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.
Hampton Inn Albany-Wolf Road (Airport)
Price was CA $1,315, price is now CA $1,074 per person
CA $1,074
per person
Jun 28 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.8/10 Excellent! (1,010 reviews)
Staff was great. Bathrooms could use a little upkeep.
Reviewed on May 1, 2026
The Cornell Inn, Lenox & The Berkshires
Price was CA $2,976, price is now CA $2,089 per person
CA $2,089
per person
Jun 28 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9.2/10 Wonderful! (1,004 reviews)
Lovely Inn , comfy bed and suite. The breakfast was delicious…especially enjoyed the frittata, fresh baked sweet breads, and latte. Appreciated the fireplace and cognac nightcap served on on a cool April evening ,coming back from a delicious dinner in Lenox. Kool speak easy style bar, good vibes!
Reviewed on May 1, 2026
Hideaway Inn Lenox
Price was CA $2,103, price is now CA $1,612 per person
CA $1,612
per person
Jun 28 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
6/10 (1 review)
The room was comfortable and well done. There was no heat in our room with no control for the air unit. There was also a drip coming from the exhaust fan in the bathroom. We were only there one night so I didn't call for support.
Reviewed on Apr 16, 2026
The White House Inn
Price was CA $1,881, price is now CA $1,550 per person
CA $1,550
per person
Jul 14 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9.2/10 Wonderful! (309 reviews)
This property was a delight. Complementary breakfast was terrific along with the restaurant for dinner. Rooms were clean and quiet.
Reviewed on Apr 28, 2026
Vacation Village in the Berkshires
Price was CA $1,337, price is now CA $1,105 per person
CA $1,105
per person
Jun 28 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.8/10 Excellent! (2,342 reviews)
Muito bom para aproveitar em família ou a 2
Reviewed on May 3, 2026
Great Barrington Hotel Deals
Quality Inn Great Barrington
372 Main Street Great Barrington MA
Fully refundable
The price is CA $115 per night from May 27 to May 28
CA $115
CA $129 total
May 27 - May 28
includes taxes & fees
8.4/10 Very Good! (1,007 reviews)
Love it
Reviewed on May 6, 2026
Monument Mountain Motel
247 Stockbridge Rd Great Barrington MA
Fully refundableReserve now, pay when you stay
The price is CA $93 per night from May 17 to May 18
CA $93
CA $104 total
May 17 - May 18
includes taxes & fees
9/10 Wonderful! (849 reviews)
Location
Reviewed on May 4, 2026
The Little Lion
506 Stockbridge Road Great Barrington MA
Fully refundableReserve now, pay when you stay
The price is CA $150 per night from May 13 to May 14
CA $150
CA $167 total
May 13 - May 14
includes taxes & fees
8.6/10 Excellent! (559 reviews)
Second time staying. We like that dogs stay free, and that they can run outback. Nearby hiking. Easy parking. Check-in is easy. But, it’s ultimately a dingy roadside motel with a funky coat of paint, and a vintage photo on the wall. Shower had hair on floor, wall, and curtain. Soap dispensers (what ...
Reviewed on May 3, 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.
Discover the most popular places to visit in Great Barrington
Lake Mansfield Park
Explore the great outdoors at Lake Mansfield Park, a lovely green space in Great Barrington. Experience the area's theater scene and live music.
Lake Buel
Commune with nature and explore the great outdoors at Lake Buel during your travels in Great Barrington. While you're here, you can savor the top-notch restaurants.
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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.
