The Berkshires Cheap Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Photo courtesy of Berkshire Visitors Bureau
- Plan, book, travel with confidence
Better together
Save up to NZ$616 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 Cheap The Berkshires Hotels
Pleasant Valley Motel West Stockbridge
42 Stockbridge Rd, West Stockbridge, MA
Stay at this motel in West Stockbridge. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the clean rooms in our reviews. Popular attractions ...
6.8/10 (995 reviews)
Kathleen from Coventry
"We always enjoy our stay here because of its location to our venue, eating options and the customer friendly owners. It is a bit dated in its interior design, but a clean room wih a clean bed and working shower is our goal. They deliver."
Reviewed on 18 Aug. 2025
Wagon Wheel Inn
484 Pittsfield Rd, PO Box 808, Lenox, MA
Stay at this motel in Lenox. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood ...
7/10 Good! (624 reviews)
"And I mean the David Lynch as a compliment."
Reviewed on 14 Aug. 2025
Lantern House Motel
256 Stockbridge Road, Great Barrington, MA
Stay at this motel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Housatonic River and Lake Mansfield Park are located ...
Avoid staying here if you can.
"The fact that they require a vaccine card should be mentioned in their Hotels.com profile. Luckily for me I had it in my car. I don't mind if some hotel owners want to require it, but it should be pretty clearly stated. The owner told me that I didn't need to use the air conditioner, that I should ..."
Reviewed on 22 Nov. 2021
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.