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Holiday 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.

Annapolis Treehouse Apartment- separate space
Entire guest house · 3 guests · 1 bed · 1 bathroom

Annapolis Treehouse Apartment- separate spaceAbout this space This private treehouse apartment, located above a detached garage, is nestled among the treetops on a wooded acre of land in a friendly, walkable, and quiet neighborhood. The apartment is a beautiful space with modern furniture, vinyl plank floors, a king-size bed, and a 50-inch flat-screen TV. We are located 3 miles from historic downtown Annapolis, the Naval Academy, and the Naval Athletic stadium.

Wall to Wall Cool- Filled with Original Art and Sculpture
PLUS
Entire flat · 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.

Old Bay Bungalow
SUPERHOST
Entire guest suite · 4 guests · 2 beds · 1 bathroom

Old Bay BungalowThis in-law apartment located in the lower level of our occupied home is just moments outside of Annapolis, mere blocks from the Magothy River. We enjoy inviting guests into our home, and take pride in treating new friends like family. Come rest your weary bones in your private retreat with its own separate entrance, relaxing sunporch, and stocked kitchenette. Reach into the fridge and enjoy cold soda or a local beer on us! Sit around our fireplace and relax. Settle into the Old Bay Bungalow!

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Popular amenities for Anne Arundel County holiday rentals

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

Other great holiday rentals in Anne Arundel County

SUPERHOST
  1. Entire cottage
  2. Annapolis
Mill Creek Cottage
SUPERHOST
  1. Entire house
  2. Glen Burnie
Secluded acre near BWI and Baltimore
  1. Entire flat
  2. Annapolis
Downtown Gem in Historic Annapolis
SUPERHOST
  1. Entire cottage
  2. Pasadena
Ft. Smallwood Overlook. It's all about the water!
SUPERHOST
  1. Private room
  2. Elkridge
The Rowanberry Condo
SUPERHOST
  1. Private room
  2. Annapolis
Private & Spacious - 3 miles to Downtown Annapolis
  1. Entire guest suite
  2. Annapolis
Annapolis Guest Suite, dogs allowed
  1. Entire guest house
  2. Stevensville
Waterfront Getaway - View of bay from your bed
SUPERHOST
  1. Private room
  2. Annapolis
Howard's Cove Retreat
SUPERHOST
  1. Entire flat
  2. Annapolis
Walk to Water, State House, USNA
PLUS
  1. Entire house
  2. Annapolis
Charming Row House in Historic District
  1. Entire house
  2. Pasadena
Magothyville - Cozy Private Guest Suite (1000 SF)