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Holiday rentals in Annapolis

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Top-rated holiday rentals in Annapolis

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

Charming Row House in Historic District
PLUS
Entire residential home · 6 guests · 3 beds · 1 bathroom

Charming Row House in Historic DistrictSip 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.

Chesapeake Birdhouse Studio
SUPERHOST
Entire guest house · 2 guests · 1 bed · 1 bathroom

Chesapeake Birdhouse StudioPrivate, clean, cozy studio in the heart of Eastport, Annapolis. Quiet, separate, retreat space. Walk 1 block to restaurants and bars in Eastport, hop on the water taxi and you are in the heart of Downtown Annapolis, USNA, and historic areas of Annapolis in minutes. This is an Ideal location for the sailing community or anyone visiting our beautiful city. Free street parking available. You could park your car and never have to move it through out your stay. Walk, bike or water taxi.

Wall to Wall Cool- Filled with Original Art and Sculpture
PLUS
Entire rental unit · 4 guests · 2 beds · 1 bathroom

Wall to Wall Cool- Filled with Original Art and SculptureBe 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.

Holiday rentals for every style

Get the amount of space that is right for you.

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Popular amenities for Annapolis holiday rentals

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

Other great holiday rentals in Annapolis

SUPERHOST
  1. Entire apartment
  2. Annapolis
Downtown Annapolis Condo w/ Free Parking + Coffee
SUPERHOST
  1. Entire guest house
  2. Annapolis
Calico Cottage Guest House
  1. Entire townhouse
  2. Annapolis
The Perch Annapolis
  1. Entire residential home
  2. Annapolis
Completely updated 4 bedroom in Admiral Heights
SUPERHOST
  1. Entire cottage
  2. Annapolis
Mill Creek Cottage
SUPERHOST
  1. Entire rental unit
  2. Annapolis
Downtown Gem in Historic Annapolis
  1. Entire apartment
  2. Annapolis
The Crow's Nest - Excellent downtown Annapolis Apt
SUPERHOST
  1. Entire residential home
  2. Annapolis
New Hotel Chic
SUPERHOST
  1. Entire rental unit
  2. Annapolis
Private Annapolis Inlaw Apartment
SUPERHOST
  1. Private room
  2. Annapolis
Howard's Cove Retreat
SUPERHOST
  1. Entire apartment
  2. Annapolis
Annapolis Waterfront Condo - Unit #: A-203
SUPERHOST
  1. Entire rental unit
  2. Annapolis
NEW lovely studio apartment with onsite parking!

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