Sign up
Log in
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.

  • 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.”

  • Private Annapolis Inlaw Apartment
    SUPERHOSTEntire apartment · 4 guests · 1 bed · 1 bath
    Private Annapolis Inlaw Apartment

    In-law apartment in beautiful Annapolis home. Close to downtown Annapolis but also has easy access to major highways. Quiet neighborhood. Private front entrance to apartment. In addition to king size bed in bedroom there are two queen size blow up beds as well as a large sectional sofa. So it comfortably sleeps 4. Off street parking for 2-3 vehicles.

    What guests are saying:

    “Richard and Pam’s place was beautiful. The accessibility of the in- law suite was excellent, and we had everything we needed from an abundance of towels, toiletries, beddings, it was convenient to have a self- inflatable queen air mattress, which our 3 year old slept comfortably on while the king bed was nice and cozy. Nice amenities, clean, and at a very convenient location in Annapolis. Just know that since it is an in law suite you will hear some noise / footsteps from the main house upstairs. Highly recommend.”

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

As mentioned in the Washington Post
SUPERHOSTEntire house
As mentioned in the Washington Post
Price:$183 / night
Chesapeake Birdhouse Studio
SUPERHOSTEntire guesthouse
Chesapeake Birdhouse Studio
Price:$137 / night
Step Out to Main Street From a Chic Loft
SUPERHOSTEntire loft
Step Out to Main Street From a Chic Loft
Price:$141 / night
The Bennett House
SUPERHOSTEntire apartment
The Bennett House
Price:$131 / night
New Hotel Chic
SUPERHOSTEntire house
New Hotel Chic
Price:$182 / night
Chesapeake Mornings
SUPERHOSTPrivate room
Chesapeake Mornings
Price:$52 / night
Gybeset Eastport Inn
SUPERHOSTEntire apartment
Gybeset Eastport Inn
Price:$115 / night
Private Art-Filled Guesthouse near Naval Academy
SUPERHOSTEntire guesthouse
Private Art-Filled Guesthouse near Naval Academy
Price:$200 / night
Modern Waterfront: Quiet but close to Everything.
SUPERHOSTEntire house
Modern Waterfront: Quiet but close to Everything.
Price:$765 / night
Adorable Annapolis Apartment!
SUPERHOSTEntire apartment
Adorable Annapolis Apartment!
Price:$135 / night
Sophisticated & Spacious Historic Home w/ Parking!
SUPERHOSTEntire house
Sophisticated & Spacious Historic Home w/ Parking!
Price:$458 / night
Downtown Gem in Historic Annapolis
Entire apartment
Downtown Gem in Historic Annapolis
Price:$151 / night
Show all