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Vacation rentals in Stephentown

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Top-rated vacation rentals in Stephentown

Guests agree: these stays 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.
$243 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
Vacation home in Stephentown
Quiet, peaceful wooded setting.
In the foothills of the Berkshires and Jiminy Peak. Charming and quaint cities such as Stockbridge and Great Barrington are a convenient 45 minute drive. Also accessible to many wonderful cities in Vermont. Many parks and bike trails are within easy reach. I welcome long term stays up to 28 days .
$95 per night

Other great vacation rentals in Stephentown

Cottage in New Lebanon
The Writer's Cottage
$90 per night
Guest suite in Stephentown
1 Bedroom Farmhouse Suite - 5 Mins to Jiminy Peak
$150 per night
Guest suite in Hancock
Cozy apartment near Jiminy Peak
$80 per night
Cottage in Stephentown
Stone Bridge Cottage, minutes to Berkshires
$185 per night
Rental unit in Lanesborough / Hancock
"Bohemian Nest" sweet, spotless, spacious 1br apt
$88 per night
Rental unit in Canaan
Mountain View Getaway
$94 per night
Rental unit in Lanesborough
Lovely studio minutes from Jiminy Peak
$111 per night
Cottage in New Lebanon
Stylish Working Farm Cottage
$199 per night
Rental unit in New Lebanon
Sunny Duplex at the old boarding house
$119 per night
Farm stay in Pittsfield
Private 2nd floor studio on a working produce farm
$99 per night
Home in Lebanon Springs
Experience Spring in the Berkshire Hills!
$206 per night
Home in New Lebanon
The old sawmill from 1771
$125 per night