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Stephentown Center vacation rentals

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Top-rated vacation rentals in Stephentown Center

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Cabin in Stephentown
Cabin in the woods w cedar Hot Tub + private pond
The Hemlock Hideaway is a charming, rustic cabin in the woods designed for rest and relaxation. Guests will journey into simpler times, inspired by antique furnishings that remind them to slow down and unwind during their stay. The cabin is isolated yet only 10 min drive to Jiminy Peak for skiing as well as park and trails for hiking, apple orchards, excellent restaurants and foliage viewings. Cherry Plain State Park, Mount Greylock, Lebanon Speedway, Albany, and Pittsfield are all 25 min max.
$246 per night
Rental unit in Stephentown
2 Bed Berkshire Getaway minutes to Jiminy Peak Ski
Welcome to the historic Stephentown Hotel! The apartment was completely remodeled in 2023. We are located minutes away from Jiminy Peak Ski Resort in the world famous Berkshire Mountains! Right on the NY / MASS border in beautiful Stephentown. Surrounded by nature and serenity. Beautiful 2 bedroom apartment with a private entrance, fire pit, BBQ and old fashion popcorn machine on site! Every stay includes water bottles, granola bars, oatmeal packets, coffee and tea! Parking right in front.
$81 per night
Cottage in New Lebanon
The Writer's Cottage
The Writer's Cottage is a tiny white house on a country road; vintage, complete, and inspiring. Built in the nineteenth century, it's perfect for a solo traveler or a pair of travelers exploring the Berkshires and the Hudson Valley. If you like rustic buildings, you'll be a fan of the cottage; it's an incredibly cozy time warp. Queen bed and living quarters downstairs; airy loft up a narrow set of enclosed stairs. There's an orchard and lawn with grill, hammock and table.
$90 per night

Other great vacation rentals in Stephentown Center

Cottage in Stephentown Center
Ski Season, The Only Stephentown on Earth!
$175 per night
Vacation home in Stephentown
Quiet, peaceful wooded setting.
$95 per night
Guest suite in Hancock
Cozy apartment near Jiminy Peak
$80 per night
Rental unit in Canaan
Mountain View Getaway
$96 per night
Cottage in Stephentown
Stone Bridge Cottage, minutes to Berkshires
$185 per night
Tiny home in Chatham
Blush: A TINY Glam Pad w/private spa & cozy loft
$175 per night
Home in Stephentown
Dog Friendly Studio
$175 per night
Cottage in New Lebanon
Stylish Working Farm Cottage
$159 per night
Guest suite in Williamstown
Berkshire Guest Suite
$75 per night
Rental unit in Lanesborough / Hancock
"Bohemian Nest" sweet, spotless, spacious 1br apt
$88 per night
Home in Pownal
Cozy Vermont mini-house
$205 per night
Cabin in Canaan
Rustic Barn Studio Apartment
$145 per night