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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.

  • Charming Row House in Historic District
    SUPERHOSTEntire 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 place is a gem. Sean and Ami are amazing hosts- who, if I had to guess- have extensive experience working in the hospitality sector. The location is wonderful. It's a quaint street, classic Annapolis row-house, with multiple parks within a <2 minute walk. You are staying in the heart of downtown Annapolis. Whether you're looking for great food, going to a Navy game, exploring the historic homes and gardens, this town has something for everyone. The house is perfectly curated with amazing detail / decor. Sunlight pours through the front of the home and windows on both sides allow for great airflow. Appliances are new, infrastructure and utilities are 10/10- it feels like a five-star hotel manages a quaint home. I can't remember the last time I wrote a review on AirBnB- and can't remember the last time I had such a perfect / charming experience on AirBnB. Excited to come back !”

  • Wall to Wall Cool- Filled with Original Art and Sculpture
    SUPERHOSTEntire apartment · 4 guests · 2 beds · 1 bath
    Wall to Wall Cool- Filled with Original Art and Sculpture

    Be inspired by rooms that flow together like a private exhibition space for the creations of Tommy Urbans. The house is open and airy, a great way to get your zen on. Spend a cozy evening in front of a gas fire and have nightcaps on the front porch.

    What guests are saying:

    “Tom's place offered everything we needed in an Airbnb and more! Parking is just a few steps from the key-coded entry, the bed is comfortable, the shower is spacious and the decor far exceeds anywhere we have ever stayed. The artistic flair added a very pleasurable feel to our stay.”

  • 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

Chesapeake Birdhouse Studio
SUPERHOSTEntire guesthouse
Chesapeake Birdhouse Studio
Price:$206 NZD / night
Private Annapolis Inlaw Apartment
SUPERHOSTEntire apartment
Private Annapolis Inlaw Apartment
Price:$114 NZD / night
New Hotel Chic
SUPERHOSTEntire house
New Hotel Chic
Price:$334 NZD / night
The Bennett House
SUPERHOSTEntire apartment
The Bennett House
Price:$200 NZD / night
Step Out to Main Street From a Chic Loft
SUPERHOSTEntire loft
Step Out to Main Street From a Chic Loft
Price:$238 NZD / night
Chesapeake Mornings
SUPERHOSTPrivate room
Chesapeake Mornings
Price:$79 NZD / night
Private Art-Filled Guesthouse near Naval Academy
SUPERHOSTEntire guesthouse
Private Art-Filled Guesthouse near Naval Academy
Price:$305 NZD / night
Charming home close to downtown.
SUPERHOSTEntire apartment
Charming home close to downtown.
Price:$292 NZD / night
Modern Waterfront: Quiet but close to Everything.
SUPERHOSTEntire house
Modern Waterfront: Quiet but close to Everything.
Price:$1,426 NZD / night
Adorable Annapolis Apartment!
SUPERHOSTEntire apartment
Adorable Annapolis Apartment!
Price:$206 NZD / night
Gybeset Eastport Inn
SUPERHOSTEntire apartment
Gybeset Eastport Inn
Price:$197 NZD / night
Downtown Gem in Historic Annapolis
Entire apartment
Downtown Gem in Historic Annapolis
Price:$231 NZD / night
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