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Cheshire Holidays
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Photo by Ed Gaffny
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Our pick of the best Cheshire Hotel Deals
![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 NZ$248 per night from 9 Jul to 10 Jul
NZ$248
per night
9 Jul - 10 Jul
9/10 Wonderful! (273 reviews)
"Very pleasant place to stay rooms and nice and clean. Staff is very nice."
Reviewed on 21 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 NZ$278 per night from 10 Jul to 11 Jul
NZ$278
per night
10 Jul - 11 Jul
8.4/10 Very Good! (931 reviews)
Nifty hotel in a great little town
"The room was clean and distinctive. Everything worked properly. The hotel is perfectly located for accessing anything in town by foot, including MassMOCA and various eateries."
Reviewed on 16 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 NZ$264 per night from 10 Jul to 11 Jul
NZ$264
per night
10 Jul - 11 Jul
9/10 Wonderful! (1,003 reviews)
"Employees were all super friendly, a very clean and pleasant property. There was nothing that I didn’t like about this place"
Reviewed on 22 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.
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Discover the most popular places to visit in Cheshire
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.