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Vacation rentals in Annapolis

Vacation rentals in Annapolis

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Annapolis

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

  • Wall to Wall Cool- Filled with Original Art and Sculpture
    PlusEntire 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.”

  • 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!”

  • 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 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 !”

Vacation rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Annapolis vacation rentals

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

Other great vacation rentals in Annapolis

Step Out to Main Street From a Chic Loft
PlusEntire loft
Step Out to Main Street From a Chic Loft
Price:R2,088 ZAR / night
Wall to Wall Cool- Filled with Original Art and Sculpture
PlusEntire apartment
Wall to Wall Cool- Filled with Original Art and Sculpture
Price:R1,754 ZAR / night
COZY & UNIQUE STUDIO - HEART OF DOWNTOWN ANNAPOLIS
SUPERHOSTEntire apartment
COZY & UNIQUE STUDIO - HEART OF DOWNTOWN ANNAPOLIS
Price:R1,316 ZAR / night
Sunny Spot Suite, Spacious & Serene,near Annapolis
SUPERHOSTEntire guest suite
Sunny Spot Suite, Spacious & Serene,near Annapolis
Price:R702 ZAR / night
Charming Row House in Historic District
PlusEntire house
Charming Row House in Historic District
Price:R1,561 ZAR / night
Pet Friendly Light House
SUPERHOSTPrivate room
Pet Friendly Light House
Price:R789 ZAR / night
Chesapeake Birdhouse Studio
SUPERHOSTEntire guesthouse
Chesapeake Birdhouse Studio
Price:R2,368 ZAR / night
1A Annapolis Apartment
Entire apartment
1A Annapolis Apartment
Price:R1,842 ZAR / night
"Italia Room" Near Downtown Annapolis
SUPERHOSTPrivate room
"Italia Room" Near Downtown Annapolis
Price:R930 ZAR / night
As mentioned in the Washington Post
Entire house
As mentioned in the Washington Post
Price:R2,281 ZAR / night
Charming Eastport
SUPERHOSTEntire apartment
Charming Eastport
Price:R1,737 ZAR / night
Modern Apartment over the Heart of Main Street!
SUPERHOSTEntire apartment
Modern Apartment over the Heart of Main Street!
Price:R1,737 ZAR / night
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