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 Hamptons Ski In Ski Out Rentals
We selected the 34 homes worth renting in this location
Home spotlights in The Hamptons
River Song
10 guests
5 bedrooms
Dalton, Berkshire County
It’s no wonder why a multitude of actors, composers, and artists have hideaways in the Berkshires. This classic Berkshires home, originally built as a schoolhouse in 1866, is steeped in history and rural charm.
Art & Nature
6 guests
4 bedrooms
Cragsmoor, Wawarsing
This home's architecture, interiors and colourful prints all share a mid-century modern style, but its woodland surroundings are more Hansel and Gretel than Gilbert and George. In a tiny hamlet in upstate New York, it’s surrounded by mountains, lakes and forest – great for skiers, hikers and wild swimmers alike.
The Masterplan
10 guests
4 bedrooms
Tunkhannock Township, Monroe County
Just a two-hour drive from New York City, this home in the Poconos is more like a private resort, with an impressive list of amenities and all kinds of entertainment options for a large group. Set less than ten minutes away from scenic Lake Harmony by car, and close to various ski resorts like Jack Frost and Big Boulder Mountain, there are shops and restaurants within a few minutes drive, along with nearby golf courses and a water park.
We selected the top 3% holiday homes in The Hamptons Ski In Ski Out Rentals
Explore the 34 most perfect homes in our collection
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Frequently asked questions
Planning a winter holiday and looking for a ski-in ski-out rental in The Hamptons? You've come to the right place: Our homes come fully furnished with well-equipped kitchens, toiletries in bathrooms & all linen included. Book today and enjoy a short or extended stay in one of the best ski-in ski-out rentals in The Hamptons. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.
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