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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 bathroom
    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 bathrooms
    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!”

  • "Italia Room" Near Downtown Annapolis
    SUPERHOSTPrivate room · 2 guests · 1 bed · 1 shared bathroom
    "Italia Room" Near Downtown Annapolis

    One block from the USN stadium and a 20 minute walk to downtown Annapolis. A double bed, shared bath, off-street parking and a landscaped backyard with a brick patio. Bathroom may be shared with other B & B guests and there is no TV in the house.

    What guests are saying:

    “Jane's home is pleasant, clean, and free of complications. Jane has done plenty of traveling and understands what travelers need and want. Social interaction levels are what you want them to be. Food is high quality and the place could not possibly be cleaner. Communication before and during the stay was quickly answered and easy to arrange. The neighborhood is the nicest in town, with nearby mass transit and plenty of places within walking distance. We stayed with Jane once before and plan to do so again!”

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
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Annapolis

Step Out to Main Street From a Chic Loft
PlusEntire loft
Step Out to Main Street From a Chic Loft
Price:₹8,928 / night
COZY & UNIQUE STUDIO - HEART OF DOWNTOWN ANNAPOLIS
SUPERHOSTEntire flat
COZY & UNIQUE STUDIO - HEART OF DOWNTOWN ANNAPOLIS
Price:₹5,627 / night
Renovated Annapolis Row House a Minute's Walk to USNA
PlusEntire house
Renovated Annapolis Row House a Minute's Walk to USNA
Price:₹5,927 / night
Wall to Wall Cool- Filled with Original Art and Sculpture
PlusEntire flat
Wall to Wall Cool- Filled with Original Art and Sculpture
Price:₹7,503 / night
Sunny Spot Suite, Spacious & Serene,near Annapolis
SUPERHOSTEntire guest suite
Sunny Spot Suite, Spacious & Serene,near Annapolis
Price:₹3,001 / night
Pet Friendly Light House
SUPERHOSTPrivate room
Pet Friendly Light House
Price:₹3,376 / night
Chesapeake Birdhouse Studio
SUPERHOSTEntire guest house
Chesapeake Birdhouse Studio
Price:₹10,129 / night
As mentioned in the Washington Post
Entire house
As mentioned in the Washington Post
Price:₹9,754 / night
1A Annapolis Apartment
Entire flat
1A Annapolis Apartment
Price:₹8,628 / night
Basement apartment in Heart of Eastport! : )
SUPERHOSTPrivate room
Basement apartment in Heart of Eastport! : )
Price:₹6,377 / night
Modern Apartment over the Heart of Main Street!
SUPERHOSTEntire flat
Modern Apartment over the Heart of Main Street!
Price:₹7,428 / night
"Italia Room" Near Downtown Annapolis
SUPERHOSTPrivate room
"Italia Room" Near Downtown Annapolis
Price:₹3,976 / night
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