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Choose from 998 Cheshire Hotel Deals
Vacation Village in the Berkshires
Hotel Downstreet, an Ascend Collection Hotel
Berkshire Mountain Lodge
"The kitchen was excellently equipped, I had everything I needed. The door to my room was very difficult to open as it was humid and had expanded. I had to do a football tackle to open it from the outside. Everything in the room felt tacky and damp. I had plenty of towels, and the water pressure in ..."
Reviewed on Jul 30, 2026
The Yankee Inn
"I would stay here again for sure. Nice clean room, generous breakfast, pool and hot tub, what’s not to like? Very convenient to Bousquet ski area. Restaurants nearby. Easy drive into either Lenox or Pittsfield."
Reviewed on Jul 28, 2026
Berkshires Untold
"Rooms where rather small, but Adequate. The location was good. Mainly a typical hotel"
Reviewed on Jul 30, 2026
The Red Lion Inn
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
"Super clean, nicely renovated hotel conveniently located in the Berkshires. We loved the pool and hot tub. Room was nice and modern, as was the lobby/breakfast area. Reasonably priced. Thanks for a lovely stay!"
Reviewed on Jul 29, 2026
FairBridge Inn Express
"Stayed for 2 nights. Room was nice and clean, had shampoo, conditioner, soap, hair dryer. Bed was pretty comfortable. Definitely not bad for the price. Would stay here again."
Reviewed on Jul 27, 2026
Howard Johnson by Wyndham Lenox
"Parking was easy and the room was nice. This lodging is my new favorite when I take trips to the Berkshires."
Reviewed on Jul 23, 2026
The Williams Inn
"Hotel was terrific..very clean..restaurant was excellent…very well located for Williams College"
Reviewed on Jul 27, 2026
Jiminy Peak Mountain Resort
"Excellent "get away from it all" vibe on this little mountain resort. The drive and area is wooded and beautiful. The staff is AMAZING! Helpful, friendly, warm and welcoming. The rooms were cute and clean. Maybe a little dated and worn, but for the price they are perfect!! The pool was a bit small, ..."
Reviewed on Jul 28, 2026
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Find cheap hotels in Cheshire
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Choosing the right hotel in Massachusetts has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of Cheshire’s 998 hotels. Choose the one that best catches your trip’s tourist drift.
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Frequently Asked Questions About Cheshire hotels
Where can I find the best last-minute travel deals?
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How many hotels are there in Cheshire?
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- Hotels near St Mary's of the Assumption Church
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- Hotels near Jiminy Peak Mountain Resort
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- Hotels near Massachusetts Museum of Contemporary Art
- Hotels near Williams College
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