Cheshire Holidays
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Top hotels in Cheshire
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is €136 per night from 17 Jun to 18 Jun
€136
17 Jun - 18 Jun
includes taxes & fees
9/10 Wonderful! (962 reviews)
"We love the Bershire Mountain Lodge. We've stayed here five other times but this time we do have a few very minor negatives. 1) The cabinet door under the kitchenette sink had a loose hinge. We messaged the staff and requested that they wait until after we checked out to repair the hinge. We hope ..."
Reviewed on 4 Jun 2026
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
The price is €124 per night from 10 Jun to 11 Jun
€124
10 Jun - 11 Jun
includes taxes & fees
8.8/10 Excellent! (2,389 reviews)
"Great place just listed again for four more nights"
Reviewed on 3 Jun 2026
The Yankee Inn
461 Pittsfield Rd Lenox MA
The price is €107 per night from 16 Jun to 17 Jun
€107
16 Jun - 17 Jun
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
"Beautiful and well maintained and close to shipping and food"
Reviewed on 29 May 2026
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.
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