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.
The Whaler's Cottage
5 guests
3 bedrooms
Sag Harbor, Southampton
Dating back to the eighteenth century, it’s safe to say that The Whaler’s Cottage is steeped in history. It has a wonderful garden with lots of room for relaxing, and the interiors are stunning.
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?
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.
Explore the 122 most perfect homes in our collection
Discover a selection of the best coastal homes in Shelter Island. Plum Guide’s homes come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Book your next getaway today and enjoy a short or extended stay in the best coastal homes in Shelter Island. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.
