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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Save up to £335 when you book a flight and hotel together*
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Packages with flights are ATOL protected
Top Mountain The Berkshires Hotels
Jiminy Peak Mountain Resort
37 Corey Rd, Hancock, MA
Stay at this 3-star ski condo in Hancock. Enjoy free parking, 2 restaurants and 2 hot tubs. Our guests praise the property condition in their reviews. Popular ...
8.2/10 Very Good! (964 reviews)
Beautiful Berkshire relaxation!
"From the pleasant staff to the comfy cozy, clean atmosphere of the room, this resort is a definite “go to” experience while vacationing in the Berkshires. The resort attractions are a family fun filled adventures that are great to experience. Our favorite was the ski lift to the top of the mountain ..."
Reviewed on 19 Aug 2025
Club Wyndham Bentley Brook
1 Corey Road, Hancock, MA
Stay at this 3-star 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! (534 reviews)
"Perfect"
Reviewed on 18 Aug 2025
Chambery Inn
199 Main St, Lee, MA
Stay at this 3-star B&B in Lee. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Popular attractions Tanglewood Music Center and Berkshire Mountain ...
9.4/10 Exceptional! (368 reviews)
"Beautiful stay. We booked last minute and it was amazing! We were able to book the room with jacuzzi and a fireplace—which made the whole stay so romantic. Will recommend and am planning to visit regularly. Hoping to return in the fall but definitely next spring. This family works hard and takes ..."
Reviewed on 13 Jun 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.