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Vacation rentals in Annapolis

Vacation rentals in Annapolis

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Annapolis

Guests agree: these stays are highly rated for location, cleanliness, and more.

Step Out to Main Street From a Chic Loft
PLUSEntire loft · 4 guests · 1 bed · 1 bath
Step Out to Main Street From a Chic Loft

This loft apartment features an exquisite industrial-chic aesthetic where exposed brick walls and hardwood floors are accentuated by metallic textures and rustic items. Curl up with a book from the bookshelf or sink into the sofa to watch TV.

What guests are saying:

“Great space right in the heart of Annapolis! Everything you need. Poor communication from the owner however. I inquired on my initial booking about staying anything past their published check out time. I got no response until an hour before checkout”

Charming Row House in Historic District
PLUSEntire house · 6 guests · 3 beds · 1 bath
Charming Row House in Historic District

Sip morning coffee beneath a shady parasol on the wooden rear deck overlooking a garden attached to this charming row house. Inside, polished wooden floorboards lend warmth to the homey interior. The front porch hosts a red rocking chair.

What guests are saying:

“This was a perfect place to stay in Annapolis! It's on a quiet street, but a few minute walk away from restaurants, shops, and bars. We received parking passes to be able to park on the residential streets each night, which was really nice. Everything was sparkling clean, the beds were comfortable, and it is filled with all the amenities you could ever need (and more)! We hope to make it back to Annapolis again soon, and would absolutely stay here again!”

As mentioned in the Washington Post
SUPERHOSTEntire house · 6 guests · 2 beds · 1.5 baths
As mentioned in the Washington Post

Our well appointed house in the heart of Annapolis has everything you need for your stay. The house comfortably fits 6 people and is located only literally steps away from all restaurants and the USNA Main Gate. You won't find a nicer back patio.

What guests are saying:

“We spent a long stay at Brad & Kristen's--traveling for work and away from home in a challenging moment and they made the stay as easy as possible for us. The location truly is fantastic, even during the shutdown we were able to take walks and enjoy the beauty of historic Annapolis. House is well set for long stays, especially with a full kitchen/kitchen tools (and the BBQ out back was an added bonus.) Comfortable, enjoyable, and with helpful hosting. Thank you!”

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Annapolis holiday rentals

  • Kitchen
  • Wi-Fi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Annapolis

Sunny Spot Suite, Spacious & Serene,near Annapolis
SUPERHOSTEntire guest suite
Sunny Spot Suite, Spacious & Serene,near Annapolis
Price:$87 NZD / night
Renovated Annapolis Row House a Minute's Walk to USNA
PLUSEntire house
Renovated Annapolis Row House a Minute's Walk to USNA
Price:$237 NZD / night
Beautiful and Tranquil Carriage House
PLUSEntire house
Beautiful and Tranquil Carriage House
Price:$374 NZD / night
COZY & UNIQUE STUDIO - HEART OF DOWNTOWN ANNAPOLIS
SUPERHOSTEntire apartment
COZY & UNIQUE STUDIO - HEART OF DOWNTOWN ANNAPOLIS
Price:$159 NZD / night
Modern Apartment over the Heart of Main Street!
SUPERHOSTEntire apartment
Modern Apartment over the Heart of Main Street!
Price:$176 NZD / night
Wright’s Cottage- No cleaning fees! Pets! River!
SUPERHOSTEntire house
Wright’s Cottage- No cleaning fees! Pets! River!
Price:$167 NZD / night
Chesapeake Birdhouse Studio
SUPERHOSTEntire guesthouse
Chesapeake Birdhouse Studio
Price:$205 NZD / night
Howard's Cove Retreat
SUPERHOSTPrivate room
Howard's Cove Retreat
Price:$110 NZD / night
New Hotel Chic
SUPERHOSTEntire house
New Hotel Chic
Price:$333 NZD / night
Detached bedroom, private entrance, en-suite bath!
SUPERHOSTPrivate room
Detached bedroom, private entrance, en-suite bath!
Price:$106 NZD / night
Brand New Reno in Historic Dist w 2 Parking spots
SUPERHOSTEntire apartment
Brand New Reno in Historic Dist w 2 Parking spots
Price:$222 NZD / night
Edgewater/Mayo Getaway! **Please, no parties!!**
SUPERHOSTEntire house
Edgewater/Mayo Getaway! **Please, no parties!!**
Price:$595 NZD / night
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