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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 bathroom
    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 !”

  • Chesapeake Mornings
    SUPERHOSTPrivate room · 2 guests · 1 bed · 1.5 bathrooms
    Chesapeake Mornings

    Sun-filled corner room with queen-sized bed, walk-in closet, lovely window shades with pretty views of the front yard. The room is located in a colonial home where people from all backgrounds are very welcome! Perfect location for someone who loves to walk and bike or just relax on the back patio.

    What guests are saying:

    “This was our first “private room” stay. Our hosts made us feel at home, even offering to cook us a hot breakfast. Our arrival was super late due to a very delayed flight, and they were so understanding and and accommodating, they went above and beyond. A beautiful home, and comfortable bed after a long day of traveling were very much appreciated. Thank you!”

  • Wall to Wall Cool- Filled with Original Art and Sculpture
    SUPERHOSTEntire flat · 4 guests · 2 beds · 1 bathroom
    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.”

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

Private Annapolis Inlaw Apartment
SUPERHOSTEntire flat
Private Annapolis Inlaw Apartment
Price:₹6,484 / night
COZY & UNIQUE STUDIO - HEART OF DOWNTOWN ANNAPOLIS
SUPERHOSTEntire flat
COZY & UNIQUE STUDIO - HEART OF DOWNTOWN ANNAPOLIS
Price:₹6,718 / night
New Hotel Chic
SUPERHOSTEntire house
New Hotel Chic
Price:₹14,509 / night
Step Out to Main Street From a Chic Loft
SUPERHOSTEntire loft
Step Out to Main Street From a Chic Loft
Price:₹11,618 / night
Chesapeake Birdhouse Studio
SUPERHOSTEntire guest house
Chesapeake Birdhouse Studio
Price:₹10,045 / night
"Italia Room" Near Downtown Annapolis
SUPERHOSTPrivate room
"Italia Room" Near Downtown Annapolis
Price:₹3,943 / night
As mentioned in the Washington Post
SUPERHOSTEntire house
As mentioned in the Washington Post
Price:₹12,755 / night
The Bennett House
SUPERHOSTEntire flat
The Bennett House
Price:₹9,885 / night
Downtown Gem in Historic Annapolis
Entire flat
Downtown Gem in Historic Annapolis
Price:₹11,246 / night
Wright’s Cottage- No cleaning fees! Pets! River!
SUPERHOSTEntire house
Wright’s Cottage- No cleaning fees! Pets! River!
Price:₹8,185 / night
Adorable Annapolis Apartment!
SUPERHOSTEntire flat
Adorable Annapolis Apartment!
Price:₹10,045 / night
Private Art-Filled Guesthouse near Naval Academy
SUPERHOSTEntire guest house
Private Art-Filled Guesthouse near Naval Academy
Price:₹14,881 / night
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