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 Wiltwyck
Price was CA $1,181, price is now CA $1,023 per person
CA $1,023
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Albany (ALB)
9.4/10 Exceptional! (181 reviews)
Beautiful place with historic character and charm. Nice, large fluffy towels and pillows on the bed.
Reviewed on Apr 25, 2026
The Perch Hotel
Price was CA $1,630, price is now CA $1,149 per person
CA $1,149
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Albany (ALB)
9.6/10 Exceptional! (28 reviews)
Such an amazing stay at the Perch - beautiful place with spacious rooms and a super cozy vibe. We felt right at home upon arrival and can’t wait to venture back again in the near future. Definitely recommend staying here!!
Reviewed on Feb 21, 2026
The Old Catskill Game Farm Inn
Price was CA $5,008, price is now CA $4,139 per person
CA $4,139
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Albany (ALB)
9.8/10 Exceptional! (32 reviews)
This place is a True Find. It just isn't your typical Inn experience. If you are up for a truly unique and eclectic atmosphere, gorgeously reclaimed, then dust off your Safari Hat and come to be delighted. Be sure to find time to chat with the manager Shawn and his posse of goats! We look forward to coming back with friends!
Reviewed on Apr 11, 2026
Great Barrington Hotel Deals
Quality Inn Great Barrington
372 Main Street Great Barrington MA
Fully refundable
The price is CA $108 per night from Apr 29 to Apr 30
CA $108
CA $120 total
Apr 29 - Apr 30
includes taxes & fees
8.4/10 Very Good! (1,004 reviews)
Love the place
Reviewed on Apr 27, 2026
Monument Mountain Motel
247 Stockbridge Rd Great Barrington MA
Fully refundableReserve now, pay when you stay
The price is CA $98 per night from May 5 to May 6
CA $98
CA $110 total
May 5 - May 6
includes taxes & fees
9/10 Wonderful! (845 reviews)
This is a great choice for folks traveling on a budget. Clean rooms, friendly owners, and nice retro vibe. Will be staying here again on my trips through the Berkshires.
Reviewed on Apr 26, 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 Apr 30 to May 1
CA $150
CA $167 total
Apr 30 - May 1
includes taxes & fees
8.6/10 Excellent! (556 reviews)
A nice safe and quiet place to stay. Park right in front of your door. My dog loved the large grass area. The room was large and the beds very comfortable. The heat was on when we arrived which was great . It was cold and snowy that day. I loved having the self check-in and check out. We plan on ...
Reviewed on Apr 20, 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.
