The Berkshires Ski Holidays

Book a Ski Hotel + Flight or Car together to unlock savings

Photo by Photo courtesy of Berkshire Visitors Bureau
  • Plan, book, travel with confidence

  • payments icon
    Better together
    Save up to ₹43,962 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Top Ski The Berkshires Hotels

Vacation Village in the Berkshires
Vacation Village in the Berkshires
3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
  • 35 min drive from Tanglewood Music Center
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness centre and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,844 reviews)
"amazing for the price and overall SOOO clean"

Reviewed on 28 Jun 2025

Vacation Village in the Berkshires
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 out of 5
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. ...
9/10 Wonderful! (1,006 reviews)
"All was fine!"

Reviewed on 30 Jun 2025

The Yankee, Trademark Collection by Wyndham
Berkshire Valley Inn
Berkshire Valley Inn
2.5 out of 5
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. ...
9/10 Wonderful! (549 reviews)
"Beautiful property, wonderful staff, great breakfast."

Reviewed on 23 Jun 2025

Berkshire Valley Inn
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.