Which Way The River
11 guests
4 bedrooms
Shandaken, New York
Have you ever wanted your very own slice of the Catskills? Of course, you have.
Middletown Ski In Ski Out Rentals
We selected the 34 homes worth renting in this location
Home spotlights in Middletown
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.
Dahlia Darling
10 guests
5 bedrooms
Bethel, New York
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.
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 Middletown 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 Middletown? 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 Middletown. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.
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