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
Harbour House Inn
725 North State Road Cheshire MA
The price is AU$386 per night from 9 Dec to 10 Dec
AU$386
9 Dec - 10 Dec
includes taxes & fees
9.6/10 Exceptional! (39 reviews)
Great place, great hosts, lovely experience. Would go back 100x.
Reviewed on 14 Nov 2025
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
The price is AU$156 per night from 9 Dec to 10 Dec
AU$156
9 Dec - 10 Dec
includes taxes & fees
8.6/10 Excellent! (2,146 reviews)
Nice place to stay, off season. Price was very reasonable. Room was comfortable, (1st floor, Building 5), entire building was very quiet, hardly anyone on the property. Nice amenities, but we only walked through, did not use (pool, locker rooms, hot tub, fire pit). Room was nicely appointed and comfortable. ...
Reviewed on 22 Nov 2025
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (766 reviews)
When we are out in Pittsfield we always stay at the BML. The rooms are spacious, clean, and comfortable. For the price of a hotel room, you get a small condo. The staff is always friendly and helpful. Stay there, you won't regret it.
Reviewed on 26 Nov 2025
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.
