The Berkshires Mountain Holidays 2026

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

34 min drive from Tanglewood Music Center

Stay at this hotel in Hancock. Enjoy free parking, 2 hot tubs and breakfast (surcharge). Our guests praise the property condition in their reviews. Popular attractions ...

8.2/10 Very good! (1,004 reviews)

"Jiminy Peak is located in an absolutely beatiful location in the Berkshires. And it has fun family-friendly summertime activities. But it could use some sprucing up. The pool liner is a little wrinkly and the hot tub is quite stained near the water line. In addition, our room had a nice 2-foot gouge ..."

Reviewed on 6 Aug 2026

Chambery Inn

199 Main St Lee MA

8 min drive from Tanglewood Music Center

Stay at this B&B in Lee. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Popular attractions Tanglewood Music Center and Berkshire Mountain Country ...

Eastgate Inn B&B

207 West Street Lenox MA

2 min walk from Tanglewood Music Center

Stay at this business-friendly B&B in Lenox. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Tanglewood Music Center and Frelinghuysen ...

9.2/10 Wonderful! (69 reviews)

"Dahlia is great. Excellent accommodation. We walked to Tanglewood"

Reviewed on 4 Aug 2025

See all 1,077 properties in The Berkshires

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.