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An Ideal Way to Enjoy a Stay on Scenic Shelter Island

Shelter Island’s renowned location 100 miles outside of New York City has it all -- tennis in the Heights and Moussa Drame Tennis Academy at the Pridwin; Hampshire Farms Stables; Heights Beach Club; Golf at Gardiners Bay Country Club or Shelter Island Golf Club; Junior Sailing at the Shelter Island yacht Club; Shelter Island Yoga & Fitness at the Dering Harbor Inn; Shelter Island Fit Center & Yoga and Barr classes in the Center

Charming Year Round & Seasonal Getaways

We offer Shelter Island rentals to suit all occasions, including:

  • Seasonal, Monthly & Yr. Round
  • Waterfront rentals, water view rentals and rentals with pools
  • All styles of Shelter Island rentals, from secluded compounds to rustic cottages
  • Shelter Island summer rentals with all the amenities you need including pools and fully furnished kitchens, beds and baths