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 S$153 per night from 24 May to 25 May
S$153
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 S$142 per night from 25 May to 26 May
S$142
25 May - 26 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 S$136 per night from 11 May to 12 May
S$136
11 May - 12 May
includes taxes & fees
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
