Cheshire Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to Rp173.195 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Cheshire
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
The price is Rp1.755.879 per night from 24 Feb to 25 Feb
Rp1.755.879
Rp2.146.577 total
24 Feb - 25 Feb
includes taxes & fees
8.8/10 Excellent! (2,261 reviews)
Clean room. Spacious.
Reviewed on 22 Feb 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is Rp1.924.978 per night from 24 Feb to 25 Feb
Rp1.924.978
Rp2.527.478 total
24 Feb - 25 Feb
includes taxes & fees
9/10 Wonderful! (860 reviews)
Room was spotless! Kitchen was so helpful. Pool was a major hit with the kids and was warm even though it was February! They spent hours in the pool and outdoor hot tub. Will definitely stay here again!
Reviewed on 23 Feb 2026
The Williams Inn
101 Spring Street Williamstown MA
Fully refundableReserve now, pay when you stay
The price is Rp3.176.633 per night from 24 Feb to 25 Feb
Rp3.176.633
Rp3.548.299 total
24 Feb - 25 Feb
includes taxes & fees
9.6/10 Exceptional! (579 reviews)
This hotel is clean, modernized and close to Williamstown POI.
Reviewed on 22 Feb 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.
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.
