Search Inns in Cheshire from CA $139

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Our top choices for Cheshire inns

"Big rooms, very friendly staff and great pizza!"

CA $173 total

includes taxes & fees

Aug 21 - Aug 22

"I loved the pool and the wonderful view from the pool. I felt very safe here and there was an overall sense of being welcomed."

CA $187 total

includes taxes & fees

Sep 7 - Sep 8

"Near hiking for Mt. Greylock and the Appalachian Trail. Nice walking area close by at Lamb's Hill. Clean Older mattress, was OK, but could feel springs a little. If you like a tub, it is tiny. The shower is OK"

CA $156 total

includes taxes & fees

Sep 1 - Sep 2

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Top Cheshire Hotel Reviews

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent

"I wish I had known about this place when my kids were young. Perfect family, or adult only spot to unwind and relax in the mountains."

Berkshires Untold

10/10 Excellent

"We loved everything! Josh was great at check in and with recommendations. Nick was truly fabulous bartending and giving us helpful suggestions and tips. Aurora was extremely helpful as well. 5 stat hotel in a great location with an awesome bar and restaurant. Hamburgers were off the chart. Thank you!!! We most definitely will be back!"