The Berkshires Ski Holidays 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

13 min walk from Jiminy Peak Mountain Resort

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

8.8/10 Excellent! (2,691 reviews)

"Great place great price!"

Reviewed on 1 Oct 2026

The Yankee Inn

461 Pittsfield Rd Lenox MA

25 min drive from Jiminy Peak Mountain Resort

Stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. ...

9.2/10 Wonderful! (1,002 reviews)

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

Reviewed on 1 Oct 2026

Berkshire Valley Inn

2541 Hancock Rd Williamstown MA

8 min drive from Jiminy Peak Mountain Resort

Stay at this hotel in Williamstown. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms in their reviews. ...

9.2/10 Wonderful! (581 reviews)

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

Reviewed on 1 Sept 2026

See all 1,092 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.