Vacation rentals in Stephentown

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Top-rated vacation rentals in Stephentown

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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

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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

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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