Photo by Ed Gaffny
Plan, book, travel with confidence
Better together
Save up to ฿3,170 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
Top hotels in Cheshire
Life House Berkshires
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is ฿4,368 per night from 9 Jun to 10 Jun
฿4,368
per night
9 Jun - 10 Jun
9/10 Wonderful! (250 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 28 May 2024
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is ฿4,664 per night from 17 Jun to 18 Jun
฿4,664
per night
17 Jun - 18 Jun
9/10 Wonderful! (1,001 reviews)
"This is our go-to spot for short trips to the Berkshires. It's on a busy road, but set back from the street, and it's convenient to everything we need. Good breakfast (better than the one I had a much more expensive hotel in NYC last week) and it's clean and comfortable."
Reviewed on 25 May 2024
The Red Lion Inn
30 Main Street, Stockbridge, MA
Fully refundableReserve now, pay when you stay
The price is ฿7,440 per night from 5 Jun to 6 Jun
฿7,440
per night
5 Jun - 6 Jun
8.8/10 Excellent! (888 reviews)
"Historical. Beautiful night to sit outside. Friendly staff."
Reviewed on 30 May 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
Popular places to visit
St Mary's of the Assumption Church
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.
More trip options
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.