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Cheshire Holidays
Photo by Ed Gaffny
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Top hotels in Cheshire
![Life House Berkshires](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/967b0257_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Life House Berkshires
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is S$180 per night from 16 Jun to 17 Jun
S$180
per night
16 Jun - 17 Jun
9/10 Wonderful! (260 reviews)
Modern, friendly and clean
"From my kind greeting from Bobby to my checkout in the morning, my stay could not have been better. Clean and up to date rooms, a great bar and friendly staff. Will definitely come back."
Reviewed on 13 Jun,2024
![Hotel Downstreet](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/644e76fa_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Hotel Downstreet
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is S$225 per night from 16 Jun to 17 Jun
S$225
per night
16 Jun - 17 Jun
8.4/10 Very Good! (928 reviews)
"I really liked everything about it"
Reviewed on 10 Jun,2024
![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/96ff6d07_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is S$204 per night from 25 Jun to 26 Jun
S$204
per night
25 Jun - 26 Jun
9/10 Wonderful! (1,000 reviews)
"AC in the room was to noise. Other than that it was all good."
Reviewed on 10 Jun,2024
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Frequently asked questions
Popular places to visit
St Mary's of the Assumption Church
Learn about the local history of Cheshire with a stop at St Mary's of the Assumption Church. Discover the area's mountain views or seek out its ski slopes.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.