Salty Kiss
5 guests
2 bedrooms
Riverhead, The Hamptons
The summer retreat for Manhattan’s wealthy elite, the vibe of the Hamptons couldn’t be further from New York’s chaotic urban sprawl. And if you’re looking for the ultimate in serenity and tranquility, this idyllic beach house is for you.
The Architect's Gallery
10 guests
5 bedrooms
Greene County, Cairo
This 150-year-old Hudson Valley farmhouse sits on 16 acres of land that includes an apple orchard. It’s an idyllic base for those seeking an escape to the peace of the Catskills – though the town of Windham is just a ten-minute drive.
The Old Silo
4 guests
2 bedrooms
Litchfield, Northwest Hills Planning Region
Formerly a grain silo, this extraordinary house is as unique and beautiful as its surroundings. Set on 170 acres of rolling green New England countryside, there are breathtaking views from all sides.
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 80 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.
