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
The Perch Hotel
The Old Catskill Game Farm Inn
Relax in Style at Historic Modern on Main With Modern Amenities & Wooded Views
Hudson Whaler

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Great Barrington Hotel Deals

Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
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

Quality Inn Great Barrington
Monument Mountain Motel

Monument Mountain Motel

2.5 out of 5
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

Monument Mountain Motel
The Little Lion

The Little Lion

3 out of 5
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

The Little Lion
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.

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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.