Owner Direct Vacation
Rentals in Upper Fairmount

There are a lot of options in Upper Fairmount. If you plan on staying in the Upper Fairmount area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Upper Fairmount:

• The Whitehaven Hotel
• Chesapeake Waterfront with Private Dock in Crisfield, Maryland
• Breath-Taking Family Retreat On The Water!
• "Cozy" Waterfront Cottage with Private Pier
• Kingsbay Mansion Bayhouse
• Dog-Friendly Westover Cottage w/River Access!
• Quaint Island Getaway
• Relax on River just south of Salisbury- Recently updated!
• Secluded waterfront getaway with hot tub,fire pit, and private dock.
• Promise Point, Bay Front home with dock 3BR 2BA surrounded by water

There are 2 vacation rentals with private pools near Upper Fairmount. Top-rated homes that have access to a swimming pool include:

• The Best View in the Blue Crab Capital of the World!
• The Cottage at Kingsbay Mansion Executive B&B

If you are looking for a family-friendly vacation home in Upper Fairmount, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Upper Fairmount:

• Crisfield Cabin by Homelystay
• Chesapeake Waterfront with Private Dock in Crisfield, Maryland
• Walk to Local Eats and Docks! Crisfield Getaway

Currently, the total number of properties listed in 2026 is over 102 in the Upper Fairmount area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Upper Fairmount.