Great Barrington
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) of scenic 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.

Days Inn by Wyndham Great Barrington
Days Inn by Wyndham Great Barrington
2 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Free CancellationReserve now, pay when you stay
The price is $93 per night from Jun 21 to Jun 21
Situated in Great Barrington, this motel is within a 10-minute walk of Mahaiwe Performing Arts Center and Housatonic River. Lake Mansfield Park and W.E.B. Du ...
3.8/5Good! (694 reviews)
"This was pretty nice, but they need more plugs for devices."

Reviewed on Jun 1, 2021

Days Inn by Wyndham Great Barrington
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
Free Cancellation
The price is $101 per night from Jun 21 to Jun 21
Situated on a river, this hotel is 0.1 mi (0.1 km) from Housatonic River and 2.8 mi (4.6 km) from Ski Butternut. Lake Mansfield Park and Mahaiwe Performing Arts ...
4.3/5Excellent! (146 reviews)
"The hotel was super clean, with a pool that was big enough for a small group. My daughter and i went there twice and we were the only ones there."

Reviewed on Jun 7, 2021

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
Free CancellationReserve now, pay when you stay
The price is $114 per night from Jun 21 to Jun 21
This family-friendly Great Barrington hotel is located in the mountains, within 2 mi (3 km) of Housatonic River, Lake Mansfield Park, and Mahaiwe Performing ...
4.5/5Wonderful! (434 reviews)
"It was clean and had everything you need."

Reviewed on May 27, 2021

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.
Nestled Minutes From Main Street, Great Barrington
Nestled Minutes From Main Street, Great Barrington
Great Barrington, MA
This family-friendly apartment building is located in the city center, within 1 mi (2 km) of Housatonic River and Mahaiwe Performing Arts Center. Lake Mansfield ...
4.9/5Exceptional! (19 reviews)
Excellent
"Great location and very nicely kept space!"

Reviewed on Jun 11, 2021

Nestled Minutes From Main Street, Great Barrington
#2 - Nestled Minutes From Main Street, Great Barrington
#2 - Nestled Minutes From Main Street, Great Barrington
Great Barrington, MA
Situated in Great Barrington, this apartment building is within 1 mi (2 km) of Housatonic River and Mahaiwe Performing Arts Center. W.E.B. Du Bois Boyhood Homesite ...
4.9/5Exceptional! (8 reviews)
Central, clean, character
"The character and aesthetic decor in this condo are wonderful and as described in the listing and photos. I believe this is the first rental I have stayed that is primarily for rental purposes and not a lived-in space for the owner, and it was so comfortable to be in a space designed for me as a ..."

Reviewed on May 21, 2021

#2 - Nestled Minutes From Main Street, Great Barrington
Great Barrington Apartment, Short Walk to Downtown
Great Barrington Apartment, Short Walk to Downtown
Great Barrington, MA
This family-friendly Great Barrington apartment building is within a 15-minute walk of Housatonic River and Mahaiwe Performing Arts Center. Ski Butternut is ...
4.9/5Exceptional! (33 reviews)
Weekend Getaway
"We had a great trip to the Berkshires and this house was a great location from which to explore. The house was very clean and as advertised. It was close to downtown and was easy access to the different waterfalls and towns in the area. Krista and Tony were very responsive and provided good feedback ..."

Reviewed on May 25, 2021

Great Barrington Apartment, Short Walk to Downtown
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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