Cheshire Packages (Flight + Hotel)
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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 ฿2,856 per night from 31 May to 1 Jun
฿2,856
฿3,918 total
31 May - 1 Jun
includes taxes & fees
9/10 Wonderful! (943 reviews)
"The rooms were so spacious, with a great kitchen full of dishware to use. The Staff were so kind, helpful and knowledgeable."
Reviewed on 21 May 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is ฿4,071 per night from 27 May to 28 May
฿4,071
฿4,547 total
27 May - 28 May
includes taxes & fees
9/10 Wonderful! (952 reviews)
"all very good for our 1 night stay!!"
Reviewed on 20 May 2026
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
The price is ฿2,808 per night from 25 May to 26 May
฿2,808
฿3,494 total
25 May - 26 May
includes taxes & fees
8.8/10 Excellent! (2,362 reviews)
"Nice staff, nice room and facilities. Having stayed there several times happily and will be back again in June. Thanks."
Reviewed on 22 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.
