Cheshire Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Ed Gaffny
- Plan, book, travel with confidence
Better together
Save up to AU$703 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
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$428 per night from 14 Oct to 15 Oct
AU$428
14 Oct - 15 Oct
includes taxes & fees
9.6/10 Exceptional! (38 reviews)
"The owner Brandi was outstanding, friendly, she made us fresh homemade breakfast each morning, which the best. Will differently stay there again. Wonderful place and people."
Reviewed on 12 Sept 2025
Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is AU$175 per night from 2 Nov to 3 Nov
AU$175
2 Nov - 3 Nov
includes taxes & fees
8.6/10 Excellent! (2,039 reviews)
"There were a couple of issues withy stay 10/4/26 to 10/5/26. The staff did not answer my text messages sent as they said they were very busy. The room has small insects and flies. It was reported and staff offered to send maintenance to check on the unit. I was moved to another unit 10/5/25 through ..."
Reviewed on 7 Oct 2025
Hotel Downstreet, an Ascend Collection Hotel
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is AU$224 per night from 11 Nov to 12 Nov
AU$224
11 Nov - 12 Nov
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"Super friendly staff, a free coffee bar in the lobby, loads of food and shopping options within walking distance, free on-site parking - what’s not to love! And the room was spotlessly clean and very very comfortable. We love this place!!!"
Reviewed on 9 Oct 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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
