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.
The Palmer House Resort, an Ascend Collection Hotel
Price was CA $1,095, price is now CA $1,043 per person
CA $1,043
per person
Jun 28 - Jul 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
8.4/10 Very Good! (935 reviews)
Always enjoy our stay there
Reviewed on May 23, 2026
The Equinox Golf Resort & Spa
Manchester Village Historic District
Price was CA $1,228, price is now CA $1,084 per person
CA $1,084
per person
Jun 28 - Jul 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
7.4/10 Good! (621 reviews)
It was a beautiful setting! Service was slow. Our room had a slight smell to it and the pull out couch was dirty. We were very hopeful and are very understanding. Sharing this input to help hotel improve their services.
Reviewed on May 26, 2026
The White House Inn
Price was CA $1,271, price is now CA $1,164 per person
CA $1,164
per person
Jun 28 - Jul 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
9.2/10 Wonderful! (312 reviews)
Gorgeous property, wonderful staff. We’ll be coming back here again!!
Reviewed on May 22, 2026
The Manchester View
Price was CA $1,148, price is now CA $1,101 per person
CA $1,101
per person
Jun 28 - Jul 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
9.4/10 Exceptional! (821 reviews)
Beautiful property, clean room, friendly staff. Will definitely be staying here again!
Reviewed on Mar 18, 2026
Kimpton Taconic Hotel by IHG
Manchester Village Historic District
Price was CA $1,347, price is now CA $1,298 per person
CA $1,298
per person
Jun 28 - Jul 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
9.4/10 Exceptional! (841 reviews)
Great spot in Manchester! Perfect for families or couples!
Reviewed on May 22, 2026
Great Barrington Hotel Deals
Quality Inn Great Barrington
372 Main Street Great Barrington MA
Fully refundable
The price is CA $117 per night from May 31 to Jun 1
CA $117
CA $130 total
May 31 - Jun 1
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
"Terrific generous breakfadt menu, cozy eating lounge. The room was in tip top shape and the hotel is superbly located right on Main Street and in walking proximity of shops, stores restaurants and cafes. Ideal place to stay abd reasonably priced room rates."
Reviewed on May 26, 2026
The Little Lion
506 Stockbridge Road Great Barrington MA
Fully refundableReserve now, pay when you stay
The price is CA $131 per night from Jun 11 to Jun 12
CA $131
CA $146 total
Jun 11 - Jun 12
includes taxes & fees
8.6/10 Excellent! (562 reviews)
"Great"
Reviewed on May 25, 2026
Monument Mountain Motel
247 Stockbridge Rd Great Barrington MA
Fully refundableReserve now, pay when you stay
The price is CA $106 per night from Jun 2 to Jun 3
CA $106
CA $119 total
Jun 2 - Jun 3
includes taxes & fees
9/10 Wonderful! (857 reviews)
"Very nice motel with clean rooms and bathrooms. AC and heat both work well and the heater in the bathroom makes cold mornings easy to deal with. Easy access to your room and everything the Berkshires have to offer."
Reviewed on May 25, 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.
