Western Massachusetts Ski Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Groovy Trip
  • Plan, book, travel with confidence

  • payments icon

    Better together

    Save up to NZ$616 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 Western Massachusetts Hotels

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
  • 1 hour drive from Six Flags New England
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! (1,959 reviews)
"The property was nice and had activities like a volley ball net and basketball court however no balls were provided. All together the property was very nice but had potential to be nicer. Also daytime front desk staff were not very helpful and actually cranky sounding. Not so pleasant to deal ..."

Reviewed on 20 Aug. 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
  • 1 hour drive from Six Flags New England
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 19 Aug. 2025

The Yankee, Trademark Collection by Wyndham
Berkshire Valley Inn

Berkshire Valley Inn

2.5 out of 5
2541 Hancock Rd, Williamstown, MA
  • 1 hour drive from Six Flags New England
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! (558 reviews)
"Berkshire Valley Inn was such a unique and comfortable place to stay. Best: the care taken to provide comfort (wonderful beds!). Sofa in living area had a chaise on one end so me, hub, and pup all watched TV in true 'lounge-like-you're at home' style'. They made sure I had Gluten free options included ..."

Reviewed on 21 Aug. 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.