Massachusetts Ski Vacations

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

Top Ski vacation packages in Massachusetts

Price found within the past 48 hours. Click for updated prices.
Doubletree by Hilton Hotel Leominster
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4 Night Ski vacations in Massachusetts

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Residence Inn Boston Dedham
Comfort Inn Randolph - Boston
Homewood Suites by Hilton Boston/Canton, MA
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Planning your Massachusetts ski vacation

What are some things I should consider when booking a 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 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 $532. Prices and availability are subject to change. Additional terms may apply.

Can I book a beginner ski package in Massachusetts?

Yes! Head for the green runs—wide, sweeping slopes—for a gentle introduction to snow life in 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 Massachusetts cost?

Sensational ski trips to Massachusetts start from $532. 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 Massachusetts?

The best time to hit the slopes in 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 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 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 Massachusetts with Expedia?

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

Top Ski Massachusetts Hotels

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
  • 8 min walk from Fenway Park
$112 nightly
The price is $125 total per night from Oct 30 to Oct 31
$125 total
Oct 30 - Oct 31
Total with taxes and fees
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! (2,076 reviews)
"Room was clean"

Reviewed on Oct 17, 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
  • 13 min drive from Fenway Park
$134 nightly
The price is $150 total per night from Nov 2 to Nov 3
$150 total
Nov 2 - Nov 3
Total with taxes and fees
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 stay-- would stay here again-- safe, nice welcome from Cameron at front desk, room was clean and cozy. Bed was very comfortable. Didn't have breakfast. I usually stay in Pittsfield at a hotel that has given me a discount since March when my mother was put into a nursing home. I normally try ..."

Reviewed on Oct 16, 2025

The Yankee, Trademark Collection by Wyndham
Berkshire Valley Inn

Berkshire Valley Inn

2.5 out of 5
2541 Hancock Rd, Williamstown, MA
  • 14 min drive from Fenway Park
$184 nightly
The price is $206 total per night from Nov 6 to Nov 7
$206 total
Nov 6 - Nov 7
Total with taxes and fees
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! (563 reviews)
"We had a short but pleasant stay."

Reviewed on Sep 30, 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.