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.

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

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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

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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

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