Shelter Island Homes for Five People

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.

Swan's Nest

• 7 guests

• 4 bedrooms

Bridgehampton, Southampton

You don't even need to step out of this home to take in the view of Sam’s Creek and Mecox Bay, with the sea stretching out in the distance. At this cottage by the water, built up on stilts, you’ll be able to watch it all from the comfort of home.

Venus In Furs

• 6 guests

• 3 bedrooms

Hudson, Columbia County

A grand townhouse in the middle of Hudson, Venus In Furs is not only a great place for exploring the Catskills and the Hudson Valley, but it’s also a destination in its own right. Whether sinking into the plush Chesterfield, or spending long evenings around the fire pit, you have plenty of options when it comes to relaxation.