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Vacation rentals in Anne Arundel County

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Top-rated holiday rentals in Anne Arundel County

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

Private Eastport guest suite in Annapolis
Entire guest suite · 2 guests · 1 bed · 1 bath
Private Eastport guest suite in AnnapolisEnjoy a convenient, clean, comfortable and private suite in the heart of Eastport. Steps away from Davis’s Pub and Forward Brewing as well as Annapolis’s best restaurants and fun shops and marinas with off street parking. Quick walk to historic Annapolis and the Naval academy. Park your car and enjoy all that Annapolis has to offer on foot! There are two Kayaks and a stand up paddle board for the outdoor enthusiast.
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.
The Riva House
SUPERHOST
Entire guesthouse · 2 guests · 1 bed · 1 bath
The Riva HouseMinutes from downtown Annapolis and Naval Academy and steps away from the famous Mike’s Crabhouse on the South River. 2 miles from route 50 and 30 minutes to both Washington DC and the Baltimore Harbor.

Holiday rentals for every style

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Popular amenities for Anne Arundel County holiday rentals

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

Other great holiday rentals in Anne Arundel County

  1. Entire guest suite
  2. Annapolis
Cozy basement APT 8mins from Downtown Annapolis
$152 AUD per night
SUPERHOST
  1. Entire condominium (condo)
  2. Annapolis
Downtown Annapolis Condo w/ Free Parking + Coffee
$307 AUD per night
  1. Entire residential home
  2. Glenn Dale
Clean and Cozy Private Basement - 15 mins from DC!
$166 AUD per night
  1. Entire residential home
  2. Annapolis
Quiet home with large yard, close to Navy Bridge.
$538 AUD per night
SUPERHOST
  1. Entire residential home
  2. Annapolis
New Hotel Chic
$324 AUD per night
PLUS
  1. Entire residential home
  2. Annapolis
Charming Row House in Historic District
$530 AUD per night
SUPERHOST
  1. Entire guest suite
  2. Arnold
Old Bay Bungalow
$138 AUD per night
  1. Entire residential home
  2. Pasadena
Magothyville - Cozy Private Guest Suite (1000 SF)
$110 AUD per night
SUPERHOST
  1. Entire guesthouse
  2. Annapolis
Chesapeake Birdhouse Studio
$213 AUD per night
SUPERHOST
  1. Entire cabin
  2. Gambrills
Relaxing Cabin Get Away Near Annapolis & DC
$126 AUD per night
  1. Entire cottage
  2. Annapolis
Charming Waterfront Cottage on Historic Property
$982 AUD per night
SUPERHOST
  1. Entire cottage
  2. Annapolis
Mill Creek Cottage
$209 AUD per night