Great Barrington Vacation Packages
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Your Great Barrington Vacation
Say goodbye to the worries of planning and hello to a Great Barrington vacation package. With the finer details organized before you take off, you can focus on discovering the best of this city, starting with Canann Village Historic District, which is good for dining, culture and shopping. Fill your spare time with visits to Ski Butternut, Housatonic River Walk and Lake Buel, some of the things you simply have to see during a trip to Great Barrington. Expedia is here to help you escape the everyday. Tailor your vacation to Great Barrington to suit your travel style, whatever that may be!
Top Great Barrington Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Vacation Village in the Berkshires
Price was CA $665, price is now CA $559 per person
CA $559
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
8.8/10 Excellent! (2,388 reviews)
The convenience of being able to share and enjoy the units A&B with my family. Both units were spacious and comfortable.
Reviewed on Jun 8, 2026
Berkshire Mountain Lodge
Price was CA $892, price is now CA $728 per person
CA $728
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
9/10 Wonderful! (960 reviews)
It's a beautiful resort. The room was literally like a home away from home. Very cozy, very clean. Has a full kitchen with a dishwasher
Reviewed on Jun 11, 2026
The Yankee Inn
Price was CA $942, price is now CA $807 per person
CA $807
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
9.2/10 Wonderful! (1,002 reviews)
The room was large, clean and comfortable. The location was near shopping and dining. The check in was quick and pleasant.
Reviewed on Jun 11, 2026
Hampton Inn Albany-Wolf Road (Airport)
Price was CA $1,248, price is now CA $1,151 per person
CA $1,151
per person
Jul 31 - Aug 2
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.8/10 Excellent! (1,007 reviews)
Quick easy. Nice staff. In a quiet section of wolf road. Actually got to sleep
Reviewed on Jun 11, 2026
Park Manor Hotel
Price was CA $1,285, price is now CA $1,197 per person
CA $1,197
per person
Jul 31 - Aug 2
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8/10 Very Good! (1,284 reviews)
Convenient location to Saratoga Springs. Hotel was relatively clean. Toilet handle needs attention as it was sticking. We left behind a nook and contacted the hotel twice with no response. Our Visa payment will be withheld until this property returns the nook to us.
Reviewed on Jun 11, 2026
Great Barrington Hotel Deals
Quality Inn Great Barrington
372 Main Street Great Barrington MA
Fully refundable
The price is CA $131 per night from Jun 15 to Jun 16
CA $131
CA $147 total
Jun 15 - Jun 16
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"Excellent location, great low price, VERY Comfortable bed- throwback era motel. Why pay more when it’s all here!"
Reviewed on Jun 7, 2026
The Little Lion
506 Stockbridge Road Great Barrington MA
Fully refundableReserve now, pay when you stay
The price is CA $123 per night from Jun 14 to Jun 15
CA $123
CA $137 total
Jun 14 - Jun 15
includes taxes & fees
8.6/10 Excellent! (564 reviews)
"Parking is"
Reviewed on Jun 5, 2026
Monument Mountain Motel
247 Stockbridge Rd Great Barrington MA
Fully refundableReserve now, pay when you stay
The price is CA $107 per night from Jun 21 to Jun 22
CA $107
CA $120 total
Jun 21 - Jun 22
includes taxes & fees
9/10 Wonderful! (867 reviews)
"Room was clean and cozy, bed comfy, pillows comfy, bathroom nice and clean, plenty of towels, AC worked, and plenty of parking for two cars since we usually travel with 2 vehicles."
Reviewed on Jun 10, 2026
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.
Stay near popular Great Barrington attractions
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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.
