
The Berkshires Mountain Holidays
Book a Mountain Hotel + Flight or Car together to unlock savings
Photo by Photo courtesy of Berkshire Visitors Bureau
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Top Mountain The Berkshires Hotels

Jiminy Peak Mountain Resort
37 Corey Rd Hancock MA
Stay at this ski condo in Hancock. Enjoy free parking, 2 restaurants and 2 hot tubs. Our guests praise the property condition in their reviews. Popular attractions ...
8.2/10 Very Good! (987 reviews)
This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the ...
Reviewed on 5 Oct 2025

Club Wyndham Bentley Brook
1 Corey Road Hancock MA
Stay at this ski hotel in Hancock. Enjoy free Wi-Fi, free parking and a 24-hour fitness centre. Our guests praise the helpful staff and the property condition ...
9.2/10 Wonderful! (565 reviews)
Cleanliness
Reviewed on 9 Dec 2025

Chambery Inn
199 Main St Lee MA
Stay at this B&B in Lee. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Popular attractions Berkshire Mountain Country Store and Animagic Museum of ...
9.4/10 Exceptional! (373 reviews)
We LOVED our mini getaway at the Chambery Inn. The room was gorgeous, spacious, and very comfortable. The fireplace couldn't have been easier to operate. The jetted tubs were divine with plenty of hot water the towel warmer was a nice bonus. The room was fully stocked with glassware and a corkscrew ...
Reviewed on 3 Nov 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
