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 $1,342, price is now CA $1,250 per person
CA $1,250
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Albany (ALB)
8.8/10 Excellent! (1,004 reviews)
We had to leave before breakfast and our 'to go' bag was not ready as the evening staff said it would be. The shuttle driver was ready, so that is what really mattered.
Reviewed on Jun 30, 2026
The White House Inn
Price was CA $1,469, price is now CA $1,342 per person
CA $1,342
per person
Sep 18 - Sep 21
found 15 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Albany (ALB)
9.2/10 Wonderful! (328 reviews)
Beautiful historical inn with so much charm and friendly staff.
Reviewed on Jun 30, 2026
Brook Bound Inn
Price was CA $1,571, price is now CA $1,449 per person
CA $1,449
per person
Sep 18 - Sep 21
found 15 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Albany (ALB)
9.2/10 Wonderful! (16 reviews)
The cabin and grounds are well-maintained. The pool was crystal clear and the slide was a nice addition. Gorgeous views!
Reviewed on Jun 28, 2026
La Quinta Inn & Suites by Wyndham Clifton Park/Saratoga Area
Price was CA $1,511, price is now CA $1,409 per person
CA $1,409
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Albany (ALB)
8.6/10 Excellent! (1,136 reviews)
Propre et déjeuner correct.
Reviewed on Jul 1, 2026
Great Barrington Hotel Deals
Quality Inn Great Barrington
372 Main Street Great Barrington MA
Fully refundable
The price is CA $168 per night from Jul 23 to Jul 24
CA $168
CA $187 total
Jul 23 - Jul 24
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"Room was spacious and clean with a comfortable bed. Easy parking, nice quiet location. Easy walk to town."
Reviewed on Jul 1, 2026
Holiday Inn Express Hotel & Suites Great Barrington by IHG
415 Stockbridge Rd Great Barrington MA
Fully refundable
The price is CA $224 per night from Jul 27 to Jul 28
CA $224
CA $251 total
Jul 27 - Jul 28
includes taxes & fees
8.8/10 Excellent! (782 reviews)
"Great place to stay and it is convenient to local theaters and not too far from Tanglewood."
Reviewed on Jun 22, 2026
The Little Lion
506 Stockbridge Road Great Barrington MA
The price is CA $170 per night from Jul 7 to Jul 8
CA $170
CA $190 total
Jul 7 - Jul 8
includes taxes & fees
8.6/10 Excellent! (572 reviews)
"This has been a long time stop for us. It has always been a perfect location. The hotel is right at the base of Monument Mountain and it is truly breathtaking to see it out your window."
Reviewed on Jun 28, 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.
