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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
![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
The price is NZ$215 per night from 25 Jun to 26 Jun
NZ$215
per night
25 Jun - 26 Jun
9/10 Wonderful! (1,000 reviews)
Pleasantly surprised
"We had a good experience here! The staff was AWESOME! They were very helpful in checking in and gave us good info. They have a bar but it was not open during the times we were in and out. The breakfast was good and we enjoyed the omelet. Its only on the weekend--wish it was every day! The pool was ..."
Reviewed on 15 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
The price is NZ$271 per night from 23 Jun to 24 Jun
NZ$271
per night
23 Jun - 24 Jun
8.4/10 Very Good! (930 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
![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
The price is NZ$216 per night from 25 Jun to 26 Jun
NZ$216
per night
25 Jun - 26 Jun
9/10 Wonderful! (261 reviews)
Comfy & Pretty!
"Loved my stay! “Front Desk” Team was so friendly and warm - Bobby, Alex, Chris. Room was clean and comfy and space is really pretty and well-done"
Reviewed on 17 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
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.