Western Massachusetts Ski Vacations

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

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Planning your Western Massachusetts ski vacation

What are some things I should consider when booking a Western Massachusetts ski trip package?

Yes, you want pristine powder and perfect runs, but take a moment to consider how close you want to be to the slopes, what extras you want from your resort, and—of course—how much après ski you intend to indulge in.

How can I find cheap Western Massachusetts ski packages?

Fly down the slopes during low or shoulder season, either side of , for a ski package to please your purse. Right now, ski trips start at just . Prices and availability are subject to change. Additional terms may apply.

Can I book a beginner ski package in Western Massachusetts?

Yes! Head for the green runs—wide, sweeping slopes—for a gentle introduction to snow life in Western Massachusetts. Book lessons so you can gear up to take on the rest of the mountain with confidence. Après awaits for all after an eventful day in the snow.

How much does a ski trip to Western Massachusetts cost?

Sensational ski trips to Western Massachusetts start from . Use the budget filter to find powder at your perfect price. As always, prices and availability are subject to change. Additional terms may apply.

When’s the best time of year to plan a ski trip to Western Massachusetts?

The best time to hit the slopes in Western Massachusetts depends on what you’re looking for. If you’re all about powder-packed pistes and brilliant blue-sky skiing conditions, aim for the middle of the season. Alternatively, if you’re willing to take a chance on start or end of season snow, you’ll bag much cheaper prices —just make sure there’s a spa or après bar to shelter in on white-out days.

Can I book Western Massachusetts ski packages with airfare?

Save money on your snow time by booking your accommodation, airfare, and car rental in a brilliant bundle. It’s both convenient and cash-flow friendly.

Can I book a Western Massachusetts ski trip with free cancellation and/or flexible dates?

Flexibility is always a bonus when you’re flying down the slopes—and it makes for an easier booking process, too. Check the payment option filter to find trips with free cancellation as well as buy now, pay later options.

Why should I book a ski package in Western Massachusetts with Expedia?

Simple search and fantastic filters make it easy to find, build, and book your dream Western Massachusetts ski vacation in just a few clicks. It’s ‘snow’ joke, it really is that easy.

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! (1,957 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

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 Aug 19, 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! (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

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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.