The Berkshires Ski Vacations 2026

Photo by Photo courtesy of Berkshire Visitors Bureau

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Top Ski The Berkshires Hotels

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

35 min drive from Tanglewood Music Center

Book a stay at this family-friendly aparthotel in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful ...

8.8/10 Excellent! (2,691 reviews)

"Great place great price!"

Reviewed on 2026/10/1

The Yankee Inn

461 Pittsfield Rd Lenox MA

8 min drive from Tanglewood Music Center

Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...

9.2/10 Wonderful! (1,002 reviews)

"Place is old a failing. Stay somewhere else."

Reviewed on 2026/10/1

Berkshire Valley Inn

2541 Hancock Rd Williamstown MA

42 min drive from Tanglewood Music Center

Stay at this hotel in Williamstown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...

9.2/10 Wonderful! (581 reviews)

"Older motel, clean, friendly would recommend to others."

Reviewed on 2026/9/1

See all 1,096 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.