapolis, MD
Annapolis, MD
27/06 – 29/06
₹73469/nighttotal: ₹146938 (2 )

Historic Row Home In Downtown Annapolis

2 2
apartment , Annapolis
This Annapolis apartment, situated in the Historic District, is a short walk (less than 0.8 km) from the US Naval Academy Gate 1, City Dock, and numerous restaurants.
The 102 square metre, two-bedroom dwelling boasts a spacious two-storey layout, sleeps eight guests, and includes a private patio, updated kitchen with dishwasher, and in-unit laundry facilities.

Frequently asked questions about accommodations in Annapolis, MD

  • What are the top attractions and must-see sites in Annapolis, MD?

    You definitely want to visit the United States Naval Academy, a beautiful campus with a rich history. The Maryland State House is another must-see, being the oldest state capitol building in continuous legislative use in the United States. And of course, you can't miss the Annapolis City Dock, a vibrant waterfront area with shops, restaurants, and plenty of boat watching.
  • What are the most convenient modes of transportation within Annapolis, MD?

    Annapolis is a very walkable city, so you can easily get around on foot. There's also a good public bus system, the Annapolis Area Transit (AAT), that can take you to most places. If you're planning to explore further afield, consider renting a car. And don't forget about the water taxis - a fun and scenic way to get around the harbour.
  • What outdoor activities and adventures are popular in and around Annapolis, MD?

    For outdoor enthusiasts, there are plenty of options. You can go kayaking or paddleboarding on the Chesapeake Bay, explore the trails at Quiet Waters Park, or visit the Sandy Point State Park for a day of sun and sand. And if you're feeling adventurous, try sailing on the bay - there are plenty of charter companies offering trips.
  • What types of accommodations are available in Annapolis, MD?

    You'll find a range of accommodation options in Annapolis, from budget-friendly motels and guesthouses to luxurious hotels and waterfront resorts. There are also plenty of vacation rentals available if you're looking for something more spacious or unique.
  • When is the best time to visit Annapolis, MD?

    Spring and autumn are generally the most pleasant times to visit Annapolis, with mild temperatures and less crowds. If you're looking for warm weather and outdoor activities, summer is a good option. And if you enjoy the festive atmosphere, winter offers the charm of the holiday season.
  • What local dishes and culinary experiences are a must-try in Annapolis, MD?

    You have to try some fresh seafood when you're in Annapolis! The Chesapeake Bay is famous for its blue crabs, so make sure to order a crab cake or steamed crabs. And don't forget to try the local oysters, they're delicious! For a sweet treat, head to the famous Carvel ice cream shop, a local favourite.

Destinations nearby

Best Annapolis, MD accommodations with a balcony

Parking At Randall House Across From Usna Gate 1 - Annapolis, MD
9.8 85 reviews
Annapolis, MD
01/01 – 01/02
₹124697/nighttotal: ₹3865607 (31 )

Parking At Randall House Across From Usna Gate 1

4 2
apartment , Annapolis
This house is located in Annapolis' Historic District, within walking distance of the U.S. Naval Academy, City Dock, and John Smith House. The surrounding area is steeped in history, with the Kunta Kinte Plaque & Alex Haley Memorial and 14 Fleet Street just a short walk away. This property has excellent user, location, and cleanliness ratings.
The house offers 4 bedrooms and 4 bathrooms, spanning 322 square metres and accommodating up to 11 guests. Enjoy a fully equipped kitchen, a terrace, a garden, a spa, parking, air conditioning, and free Wi-Fi, making it the perfect base for exploring all that Annapolis has to offer.
New! Private, Family-friendly Home Near Usna - Annapolis, MD
Annapolis, MD
25/06 – 28/06
₹64961/nighttotal: ₹194883 (3 )

New! Private, Family-friendly Home Near Usna

3 2
house , Annapolis
This family-friendly detached house is located in Annapolis, 5.15 kilometres from Annapolis Harbour and 38.62 kilometres from Addison Road-Seat Pleasant.
This accommodation offers 111 square metres of living space with 3 bedrooms, 2 bathrooms, and a capacity for 13 guests, featuring a fully equipped kitchen, air conditioning, a garden, and private parking.
2026 Commissioning Week Promo: Book 6 Nights, Get The 7th Free - Annapolis, MD
10 113 reviews
Annapolis, MD
29/08 – 04/09
₹77240/nighttotal: ₹463440 (6 )

2026 Commissioning Week Promo: Book 6 Nights, Get The 7th Free

2 2
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.
Belle By The Bay Summ - Annapolis, MD
10 4 reviews
Annapolis, MD
17/09 – 22/09
₹46465/nighttotal: ₹232325 (5 )

Belle By The Bay Summ

3 1
apartment , Annapolis
This Annapolis holiday home is situated 0.6km from the Dr Aris T Allen Memorial and 4.7km from the United States Naval Academy, offering easy access to key Annapolis attractions.
Sleeping up to 10 guests, this three-bedroom property boasts a fully equipped kitchen, two bathrooms, a private balcony, garden, parking, and is pet-friendly; nearby amenities include the Wild Bird Center and St John's College.

Best Annapolis, MD accommodations with a kitchen

Cozy Eastport Hideaway | Walk To City Dock & Usna - Annapolis, MD
9.7 18 reviews
Annapolis, MD
06/11 – 08/11
₹34938/nighttotal: ₹69876 (2 )

Cozy Eastport Hideaway | Walk To City Dock & Usna

1 2
apartment , Annapolis
This ground-floor Annapolis flat in Eastport offers convenient street parking and is a short walk from both Eastport's attractions and Annapolis city centre.
The self-contained apartment, sleeping four, features a queen bed, a queen-size sofa bed, a kitchenette, a full bathroom with walk-in shower, smart TV, and free Wi-Fi; nearby activities include exploring the historic sites of Annapolis.
Historic Chapel Views, Steps To Usna Gate 1 With Private Patio And Off-site Parking - Annapolis, MD
9.9 84 reviews
Annapolis, MD
27/06 – 29/06
₹82528/nighttotal: ₹165056 (2 )

Historic Chapel Views, Steps To Usna Gate 1 With Private Patio And Off-site Parking

3 2
apartment , Annapolis
This three-bedroom house is situated in Annapolis' Historic District, within a 1.6 km walk of the US Naval Academy and a 0.8 km walk from the Hammond-Harwood House.
The property offers a spacious 224 square metre living space, perfect for families or groups of up to seven, with a fully equipped kitchen, a patio, and a barbecue grill.
Historic + Modern Home | Just Steps To Waterfront - Annapolis, MD
10 43 reviews
Annapolis, MD
24/07 – 29/07
₹40322/nighttotal: ₹201610 (5 )

Historic + Modern Home | Just Steps To Waterfront

1 3
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.
Historic Naptown Charmer <1mile To Navy-mc Stadium - Annapolis, MD
10 23 reviews
Annapolis, MD
03/12 – 06/12
₹101472/nighttotal: ₹304416 (3 )

Historic Naptown Charmer <1mile To Navy-mc Stadium

6 10
apartment , Annapolis
This six-bedroom Annapolis house is situated in the Downtown area, within walking distance of shops, restaurants, and historical sites, and a short (approx. 0.8 km) drive from the United States Naval Academy.
The spacious property boasts a 4.5-bathroom layout, including a separate two-bedroom guest suite with kitchenette and private deck, comfortably sleeping up to 16 guests and offering amenities such as a garden, parking for five vehicles, and a finished basement.
©2026 cozycozy.com