Vacation rentals in Cherry Plain

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Top-rated vacation rentals in Cherry Plain

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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 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.

$88 per night

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Rental unit in New Lebanon

Folk Art Studio: 1-bedroom near the Berkshires

Peaceful and characterful 1-bedroom apartment that's part of a Victorian house from 1830. We call it the Folk Art Studio because it has a primitive, imperfect, colorful feel, but is also very comfortable and quite modern. Fully stocked kitchen, bath with tub, washer-dryer, work space, good wifi, lovely living room, round dining table, and private garden access. It's on a quiet country road that offers historic houses and fantastic access to the Berkshires.

$99 per night

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Rental unit in Petersburg

The Beer Diviner Brewery Apartment

Whole upstairs space 14 x 28 feet, small bathroom with claw foot tub and shower, twin and a full size bed, High def TV with blu ray movies, private deck, small fridge and microwave, complimentary tea and coffee (no breakfast). Complimentary pint downstairs at the brewery and taproom. Located in a private setting in a hollow in the Taconic Mountains

$75 per night