When In Bloom
6 guests
3 bedrooms
Southampton, The Hamptons
This Hamptons house sits on seven acres of lush greenery, with plenty of space for both kids and adults to enjoy. Old meets new inside, with patterned rugs, antique furniture and an imposing fireplace, along with a slick kitchen complete with coffee grinder and juicer.
Kennedies
9 guests
4 bedrooms
North Sea, Southampton
An idyllic escape for all the family, this waterfront home sits in the hamlet of North Sea, part of larger Southhampton, and within an easy drive of a wide selection of restaurants, boutique shops and beautiful beaches. Whether you're here for a weekend or a longer stay, you'll immediately feel relaxed in this quiet spot, surrounded by nature.
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.
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.
Explore the 930 most perfect homes in our collection
Discover the genuine quality of our collection of Vacation Rentals for Thanksgiving in Shelter Island. There's no time for average stays on our watch, so only the top 3% of homes are accepted into our exclusive range at the time of their addition. Every Plum Guide property is put through multiple rounds of vigorous testing, with everything from shower pressure to a home's design closely inspected. For your convenience, every rental will also come fully furnished, with a well-equipped kitchen, all linen, and essential bathroom toiletries included. Reserve your stay in a luxury Thanksgiving Vacation Rental in Shelter Island today, and celebrate the occasion the only way you know how - in true style. Call on the help of our tireless team of experts, who enjoy nothing more than pairing you up with your dream home.
