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Vacation rentals in Cherry Plain

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Top-rated vacation rentals in Cherry Plain

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

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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Guest suite in Williamstown
Berkshire Guest Suite
Welcome to our guest suite in the beautiful Northern Berkshires, home to many great cultural venues, including The Clark, Williamstown Theatre Festival and Mass MoCA. The newly updated private suite offers a queen pillow-top mattress, bathroom with stall shower, coffee bar and an outdoor seating area with mountain views. Located in a quiet neighborhood at the base of Mt. Greylock, we are a short walk to a local farm stand, and a few minutes drive to downtown Williamstown and North Adams.
$85 per night
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Guest suite in Hancock
Cozy apartment near Jiminy Peak
Two cozy bedrooms with an efficient kitchen make this a great weekend getaway for 2 adults or family of 3 to use as a base to explore both north and south Berkshire county in every season. About a mile from Jiminy Peak Ski Resort, less than 5 minutes to Bloom Meadows, 15 minutes to both Williamstown and Pittsfield, and 30 minutes to Mass MoCA, the quiet, wooded mountainside surroundings let you enjoy nature at its finest while easily getting to the area's many cultural attractions.
$80 per night
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Other great vacation rentals in Cherry Plain

Vacation home in Williamstown
Lovely 1 BR studio - winter wonderland location
$150 per night
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Cottage in Williamstown
Cute Cozy Comfy Cottage in the Berkshires
$139 per night
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Cottage in Williamstown
1840s Schoolhouse near Jiminy, skiing, MassMoCA
$195 per night
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Rental unit in Williamstown
Quiet Williamstown Apartment close to downtown.
$99 per night
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Private room in Williamstown
Robin's
$75 per night
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Cottage in Hancock
Berkshire Cottage Queen Bd-Jiminy Peak 3 mi
$159 per night
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Home in Pownal
Cozy Vermont mini-house
$205 per night
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Rental unit in Williamstown
Cozy barn apartment on the river
$136 per night
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Rental unit in Lanesborough / Hancock
"Bohemian Nest" sweet, spotless, spacious 1br apt
$88 per night
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Rental unit in Lanesborough
Lovely studio minutes from Jiminy Peak
$111 per night
Cottage in New Lebanon
The Writer's Cottage
$90 per night
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Cabin in Stephentown
Cabin in the woods w cedar Hot Tub + private pond
$239 per night
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