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Vacation rentals in Cheshire

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Top-rated vacation rentals in Cheshire

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

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
Rental unit in Lanesborough / Hancock
"Bohemian Nest" sweet, spotless, spacious 1br apt
"Bohemian Nest" is conveniently located in the heart of the Berkshires in an historic 1820 home. Williamstown and Mass MoCa are up the road, Lenox is to the south, and Mount Greylock is around the corner. It's a fully equipped 500 sq. ft. apartment, upstairs, light, airy, charming and immaculate. A brand-new queen-size Casper mattress, fully-equipped kitchen, air conditioning, electric heat, and off-street parking are at the ready to make your visit as comfortable as it is memorable.
$88 per night
Rental unit in Adams
Mountain Living, 1-bedroom unit, outdoor hot-tub
Relax & enjoy nature in this tranquil, 1 bedroom unit down the block from Mt. Greylock, highest mountain in MA! 2 minutes away from hiking trails, 10 minutes away from Mass Moca, 25 minutes away from Jiminy Peak ski resort. Enjoy MT Views, and jump in the outdoor jacuzzi right outside your bedroom. WiFi, AC, your own thermostat & TV. The suite you’ll be staying in is directly attached but separate access from the main house. Military and HCP discounts
$95 per night

Stay near Cheshire's top sights

Photo of Whitney's Farm Market & Garden Center
Whitney's Farm Market & Garden Center20 locals recommend
Photo of Mount Greylock State Reservation
Mount Greylock State Reservation24 locals recommend
Photo of Berkshire Outfitters
Berkshire Outfitters4 locals recommend

Other great vacation rentals in Cheshire

Private room in Dalton
Dalton in the Beautiful Berkshires
$65 per night
Rental unit in Lanesborough
Lovely studio minutes from Jiminy Peak
$111 per night
Guesthouse in Adams
Convenience & style in downtown Adams
$100 per night
Guest suite in Hancock
Cozy apartment near Jiminy Peak
$80 per night
Cottage in Hinsdale
Cozy 1BR Cottage with Loft, Patio, and Fire Pit
$99 per night
Private room in Williamstown
$75 per night
Guest suite in Adams
Quaint Suite in Center of Adams
$110 per night
Home in Adams
No Cleaning Fee-Mountain View Hideaway
$160 per night
Rental unit in Williamstown
Downtown | Waterfront | Walk to Shops | Studio
$130 per night
Rental unit in North Adams
Steps to MoCA, SKI nearby: 2bd + SAUNA!
$112 per night
Private room in Lanesborough
1bed rm. skier’s bliss 2 miles only 1 rd to slopes
$100 per night
Cottage in Lanesborough
Wildlife Lakeside Cottage
$161 per night