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Berkshire Mountain Lodge
These are all 1 bedroom suites. There was plenty of room in kitchen cupboards for our groceries. The kitchen was well supplied with cooking utensils, dishes and glassware. The location is excellent with several grocery stores and restaurants close by. Everything was perfect except for the height ...
Reviewed on May 11, 2026
Berkshires Untold
Quiet, nice staff, nice place
Reviewed on May 11, 2026
Vacation Village in the Berkshires
Everything was great!
Reviewed on May 10, 2026
Hotel Downstreet, an Ascend Collection Hotel
Super clean, great coffee spread for breakfast. I really enjoyed my stay.
Reviewed on May 9, 2026
The Red Lion Inn
Lovely and historic property. Friendly staff and very comfortable room. Dinner and breakfast were wonderful. We are repeat visitors.
Reviewed on May 11, 2026
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
This was like staying in a two bedroom walk up in NYC only sooooo much bigger and better! We were pleasantly surprised at the spaciousness of our Room! (The presidential suite). Everything was clean and tidy. Very pleasant decor. While there was not a place to get coffee down in the lobby area, there ...
Reviewed on May 4, 2026
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Clean room and great bedding. If you’re not into specific cuisine, you have to go to town for dinner options.
Reviewed on May 11, 2026
Hampton Inn & Suites Berkshires-Lenox
The room had very inadequate seating in the room. Only 2 small chairs and no couch. Not comfortable. Other than that it was OK.
Reviewed on May 10, 2026
The Williams Inn
Staff was very helpful. Rooms were great. Unbeatable location for Williamstown (especially if you’re in town for an athletic event at Williams). Really solid breakfast with friendly and attentive wait staff. Only minor complaint is that the WiFi is not great. Other than that it was a perfect ...
Reviewed on May 10, 2026
Hotel On North
It was an absolute pleasure to stay! We enjoyed ourselves and felt very comfortable
Reviewed on May 11, 2026
Courtyard by Marriott Lenox Berkshires
This hotel seemed brand new although built I believe in 2017. It was very clean and well maintained. We enjoyed the outdoor firepit.
Reviewed on May 2, 2026
The Porches Inn at Mass MoCA
We really enjoyed the layout of the property and proximity to MASS MOCA. Hotel was a little loud due to the rooms being in a older houses with wood floors, so we were up a bit earlier than we hoped. Overall we had a nice one night stay.
Reviewed on May 10, 2026
Find cheap hotels in Cheshire
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For you, intrepid voyager, Hotwire has a large selection of the best hotels in Cheshire.
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 1,016 hotels. Choose the one that best catches your trip’s tourist drift.
If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $121. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get great Cheshire hotel deals at the last minute.
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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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