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

35 min drive from Tanglewood Music Center

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! (2,520 reviews)

"Beautiful location and pricey, but less expensive than most places in the area. It is spacious with a kitchen that we did not use, the rooms are very dated. You can hear through the walls very well. Didn’t use pool because it was so crowded."

Reviewed on 11 Aug 2026

The Yankee Inn

461 Pittsfield Rd Lenox MA

8 min drive from Tanglewood Music Center

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! (1,023 reviews)

"The room was clean. Linens in good shape. Good access to lots of activities nearby. Breakfast can be crowded. Go early."

Reviewed on 11 Aug 2026

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 Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms in their reviews. ...

9.2/10 Wonderful! (577 reviews)

"We LOVED our stay! Pamela has done a beautiful job paying attention to the details. We will definitely be back. Highly recommend!"

Reviewed on 10 Aug 2026

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.