Western Massachusetts Ski Vacations
Book a Ski Hotel + Flight or Car together to unlock savings
Photo by Groovy Trip
- Plan, book, travel with confidence
Better together
Save up to ₩234,741 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 Western Massachusetts 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! (1,957 reviews)
"A rare, affordable place in the Berkshires! The scenery is stunning, and we loved the pools (both indoor and out) and fire pit. The staff was friendly, and our room was spacious but dated: the blinds were broken, the doors stuck, the walls were paper thin and our king-size mattress had clearly seen ..."
Reviewed on Aug 18, 2025
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! (1,010 reviews)
"My stay was very good"
Reviewed on Aug 19, 2025
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! (557 reviews)
Family fun
"I stayed with my daughter and 2 grandchildren. The room was clean and adorable. They have several otems in the room that you can purchase if needed. We did have 2 of the waters. The pool was very clean and had several floats you can use. The breakfast was also good. Choices of fruit, yogurt, scones, ..."
Reviewed on Aug 19, 2025
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.