Photo by Photo courtesy of Berkshire Visitors Bureau
Open Photo by Photo courtesy of Berkshire Visitors Bureau
The Berkshires Ski Vacations
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Top Ski vacation packages in The Berkshires
Price found within the past 48 hours. Click for updated prices.
- Best Western Plus Berkshire Hills Inn & Suites
Oct 12 - Oct 16Best Western Plus Berkshire Hills Inn & Suites + Flight
Pittsfield4 nights2.5 star property8.6/10 - Excellent (1,002 reviews)".. "Reviewed July 20, 2026Roundtrip • Atlanta (ATL) - Albany (ALB)ATL - ALB • Nonstop ALB - ATL • 1 stop$680$596found 1 day agoper traveler - The Cornell Inn, Lenox & The Berkshires
Oct 12 - Oct 16The Cornell Inn, Lenox & The Berkshires + Flight
Lenox4 nights3.5 star property9.2/10 - Wonderful (1,003 reviews)"The entire staff was amazing and the inn was beautiful, we will definitely be back"Reviewed July 21, 2026Roundtrip • Atlanta (ATL) - Albany (ALB)ATL - ALB • Nonstop ALB - ATL • 1 stop$1,313$939found 1 day agoper traveler - Gedney Farm
Oct 12 - Oct 16Gedney Farm + Flight
Great Barrington4 nights3.5 star property9.2/10 - Wonderful (139 reviews)"Pet friendly and amazing grounds"Reviewed July 17, 2026Roundtrip • Atlanta (ATL) - Albany (ALB)ATL - ALB • Nonstop ALB - ATL • 1 stop$1,049$787found 1 day agoper traveler - Hideaway Inn Lenox
Oct 12 - Oct 16Hideaway Inn Lenox + Flight
Lenox4 nights2.0 star property7.6/10 - Good (23 reviews)"The Hideaway Inn itself was charming. The rooms were clean and beautifully decorated. We enjoyed the grounds and the lovely sitting room on the first floor. The Hideaway is very conveniently located and we appreciated being able to walk into town for food and entertainment. The only drawback to staying there was the check in process. There was no staff at all on the premises and so check in was all done digitally. Unfortunately, I couldn't open the email message I had been sent with the..."Reviewed July 21, 2026Roundtrip • Atlanta (ATL) - Albany (ALB)ATL - ALB • Nonstop ALB - ATL • 1 stop$1,070$841found 1 day agoper traveler - The Whitlock
Oct 12 - Oct 16The Whitlock + Flight
Lenox4 nights2.0 star property8.4/10 - Very Good (333 reviews)"Great location!"Reviewed July 21, 2026Roundtrip • Atlanta (ATL) - Albany (ALB)ATL - ALB • Nonstop ALB - ATL • 1 stop$1,004$797found 1 day agoper traveler
Discover the most popular places to visit in The Berkshires
Photo by Caminante
Open Photo by Caminante
Massachusetts Museum of Contemporary Art
9.4/10 (246 reviews)
This converted factory houses one of America's largest contemporary art museums. Wander through MASS MoCA's vast industrial galleries to experience thought-provoking works that transcend artistic boundaries.
Photo by Caitlin Reese
Open Photo by Caitlin Reese
Mount Greylock
9.4/10 (180 reviews)
Massachusetts' highest peak rewards hikers with panoramic views stretching 90 miles on clear days. Explore the Appalachian Trail segment or stay overnight at the historic Bascom Lodge for a summit sunrise experience.
Top Ski The Berkshires Hotels
9.2 out of 10, Wonderful, (1,009 reviews)
9.2/10
Wonderful
(1,009 reviews)
"The room was neat and had access to outside to enjoy sitting. The fridge in the room was a convenient size for cold and frozen foods. The staff was responsive to issues, even when I told them they could wait to fix it until after we left (it was fixed quickly. The breakfast was excellent and offered a nice variety. Would happily stay here again."
$195 nightly
The price is $218
$218 total
Jul 22 - Jul 23
Total with taxes and fees
9.0 out of 10, Wonderful, (1,017 reviews)
9.0/10
Wonderful
(1,017 reviews)
$155 nightly
The price is $173
$173 total
Aug 20 - Aug 21
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHG2.5 star property
10.5 mi from The Berkshires
8.8 out of 10, Excellent, (793 reviews)
8.8/10
Excellent
(793 reviews)
"The phone, shower head and amenities were lacking.
Except for the gentleman who check me in (Steve) I really didn't see anyone else. He seemed to be working there 24 hours.
The lampshades on the bed lamps were broken and gerry rigged to stay on . The phone was broken and the shower head dribbled until I fixed it myself.
For the price I paid, over a thousand dollars for 2 nights...I expected better.."
$139 nightly
The price is $155
$155 total
Jul 26 - Jul 27
Total with taxes and fees
Quality Inn Great Barrington
Quality Inn Great Barrington2.5 star property
11.2 mi from The Berkshires
8.6 out of 10, Excellent, (1,005 reviews)
8.6/10
Excellent
(1,005 reviews)
"The location of this hotel is excellent. However, there was blood on the bathroom floor, stains on the sheets, and the fridge reeked of beer. When we asked the maintenance crew to give us five minutes to get out of the room, the cart was outside our door so we assumed that they would return and change the towels. They did not. The gentleman who checked me in was lovely; however, there was no one in the office when we checked out."
$118 nightly
The price is $132
$132 total
Aug 11 - Aug 12
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires3.5 star property
15.3 mi from The Berkshires
9.2 out of 10, Wonderful, (1,003 reviews)
9.2/10
Wonderful
(1,003 reviews)
"The entire staff was amazing and the inn was beautiful, we will definitely be back"
$172 nightly
The price is $192
$192 total
Jul 22 - Jul 23
Total with taxes and fees
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG3.5 star property
9.7 mi from The Berkshires
9.2 out of 10, Wonderful, (941 reviews)
9.2/10
Wonderful
(941 reviews)
"Rooms had not been updated since the seventies."
$177 nightly
The price is $198
$198 total
Jul 27 - Jul 28
Total with taxes and fees
8.8 out of 10, Excellent, (1,006 reviews)
8.8/10
Excellent
(1,006 reviews)
$223 nightly
The price is $249
$249 total
Jul 27 - Jul 28
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel3.0 star property
12.1 mi from The Berkshires
9.2 out of 10, Wonderful, (1,007 reviews)
9.2/10
Wonderful
(1,007 reviews)
$167 nightly
The price is $187
$187 total
Jul 22 - Jul 23
Total with taxes and fees
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.
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.
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 $596. 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 $596. 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.