
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.
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.
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.
Magic in The Hamptons
10 guests
5 bedrooms
Springs, East Hampton
This beautiful home is set within dense woodland on the northern East Hampton Coast, just two blocks from a private beach looking out over Gardiners Bay. Inside, there are beautiful hardwood floors, a cosy fireplace for cool evenings and cathedral-like ceilings over the dining area.
Sunflower Summer
7 guests
3 bedrooms
Springs, East Hampton
Look out for artists, poets and musicians in the area around this home – it’s located in Springs, arguably the coolest town in the Hamptons. In the past, it’s played host to visionaries like Jackson Pollock and Lee Krasner, Willem de Kooning, Kurt Vonnegut, and John Steinbeck.
Explore the 84 most perfect homes in our collection
Discover our curated collection of luxury holiday Cottages in Shelter Island. We painstakingly review all homes available in a destination and accept only the top 3% to ensure quality our guests can trust. Each of the Shelter Island Cottages in our collection comes fully furnished with essential bathroom toiletries, expertly-equipped kitchens and all linens included. Book your dream stay today and should you need some help, our friendly team of experts are on hand to help plan your perfect Cottage break.