Great Barrington, MA

Travel Guide

Great Barrington
Great Barrington which includes city views
Great Barrington showing central business district, cafe lifestyle and outdoor eating
Great Barrington showing a church or cathedral
Great Barrington featuring a church or cathedral
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.

Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
The price is ¥13,688 per night from Sep 2 to Sep 3
¥13,688
¥15,289 total
Sep 2 - Sep 3
includes taxes & fees
Book a 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 ...
8.2/10 Very Good! (1,003 reviews)
"Good"

Reviewed on Aug 8, 2025

Quality Inn
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
The price is ¥22,309 per night from Aug 26 to Aug 27
¥22,309
¥24,920 total
Aug 26 - Aug 27
includes taxes & fees
Book a 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 ...
9.2/10 Wonderful! (724 reviews)
"Very clean. Staff was friendly and responsive."

Reviewed on Aug 6, 2025

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 out of 5
415 Stockbridge Rd, Great Barrington, MA
The price is ¥18,320 per night from Sep 1 to Sep 2
¥18,320
¥20,464 total
Sep 1 - Sep 2
includes taxes & fees
Book a 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 ...
8.8/10 Excellent! (645 reviews)
"Quiet"

Reviewed on Aug 9, 2025

Holiday Inn Express Hotel & Suites Great Barrington by IHG
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.
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

Great Barrington
Stay at this vacation home in Great Barrington. Enjoy private pools, a water park, and a garden. Popular attractions W.E.B. Du Bois Boyhood Homesite and Mahaiwe ...
10/10 Exceptional! (54 reviews)
Perfect stay!
"We loved Manor Lane! It had every amenity you could ask for. The house is fun and charming and there are thoughtful touches everywhere you look! We had fun watching movies in the living room, playing games in the lounge, cooking family meals in the spectacular kitchen and playing tennis in the sunshine. ..."

Reviewed on Apr 20, 2025

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
Exclusive Estate, Heated Yearround Outdoor Pool

Exclusive Estate, Heated Yearround Outdoor Pool

Egremont
Stay at this vacation home in Great Barrington. Enjoy private pools, a garden, and laundry facilities. Popular attractions Catamount Aerial Adventure Park and ...
9.6/10 Exceptional! (19 reviews)
2025 Family Trip
"The property was well located for seeing all in the Berkshires. We reserved 2 houses and the other property was our main location, so I only visited this property on check-in. I was told the beds may be in need of replacement. Otherwise, it worked great for us."

Reviewed on Jul 3, 2025

Exclusive Estate, Heated Yearround Outdoor Pool
Stay Lakeside This Summer!

Stay Lakeside This Summer!

Great Barrington
Stay at this vacation home in Great Barrington. Enjoy a garden, laundry facilities, and patios. Popular attractions Art et Industrie and Monument Mountain are ...
9.8/10 Exceptional! (74 reviews)
Lovely lake stay
"Beautiful lake views, comfy and cozy house! We had a wonderful time. Thank you for sharing your home with us."

Reviewed on Jun 26, 2025

Stay Lakeside This Summer!
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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