Great Barrington, MA

Travel Guide
Great Barrington
Enjoy fine dining and antique shopping at this Berkshires hub, along with hiking, biking and skiing in the surrounding countryside.

Visit Great Barrington, the largest town in the southwest Berkshires, for outdoor activities. With more hotels, restaurants and services than in neighboring towns and villages, it’s an ideal weekend destination and a great base for exploring the area.

While Great Barrington oozes with colonial charm, the town is not sleepy. You’ll find plenty to see and do. Get acquainted with the town center by strolling along Main Street and browsing numerous antique stores. Before shopping, consider converting your dollars into Berkshares. This local currency experiment is designed to strengthen the area’s economy visitors who use Berkshares receive discounts.

Later, select from the town’s great restaurants and funky bars. Great Barrington is home to many ex-New Yorkers and is a popular weekend destination for Manhattanites. Its diverse and sophisticated selection of restaurants appeals to this cultured clientele. Head to the Saturday farmers market for fresh, locally sourced produce.

Great Barrington has cultural attractions too. For drama, film and concerts, visit the Mahaiwe Performing Arts Center. Built in 1905, this local institution is still going strong after more than a century. Enjoy an art exhibit at the Vault Gallery and look for the namesake vault with the safe door still intact from the days when the building was used as a bank.

While staying here, explore the great outdoors in a variety of ways. Head for the nearby nature reservation of Bartholomew’s Cobble, a rocky, tree-covered knoll with 6 miles (10 kilometers) ofscenic hiking trails. Just a 10-minute drive from the town, you’ll find Monument Mountain, which offers breathtaking views over the Housatonic River Valley. In winter, hit the slopes at the popular local ski resort Ski Butternut, which is 3 miles (5 kilometers) from Great Barrington.

Reach Great Barrington in about 2.5 hours from Boston or New York. Getting to and around this rural area is easiest by car. After enjoying everything the town center offers, grab a map and head out to see the spectacular countryside.

Quality Inn
Quality Inn
2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA, 01230
The price is $118 per night from Aug 18 to Aug 19
Stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
3.9/5 Good! (813 reviews)
"Room was ready before 3:00 PM so I didn't have to wait to check in. Room was clean, spacious and well laid out. However, fridge lacked a freezer compartment which made it impossible to keep any highly perishable items I wanted to take home with me or to have ice water readily available. Also, TV ..."

Reviewed on Jul 28, 2022

Quality Inn
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
2.5 out of 5
415 Stockbridge Rd, Great Barrington, MA, 01230
Fully refundable
The price is $131 per night from Sep 6 to Sep 7
Stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
4.3/5 Excellent! (317 reviews)
"Good"

Reviewed on Aug 8, 2022

Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 out of 5
249 Stockbridge Rd, Great Barrington, MA, 01230
Fully refundableReserve now, pay when you stay
The price is $161 per night from Sep 6 to Sep 7
Stay at this family-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
4.6/5 Wonderful! (538 reviews)
"Convenient location. Good breakfast. Very clean. Professional staff."

Reviewed on Aug 9, 2022

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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.
Cozy Log Cabin adjacent to Beartown Forest, AT, and minutes to Skiing
Cozy Log Cabin adjacent to Beartown Forest, AT, and minutes to Skiing
Monterey, MA
Stay at this cabin in Great Barrington. Enjoy free WiFi, onsite parking, and a garden. Popular attractions Lake Buel and Ski Butternut are located nearby. Discover ...
5/5 Exceptional! (6 reviews)
Perfection in the Berkshires
"From the time I booked this cabin, the owner, Eric, was extremely accommodating, since I have only used VRBO once before. The payment process was flawless, and all of my pre-arrival questions were answered. Upon arrival, the cabin was just what we expected...clean, bright, well- furbished, and in ..."

Reviewed on Aug 1, 2022

Cozy Log Cabin adjacent to Beartown Forest, AT, and minutes to Skiing
Nestled minutes from Main Street, Great Barrington
Nestled minutes from Main Street, Great Barrington
Great Barrington, MA
Stay at this family-friendly apartment in Great Barrington. Enjoy WiFi, onsite parking, and a garden. Popular attractions Mahaiwe Performing Arts Center and ...
4.9/5 Exceptional! (71 reviews)
Great Barrington
"I enjoyed being in this area since I had never been. Short distance to places we wanted to visit. Great restaurants. Home was clean and comfortable. Close to town. Owner was very helpful. Nice weekend away."

Reviewed on Aug 8, 2022

Nestled minutes from Main Street, Great Barrington
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Great Barrington, MA
Stay at this vacation home in Great Barrington. Enjoy an in-room DVD player, barbecue grills, and a patio. Popular attractions Norman Rockwell Museum and Chesterwood ...
3.7/5 Good! (24 reviews)
Peaceful surroundings
"The house is spacious. Beds comfortable, sheets and towels soft. I've never been to a rental with so many amenities. Bathrooms and kitchen well stocked. We spent almost all our time on the huge deck and around the fire pit. I do think older people and small children would have difficulty with all ..."

Reviewed on Jul 9, 2022

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
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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