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
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is AU$220 per night from 22 June to 23 June
AU$220
22 June - 23 June
includes taxes & fees
9/10 Wonderful! (961 reviews)
"Water pressure in shower overwhelmingly strong"
Reviewed on 2 June 2026
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
The price is AU$212 per night from 17 June to 18 June
AU$212
17 June - 18 June
includes taxes & fees
8.8/10 Excellent! (2,388 reviews)
"While traveling in the area for summer we found Vacation Village. Great jump off point, great amenities, helpful staff, nice set up inside the condo, pots, pans, utensils, glassware, other cooking utensils in good shape. Private decks are a nice touch. Best bargain in the area by far!!! Will be ..."
Reviewed on 1 June 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
The price is AU$167 per night from 11 June to 12 June
AU$167
11 June - 12 June
includes taxes & fees
9/10 Wonderful! (969 reviews)
"I loved the funky vibe of this place. It was also very cozy."
Reviewed on 2 June 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.
