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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.

  • 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.”

  • 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:

    “From the get go, Steve was quick to respond even prior to our stay. We needed to check in early and he was very accommodating to our arrival needs. The house was so beautiful & clean. We were greeted with a bottle of wine and, thankfully as we arrived before 9am, there was a coffee station in the kitchen too which was very much needed! The details and accommodations he had to make our stay more comfortable were totally noticed (iPhone charger in the kitchen, coffee station, toiletries in the bathroom, etc...) The bed was so comfortable as well! Also, it was a quick 5 minute drive to the downtown area. I would absolutely stay here again the next time I am in Annapolis and would recommend everyone else do the same! Thanks, Steve!”

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

Chesapeake Birdhouse Studio
SUPERHOSTEntire guesthouse
Chesapeake Birdhouse Studio
Price:R 2,268 ZAR / night
As mentioned in the Washington Post
SUPERHOSTEntire house
As mentioned in the Washington Post
Price:R 1,344 ZAR / night
Sunny Spot Suite, Spacious & Serene,near Annapolis
SUPERHOSTEntire guest suite
Sunny Spot Suite, Spacious & Serene,near Annapolis
Price:R 840 ZAR / night
Step Out to Main Street From a Chic Loft
SUPERHOSTEntire loft
Step Out to Main Street From a Chic Loft
Price:R 1,697 ZAR / night
Modern Waterview Condo
Entire condominium
Modern Waterview Condo
Price:R 1,596 ZAR / night
COZY & UNIQUE STUDIO - HEART OF DOWNTOWN ANNAPOLIS
SUPERHOSTEntire apartment
COZY & UNIQUE STUDIO - HEART OF DOWNTOWN ANNAPOLIS
Price:R 1,344 ZAR / night
Spacious apartment, private entrance - water views
SUPERHOSTEntire house
Spacious apartment, private entrance - water views
Price:R 1,596 ZAR / night
Cozy Naptown Perch
SUPERHOSTEntire guest suite
Cozy Naptown Perch
Price:R 2,268 ZAR / night
Wright’s Cottage- No cleaning fees! Pets! River!
SUPERHOSTEntire house
Wright’s Cottage- No cleaning fees! Pets! River!
Price:R 1,848 ZAR / night
The Bennett House
SUPERHOSTEntire apartment
The Bennett House
Price:R 2,184 ZAR / night
Chesapeake Mornings
SUPERHOSTPrivate room
Chesapeake Mornings
Price:R 840 ZAR / night
King George Hideaway - Park & Walk Everywhere
SUPERHOSTEntire apartment
King George Hideaway - Park & Walk Everywhere
Price:R 2,268 ZAR / night
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