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Vacation 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.

Chesapeake Birdhouse Studio
SUPERHOST
Entire guesthouse · 2 guests · 1 bed · 1 bath

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 bath

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.

Cozy basement APT 8mins from Downtown Annapolis
Entire guest suite · 3 guests · 1 bed · 1 bath

Cozy basement APT 8mins from Downtown AnnapolisBeautiful guest apartment in an amazing and historic city!!! Guests enjoy our close proximity to downtown Annapolis (5 miles). We offer a studio apartment with one bed, one full bath, living area, and partial kitchen. We are located exactly in the middle of Washington D.C. and Baltimore and are right off of route 50. We have tons of recommendations for your stay.

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Popular amenities for Annapolis holiday rentals

  • Kitchen
  • Wi-Fi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Annapolis

SUPERHOST
  1. Entire condominium (condo)
  2. Annapolis
Downtown Annapolis Condo w/ Free Parking + Coffee
$315 AUD per night
SUPERHOST
  1. Entire rental unit
  2. Annapolis
Private Annapolis Inlaw Apartment
$118 AUD per night
  1. Private room
  2. Annapolis
Annapolis 1 bedroom quest suite
$70 AUD per night
PLUS
  1. Entire guesthouse
  2. Annapolis
Private Art-Filled Guesthouse near Naval Academy
$280 AUD per night
SUPERHOST
  1. Entire cottage
  2. Annapolis
Mill Creek Cottage
$214 AUD per night
  1. Entire rental unit
  2. Annapolis
USNA Chapel- Gate 3 Top floor Pied a Terre Apt
$331 AUD per night
PLUS
  1. Entire residential home
  2. Annapolis
Charming Row House in Historic District
$439 AUD per night
  1. Entire residential home
  2. Annapolis
Quiet home with large yard, close to Navy Bridge.
$582 AUD per night
  1. Entire condominium (condo)
  2. Annapolis
The Crow's Nest - Excellent downtown Annapolis Apt
$224 AUD per night
SUPERHOST
  1. Entire condominium (condo)
  2. Annapolis
Annapolis Waterfront Condo - Unit #: A-203
$212 AUD per night
SUPERHOST
  1. Entire residential home
  2. Annapolis
As mentioned in the Washington Post
$228 AUD per night
SUPERHOST
  1. Entire residential home
  2. Annapolis
New Hotel Chic
$332 AUD per night

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