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We Have 91 Vacation Rental Offers Available In Shelter Island. Average Price Per Night Is $873.75. Find Your Vacation Home Today.
Enjoy a charming 3 bedroom/2 bath with central AC on an expansive shy acre corner plot located... Read More
Completely renovated and updated 1929 Sear's kit home with beautiful views to Peconic Bay. Swim,... Read More
This home is a water lover’s paradise on sheltered water with easy access to surrounding east end... Read More
Enjoy the best that Shelter Island can offer at this renovated 2 bedroom waterfront gem. Nestled... Read More
Light-filled retreat with 5 sliding glass doors between indoor/outdoor space with heated... Read More
Walk to Beach from this Bright and Comfortable 3 Bedroom / 2 Bath, Expanded Cottage. Weekly... Read More
Stretch out and relax in this well-designed home high on a hill with truly spectacular water... Read More
Score Big at our fabulous Hamptons Cottage where work meets play in style! Settle into this... Read More
Enjoy summer on Shelter Island in this 3 bedroom, 2 bathroom, freshly painted and well equipped... Read More
This family friendly private three-bedroom, two bathroom Silver Beach ranch house is perfect for... Read More
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