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Vacation rentals in Cheshire

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Cheshire

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

Guesthouse in Adams
Convenience & style in downtown Adams
This apartment has everything you need for a nice getaway in the northern Berkshires. It is within walking distance from downtown Adams and Ashwilltook Rail Trail, 12 min drive from MASS MoCA, 5 min drive from Greylock Glen, and 20 min drive from Williamstown. It was renovated in 2021 to provide a turn-key experience, great amenities, and modern furnishing for both short-term & long-term stays. The 750 sqft apartment has a fully stocked kitchen, internet TV, multiple desks, washer, and dryer.
$101 per night
Rental unit in Lanesborough
Cozy Rustic Suite in 18th c. Berkshire Farmhouse
This cozy rustic studio is located at the base of Mount Greylock and a 6 minute drive from Jiminy Peak ski resort. Built in the 1700’s, this centuries old farmhouse has since been converted into four separate cute suites. Newly updated kitchen, bathroom and furniture. Enjoy exploring the sprawling 19 acre property you will be staying on which includes seasonal flower fields, thousands of berry bushes, fruit trees, creek, and walking trails full of wildlife. Follow us on IG @SecondDropFarm
$111 per night
Cabin in Cheshire
Private Paradise in the Berkshires
Your own private and romantic getaway behind a small orchard. A sweet running brook and outdoor shower! A short drive to all Berkshire cultural events -- Tanglewood, Jacob's Pillow, theatre festivals and more. Great dining nearby. Perfect for 2! Under COVID-19 regulations in Massachusetts, I am required to allow at least 24 hours between guests. It's a drag, but it is intended to keep us all healthy! Please forgive any inconveniences this might create in your trip plans.
$155 per night

Stay near Cheshire's top sights

Photo of Mount Greylock State Reservation
Mount Greylock State Reservation24 locals recommend
Photo of Whitney's Farm Market & Garden Center
Whitney's Farm Market & Garden Center20 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
$75 per night
Guest suite in Adams
Quaint Suite in Center of Adams
$130 per night
Rental unit in Adams
Mountain Living, 1-bedroom unit, outdoor hot-tub
$113 per night
Private room in Lanesborough
1bed rm. skier’s bliss 2 miles only 1 rd to slopes
$100 per night
Guest suite in Dalton
Berkshires getaway: nature, culture & relaxation
$161 per night
Private room in Williamstown
$75 per night
Guest suite in Williamstown
Berkshire Guest Suite
$87 per night
Rental unit in Lanesborough / Hancock
"Bohemian Nest" sweet, spotless, spacious 1br apt
$92 per night
Home in Cheshire
Berkshires Lakefront Retreat on 4 Private Acres
$423 per night
Home in Cheshire
Large Secluded Berkshire Home
$233 per night
Rental unit in North Adams
Steps to MoCA, 2bd + SAUNA!
$146 per night
Rental unit in Williamstown
New Studio In Town, By the Water
$136 per night

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