The Berkshires Mountain Vacations
Book a Mountain 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 ₩234,741 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 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 our reviews. Popular ...
8.2/10 Very Good! (962 reviews)
Good base to do things in the Berkshires
"We didn't spend much time there, but it was nice, comfortable, clean and quiet. It was close to the things we had planned to do."
Reviewed on Aug 11, 2025
Club Wyndham Bentley Brook
1 Corey Road, Hancock, MA
Stay at this 3-star ski hotel in Hancock. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the property condition ...
9.2/10 Wonderful! (534 reviews)
"Perfect"
Reviewed on Aug 18, 2025
Chambery Inn
199 Main St, Lee, MA
Stay at this 3-star B&B in Lee. Enjoy free WiFi, 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 Jun 13, 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.