Skip to content
Sign up
Log in
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:

    “Matt's place was sparkling clean and he came through for us in a really hard time even though he didn't know it. During nationwide quarantine, we had to get to MD Anderson and time was crucial. We decided not to fly due to crowds and one of us being immune compromised. A tough journey under any circumstances, but our whole experience was seemless and we were exposed to less potential hazard by using AirBNB. Of course that also meant we were making a lot of last minute reservations and asking a lot of our hosts. Matt was great!”

  • Renovated Annapolis Row House a Minute's Walk to USNA
    PlusEntire house · 6 guests · 3 beds · 2.5 baths
    Renovated Annapolis Row House a Minute's Walk to USNA

    Make no mistake that this nautically themed house is close to the Naval Academy. Original details have been preserved, such as the charming front porch and interior millwork. A thoughtful renovation has created a luxurious new kitchen and bathrooms.

    What guests are saying:

    “What a gem in the heart of Annapolis! Sits on a quaint street 1 block from the stores & shops. Excellent nautical decor With no clutter. Plenty of space .. & thoughtfully equippied with what we needed for our stay. From the original hard woods floors to an amazing staircase! So much charm. We will definitely be back!”

  • New Hotel Chic
    SUPERHOSTEntire house · 4 guests · 2 beds · 1 bath
    New Hotel Chic

    Just steps from downtown Historic Annapolis, this brand new home is the perfect oasis for any trip. Large yard and gas grill. Light, airy home is quiet and has everything you need. Enjoy a bottle of wine upon your arrival.

    What guests are saying:

    “Steve’s house was just what us weary travelers needed. It was welcoming— equipped with everything a traveler would need (especially the bottle of wine), immaculate, and comfy. Beautiful decor as well. Location is close to downtown, the waterfront and many restaurants. Steve was a very responsive host. Highly recommend.”

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

Wall to Wall Cool- Filled with Original Art and Sculpture
PlusEntire apartment
Wall to Wall Cool- Filled with Original Art and Sculpture
Price:$145 AUD / night
COZY & UNIQUE STUDIO - HEART OF DOWNTOWN ANNAPOLIS
SUPERHOSTEntire apartment
COZY & UNIQUE STUDIO - HEART OF DOWNTOWN ANNAPOLIS
Price:$109 AUD / night
Chesapeake Birdhouse Studio
SUPERHOSTEntire guesthouse
Chesapeake Birdhouse Studio
Price:$196 AUD / night
As mentioned in the Washington Post
Entire house
As mentioned in the Washington Post
Price:$188 AUD / night
Downtown Gem in Historic Annapolis
Entire apartment
Downtown Gem in Historic Annapolis
Price:$217 AUD / night
Pet Friendly Light House
SUPERHOSTPrivate room
Pet Friendly Light House
Price:$66 AUD / night
"Italia Room" Near Downtown Annapolis
SUPERHOSTPrivate room
"Italia Room" Near Downtown Annapolis
Price:$77 AUD / night
Sunny Spot Suite, Spacious & Serene,near Annapolis
SUPERHOSTEntire guest suite
Sunny Spot Suite, Spacious & Serene,near Annapolis
Price:$58 AUD / night
The Bennett House
SUPERHOSTEntire apartment
The Bennett House
Price:$188 AUD / night
Close to Downtown
SUPERHOSTPrivate room
Close to Downtown
Price:$94 AUD / night
Modern Apartment over the Heart of Main Street!
SUPERHOSTEntire apartment
Modern Apartment over the Heart of Main Street!
Price:$144 AUD / night
Rooms at Garden House next to USNA & Harbor
SUPERHOSTPrivate room
Rooms at Garden House next to USNA & Harbor
Price:$145 AUD / night
Show all