Cheshire Holidays
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Cheshire Holiday
Our pick of the best Cheshire Hotel Deals
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is NZ$202 per night from 24 May to 25 May
NZ$202
24 May - 25 May
includes taxes & fees
9/10 Wonderful! (925 reviews)
Room very spacious and clean. Full kitchen is a great bonus.
Reviewed on 4 May 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is NZ$214 per night from 10 May to 11 May
NZ$214
10 May - 11 May
includes taxes & fees
9/10 Wonderful! (932 reviews)
Easy, comfortable and convenient; rooms and public spaces are nice, modern and stylish updates of modest 60s/70s original motel facilities.
Reviewed on 6 May 2026
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
The price is NZ$180 per night from 19 May to 20 May
NZ$180
19 May - 20 May
includes taxes & fees
8.8/10 Excellent! (2,351 reviews)
I loved my stay at the resort! The view was beautiful, my room was clean, and the staff were nice. I had trouble with my door, and they sent someone quickly to fix it.
Reviewed on 8 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
