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.
Best Western Plus Franklin Square Inn Troy/Albany
Price was CA $1,241, price is now CA $1,199 per person
CA $1,199
per person
Dec 21 - Dec 24
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Albany (ALB)
8.8/10 Excellent! (1,001 reviews)
We had a 3 night/4 day stay and our room was never cleaned/made up the entire time. I also do not appreciate that breakfast is shut down at 9 am… this does not work for many people. It should be available until AT LEAST 10 am. The parking lot is being worked on and is a bit of a mess.
Reviewed on Oct 30, 2026
The Stockade Inn
Stockade Historic District
Price was CA $1,384, price is now CA $1,338 per person
CA $1,338
per person
Dec 21 - Dec 24
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Albany (ALB)
9.4/10 Exceptional! (222 reviews)
PERFECT location should the Historic District be of interest...Recommend Solana Bagel & Coffee Shop within the premises...Arthur's Market on Ferry St., Stella's Pasta Bar and Bistro on Union St... Pleasant and responsive staff...Recommend...
Reviewed on Oct 31, 2026
Great Barrington Hotel Deals
Quality Inn Great Barrington
372 Main Street Great Barrington MA
Fully refundable
The price is CA $98 per night from Dec 2 to Dec 3
CA $98
CA $110 total
Dec 2 - Dec 3
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"I booked this for one of my bus drivers & he told me he had a good time theree in the hotel. Clean & quiet."
Reviewed on Oct 30, 2026
Prospect Berkshires
50 Prospect Lake Rd Egremont MA
The price is CA $333 per night from Nov 30 to Dec 1
CA $333
CA $419 total
Nov 30 - Dec 1
includes taxes & fees
10/10 Exceptional! (49 reviews)
"Great experience!"
Reviewed on Oct 31, 2026
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
249 Stockbridge Rd Great Barrington MA
Fully refundableReserve now, pay when you stay
The price is CA $224 per night from Nov 8 to Nov 9
CA $224
CA $251 total
Nov 8 - Nov 9
includes taxes & 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.
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.
