The Berkshires Ski Vacations
Book a Ski Hotel + Flight or Car together to unlock savings
Photo by Photo courtesy of Berkshire Visitors Bureau
Better together
Save up to NT$5,067 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Top Ski The Berkshires Hotels
Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,860 reviews)
"Activities look good during week but we miss them on our weekend stay"
Reviewed on 2025/7/8
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd, Lenox, MA
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 ...
9/10 Wonderful! (1,011 reviews)
Great location for Tanglewood
"Friendly staff, clean rooms and a very nice breakfast buffet. Staff went out f their way to help locate and ship two items that I had left behind."
Reviewed on 2025/7/10
Berkshire Valley Inn
2541 Hancock Rd, Williamstown, MA
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. ...
9/10 Wonderful! (549 reviews)
"Beautiful property, wonderful staff, great breakfast."
Reviewed on 2025/6/23
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.