Ahoy There
8 guests
4 bedrooms
Shelter Island, The Hamptons
This Hamptons home does island life the modern way. In the mornings, hit up the local farmers’ markets and seafood shops.
Shelter Island Homes for a Watersports Holiday
We selected the 930 homes worth renting in this location
Home spotlights in Shelter Island
Villa Menantic
8 guests
4 bedrooms
Shelter Island Heights, Shelter Island
Set across seven private acres on Shelter Island’s Menantic Peninsula, this waterside property epitomises tranquillity. Wake up to views on one of the home's two private balconies, before whipping up breakfast in the state-of-the-art kitchen and sipping your morning coffee as you paddle in the sea.
Long Point
8 guests
4 bedrooms
Noyack, Southampton
Set within an acre of lush green grounds, this seriously charming home is just a twenty-minute drive from the centre of Sag Harbour - undoubtedly one of New York State's best-kept secrets. This centuries-old seaside village may be known as one of the most family-friendly places in the Hamptons, but its strictly adults-only activities include a visit to the nearby Wölffer Estate vineyards to sample their famed rosé cider.
Borne Back
6 guests
3 bedrooms
Northwest Harbor, East Hampton
Just steps away from a private community beach, Borne Back was designed by its architect owner to provide a comfortable contemporary home in a perfectly quiet spot in the Hamptons. On a full acre plot next to Gardiner's Bay, it's surrounded by tall trees.
We selected the top 3% holiday homes in Shelter Island Homes for a Watersports Holiday
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Find the best homes for a watersports holiday in Shelter Island. Every one of our properties has been meticulously vetted by our Plum Guide experts, so you don't have to worry about anything, from the WiFi speed to water pressure. All of our homes come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Arrange your getaway today, and stay in one of the best homes for a watersports holiday in Shelter Island.
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