Columbia County 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.

The Rainbow Bird

• 8 guests

• 4 bedrooms

Woodbury, Litchfield County

This country home is located on 6 acres of private land, so there’s plenty of outdoor space to enjoy here. We love the scenic views from the terrace, where you’ll have a front row seat to watch the sun set behind the surrounding hills and a fire pit to keep you warm on chilly evenings.

Dahlia Darling

• 10 guests

• 5 bedrooms

Sullivan County, Bethel

Indulge yourself in the natural world at this sun-drenched home, with plenty of space for friends and family indoors and out. You'll find toys and games along with free children's sledges for enjoying the snow, and kids will love the bunk beds.