The Berkshires Ski Vacations

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Photo by Photo courtesy of Berkshire Visitors Bureau
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4 Night Ski vacations in The Berkshires

Price found within the past 48 hours. Click for updated prices.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

$472
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
President Donald J. Trump Intl. Airport (DJT) to Albany (ALB)
8.8/10 Excellent! (2,598 reviews)
There was mold in the outdoor pool. There wasn’t an elevator.

Reviewed on Sep 16, 2026

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

$758
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
President Donald J. Trump Intl. Airport (DJT) to Albany (ALB)
9.2/10 Wonderful! (1,000 reviews)
Quality Inn Great Barrington

Quality Inn Great Barrington

$553
per person
Oct 19 - Oct 23
found 1 day ago
Roundtrip flight included
Nassau (NAS) to Albany (ALB)
8.6/10 Excellent! (1,000 reviews)
Beds were comfortable but the pillows not so great but clean and quiet.

Reviewed on Sep 15, 2026

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Planning your The Berkshires ski vacation

What are some things I should consider when booking a The Berkshires 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 The Berkshires ski packages?

Right now, ski trips start at just $472. Prices and availability are subject to change. Additional terms may apply.

Can I book a beginner ski package in The Berkshires?

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

Sensational ski trips to The Berkshires start from $472. 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 The Berkshires?

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

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

Top Ski The Berkshires Hotels

Vacation Village in the Berkshires

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA
  • 35 min drive from Tanglewood Music Center
Book a stay at this family-friendly aparthotel in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful ...
8.8/10 Excellent! (2,647 reviews)
"There was mold in the outdoor pool. There wasn’t an elevator."

Reviewed on Sep 16, 2026

Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

461 Pittsfield Rd Lenox MA
  • 8 min drive from Tanglewood Music Center
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 ...
The Yankee Inn
Berkshire Valley Inn

Berkshire Valley Inn

2541 Hancock Rd Williamstown MA
  • 42 min drive from Tanglewood Music Center
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. ...
9.2/10 Wonderful! (581 reviews)
"Older motel, clean, friendly would recommend to others."

Reviewed on Sep 1, 2026

Berkshire Valley Inn
See all 1,095 properties in The Berkshires
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.