Wander Inn
6 guests
2 bedrooms
Southold, The Hamptons
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 Unique Homes
We selected the 920 homes worth renting in this location
Home spotlights in Shelter Island
Divine Inspiration
10 guests
4 bedrooms
Great Barrington, Lee
There are a lot of adjectives we could throw at this home in The Berkshires; cosy, darling, divine. But none of them really do it justice.
The Great Frontier
4 guests
1 bedrooms
Chatham, New York
Reminiscent of something from a Laura Ingalls Wilder novel, this picturesque cabin is a haven surrounded by peace and quiet and lush woodland. Although you can count on a serene stay here, you’re also just a five-minute drive from the quaint town of Old Chatham where you can find some local amenities, or a ten-minute drive from Chatham Town, which has several excellent restaurants and plenty of charming local 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.
We selected the top 3% holiday homes in Shelter Island Unique Homes
Explore the 920 most perfect homes in our collection
View on map
Check upcoming rates & availability for Shelter Island Unique Homes
Frequently asked questions
Similar destinations
Plum guide offers a handpicked selection of the most unique homes in Shelter Island. Our homes come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Book a short or extended stay and secure the most unique home in Shelter Island for your next getaway. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.
Search Our Collection