Cheshire, MA Chalets

Check prices for these dates

Next weekend

24 Muh. - 26 Muh.

In two weeks

31 Muh. - 2 Saf.

In one month

14 Saf. - 16 Saf.

In two months

14 Rab. I - 16 Rab. I

Compare 6 Chalets in Cheshire with updated reviews, rates, and availability.

"We were all very rested and relaxed. We enjoyed the beautiful spaces to sit and enjoy each other’s company. The chalet, flowers and setting made a terrific base to come and go from as we celebrated a family wedding."

"The location was great. Very peaceful. Not far from Lee, Lenox or Great Barrington. The house was very cute and as described. Will absolutely stay again. "

garden view of the back of the cabin, with the deck

"We really enjoyed our stay at this adorable A frame home. The home was a quick drive to tanglewood and the views were beautiful. The owner was very communicative and prompt with answering any questions. "

"We had a wonderful time - delightfully snowy and the house was quiet and cozy."

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Other property types in Cheshire

"I enjoyed my stay here, Thanksgiving weekend, 1st snow, picturesque, comfortable Kitchen is adequate, bathroom had a spa tub that helped take the chill out, heat was on when we entered Laundry machines are available (we did not use them though) We did not try the amenities, pretty much stayed in and enjoyed cooking a small holiday meal in this beautiful setting One thing of note- television in bedroom was not working"

SAR 810 total

includes taxes & fees

22 Jan - 23 Jan

"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...

"The house was great with plenty to do in the area. It was warm, comfortable, and just what we were looking for a quick weekend away. Would definitely return.Thanks,-Mike"

Recent reviews of Cheshire hotels

5/5 Excellent

"I enjoyed my stay here, Thanksgiving weekend, 1st snow, picturesque, comfortable Kitchen is adequate, bathroom had a spa tub that helped take the chill out, heat was on when we entered Laundry machines are available (we did not use them though) We did not try the amenities, pretty much stayed in and enjoyed cooking a small holiday meal in this beautiful setting One thing of note- television in bedroom was not working"

A verified traveler stayed at Vacation Village in the Berkshires

Posted 1 day ago

5/5 Excellent

"You feel like a treasured friend or a cherished family member at The Cornell Inn … above every other wonderful aspect of the Inn (cleanliness, beautifully appointed suite, comfortable bed, delicious food) the service is impeccable! - warm, welcoming, and friendly! Thank you! We will certainly be back!"

A verified traveler stayed at The Cornell Inn, Lenox

Posted 2 days ago