Vacation rentals in Cheshire

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Top-rated vacation rentals in Cheshire

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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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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

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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

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