Dappled Sunlight
8 guests
4 bedrooms
Northwest Harbor, East Hampton
Make like a New Yorker and escape to the famous Hamptons. This home has everything you could need for an effortless, laidback break from the city.
Shelter Island Luxury Rentals
We selected the 108 homes worth renting in this location
Home spotlights in Shelter Island
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.
Sunset Heart
8 guests
4 bedrooms
Bellport, Brookhaven
This Martha’s Vineyard-inspired house in nestled in the village of Bellport. You can enjoy leisurely strolls to the nearest restaurants and you’ll have access to a private beach if your stay is longer than a week.
High Tea & Hedgerows
8 guests
4 bedrooms
Pawling, New York
This home sits pretty as an English manor in the countryside of upstate New York, a ten-minute drive from the picturesque town of Pawling. Grecian-style columns greet you on arrival and the striking white facade glows against the verdant green gardens – it sits on 18 acres of land.
We selected the top 3% holiday homes in Shelter Island Luxury Rentals
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A handpicked selection of the best luxury homes in Shelter Island, as chosen by the experts who've visited and vetted thousands of the city's homes. Luxurious interiors, sumptuous bedrooms and prime city centre locations. Available for short and extended stays.
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