Great Barrington Ski Vacations
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Top Ski vacation packages in Great Barrington
Price found within the past 48 hours. Click for updated prices.
- Quality Inn Great Barrington
Oct 9 - Oct 13Quality Inn Great Barrington + Flight
Great Barrington4 nights2.5 star property8.6/10 - Excellent (1,005 reviews)"Great experience. Friendly staff. Easy walk to town."Reviewed July 18, 2026Roundtrip • Atlanta (ATL) - Albany (ALB)ATL - BOS • Nonstop BOS - ATL • Nonstop$599$539found 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 20 hours agoper traveler - The Little Lion
Oct 9 - Oct 13The Little Lion + Flight
Great Barrington4 nights3.0 star property8.6/10 - Excellent (588 reviews)"Always love to stay here! Thanks"Reviewed July 20, 2026Roundtrip • Atlanta (ATL) - Albany (ALB)ATL - BOS • Nonstop BOS - ATL • Nonstop$701$628found 1 day agoper traveler - East Rock Inn
Oct 12 - Oct 16East Rock Inn + Flight
Great Barrington4 nights2.0 star property9.6/10 - Exceptional (51 reviews)"Comfy beds, clean cute and modern, I love everything about this little place. Easy check in even though it’s basically virtual they communicated clearly and quickly about my room and door code. Only thing was there was a container of someone else’s snack leftover in my mini fridge when I arrived I just threw it out. I love the real coffee mugs in the room that’s a nice touch."Reviewed July 19, 2026Roundtrip • Atlanta (ATL) - Albany (ALB)ATL - ALB • Nonstop ALB - ATL • 1 stop$887$821found 20 hours agoper traveler - The Berkshire Mountain Inn
Oct 12 - Oct 16The Berkshire Mountain Inn + Flight
Great Barrington4 nights3.0 star property9.0/10 - Wonderful (15 reviews)"The Inn was not what we were expecting but we were pleasantly surprised. The room was clean, well maintained, comfortable and had all the amenities we needed. The staff was friendly and helpful. The location was convenient to Great Barrington. Breakfast was different from other hotels but was excellent"Reviewed July 19, 2026Roundtrip • Atlanta (ATL) - Albany (ALB)ATL - ALB • Nonstop ALB - ATL • 1 stop$1,050$1,017found 20 hours agoper traveler
Discover the most popular places to visit in Great Barrington
Top Ski Great Barrington Hotels
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHG2.5 star property
1.5 mi from Great Barrington
8.8 out of 10, Excellent, (792 reviews)
8.8/10
Excellent
(792 reviews)
$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
0.3 mi from Great Barrington
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
9.0 out of 10, Wonderful, (885 reviews)
9.0/10
Wonderful
(885 reviews)
"Well situated in the Berkshires and kind staff."
$124 nightly
The price is $138
$138 total
Jul 23 - Jul 24
Total with taxes and fees
Travelodge by Wyndham Great Barrington Berkshires
Travelodge by Wyndham Great Barrington Berkshires2.0 star property
2.6 mi from Great Barrington
7.6 out of 10, Good, (594 reviews)
7.6/10
Good
(594 reviews)
"Nice room with great TV services and WiFi and even a pool"
$99 nightly
The price is $111
$111 total
Jul 26 - Jul 27
Total with taxes and fees
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires3.0 star property
1.1 mi from Great Barrington
9.4 out of 10, Exceptional, (795 reviews)
9.4/10
Exceptional
(795 reviews)
$195 nightly
The price is $217
$217 total
Aug 10 - Aug 11
Total with taxes and fees
8.6 out of 10, Excellent, (588 reviews)
8.6/10
Excellent
(588 reviews)
"This place was a gem. It’s small and surrounded by nature but close to restaurants, shopping, wildlife viewing areas, and historical sites. I loved that pets are free. The grounds were nice with a picnic bench and a large fire pit. If I’m in the area again, I would definitely stay here."
$126 nightly
The price is $141
$141 total
Aug 19 - Aug 20
Total with taxes and fees
9.6 out of 10, Exceptional, (51 reviews)
9.6/10
Exceptional
(51 reviews)
"Comfy beds, clean cute and modern, I love everything about this little place. Easy check in even though it’s basically virtual they communicated clearly and quickly about my room and door code. Only thing was there was a container of someone else’s snack leftover in my mini fridge when I arrived I just threw it out. I love the real coffee mugs in the room that’s a nice touch."
$152 nightly
The price is $170
$170 total
Aug 19 - Aug 20
Total with taxes and fees
9.0 out of 10, Wonderful, (15 reviews)
9.0/10
Wonderful
(15 reviews)
"The Inn was not what we were expecting but we were pleasantly surprised. The room was clean, well maintained, comfortable and had all the amenities we needed. The staff was friendly and helpful. The location was convenient to Great Barrington. Breakfast was different from other hotels but was excellent"
$288 nightly
The price is $321
$321 total
Jul 26 - Jul 27
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 Great Barrington ski vacation
What are some things I should consider when booking a Great Barrington 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 Great Barrington ski packages?
Right now, ski trips start at just $539. Prices and availability are subject to change. Additional terms may apply.
Can I book a beginner ski package in Great Barrington?
Yes! Head for the green runs—wide, sweeping slopes—for a gentle introduction to snow life in Great Barrington. 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 Great Barrington cost?
Sensational ski trips to Great Barrington start from $539. 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 Great Barrington?
The best time to hit the slopes in Great Barrington 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 Great Barrington 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 Great Barrington 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 Great Barrington with Expedia?
Simple search and fantastic filters make it easy to find, build, and book your dream Great Barrington ski vacation in just a few clicks. It’s ‘snow’ joke, it really is that easy.