Cheshire Holidays
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Your Cheshire Holiday
When you choose a Cheshire holiday package, it's all about letting go and enjoying your getaway to the fullest. Discover the sights and sounds of this vibrant city knowing that everything has been taken care of before you go. Make your trip to Cheshire even more fun by going sightseeing. Mount Greylock, Mount Greylock State Reservation and Wahconah Falls State Park are among the big attractions worth exploring. Stop dreaming and start doing. Browse the wide range of options on Expedia today and put your Cheshire holiday plans into action!
Cheshire Holiday
Cheshire Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 510 |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 24ºC |
Top Sights | Jiminy Peak Mountain Resort, Bousquet Ski Area and Natural Bridge State Park |
Our pick of the best Cheshire Hotel Deals
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
The price is AU$190 per night from 11 Feb to 12 Feb
AU$190
11 Feb - 12 Feb
includes taxes & fees
8.6/10 Excellent! (2,205 reviews)
The amount of space and super comfortable bed was such a pleasure!
Reviewed on 13 Jan 2026
The Williams Inn
101 Spring Street Williamstown MA
Fully refundableReserve now, pay when you stay
The price is AU$311 per night from 25 Jan to 26 Jan
AU$311
25 Jan - 26 Jan
includes taxes & fees
9.6/10 Exceptional! (561 reviews)
Accommodating staff!
Reviewed on 14 Jan 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Fully refundable
The price is AU$164 per night from 23 Jan to 24 Jan
AU$164
23 Jan - 24 Jan
includes taxes & fees
8/10 Very Good! (1,000 reviews)
Staff was very courteous and rooms clean.
Reviewed on 12 Jan 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.
