Wander Inn
6 guests
2 bedrooms
Southold, New York
Wander Inn is an architect-renovated ranch in a beautiful setting. Built in the sixties, this home is made for relaxation and indulgence.
Shelter Island Guest Houses
We selected the 914 homes worth renting in this location
Home spotlights in Shelter Island
Long Island Iced Tea
8 guests
3 bedrooms
Remsenburg, Remsenburg-Speonk
Not too far from the bright lights of New York City, this striking and stylish home sits near the beaches of Westhampton and among the protected marshlands of Long Island. The house itself is a modern twist on the traditional clapboard homes the area is famous for, with wraparound decks looking into the treetops to the rear and plenty of sliding doors allowing the indoors to seamlessly slip into the outdoor space.
Technicolour Dreamland
6 guests
3 bedrooms
Northwest Harbor, East Hampton
This colourful Hamptons home has a laid back, friendly feel that would be perfect for a group of friends or family. In a quiet part of the Northwest Woods area of East Hampton, the house is surrounded by trees which guarantees peace, quiet and privacy to enjoy your trip.
Hampton Set
6 guests
4 bedrooms
Northwest Harbor, East Hampton
Live your best East Hampton life at this light-filled, mid-century architectural gem, just a seven-minute drive from the beach. With its private pool and hot tub, grassy lawns backed by juniper trees for post-pool games (table tennis, anyone?
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Looking for guesthouse style accommodation in Shelter Island? You've come to the right place: Our homes come fully furnished with well-equipped kitchens, toiletries in bathrooms & all linen included. Book today and enjoy a short or extended stay in the best guesthouse style accommodation that Shelter Island has to offer. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.
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