Photo by Ed Gaffny
Plan, book, travel with confidence
Better together
Save up to ₩9,995 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
Cheshire Hotel Deals
Life House Berkshires
194 Pittsfield Rd, Lenox, MA
The price is ₩163,740 per night from Jun 6 to Jun 7
₩163,740
per night
Jun 6 - Jun 7
9/10 Wonderful! (252 reviews)
"Terrific renovation of two story motel. Great bedding and toiletries. Everything has a curated retro-hipster look. Spacious shower and bathroom, closet space, robes, plenty of charging outlets and a big TV, great if you use Apple. The only downside is noisy, bulky air conditioner. Be sure to ask ..."
Reviewed on May 28, 2024
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd, Lenox, MA
The price is ₩174,269 per night from Jun 17 to Jun 18
₩174,269
per night
Jun 17 - Jun 18
9/10 Wonderful! (1,005 reviews)
Great place to stay
"The staff was super friendly. The room was clean and I had no issues at all."
Reviewed on Jun 4, 2024
The Red Lion Inn
30 Main Street, Stockbridge, MA
Fully refundableReserve now, pay when you stay
The price is ₩245,216 per night from Jun 17 to Jun 18
₩245,216
per night
Jun 17 - Jun 18
8.8/10 Excellent! (889 reviews)
"Always a great HISTORIC INN"
Reviewed on Jun 2, 2024
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.
Frequently asked questions
Discover the most popular places to visit in Cheshire
St Mary's of the Assumption Church
5/5(1 review)
Learn about the local history of Cheshire with a stop at St Mary's of the Assumption Church. Discover the area's mountain views, or seek out its ski slopes.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.