Great Barrington Travel Guide

Tourist Guide

Great Barrington
Great Barrington which includes central business district
Great Barrington which includes central business district, café lifestyle and outdoor eating
Great Barrington featuring a church or cathedral
Great Barrington showing 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 centre 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 Centre. 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 kilometres) 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 kilometres) 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 centre 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 NZ$175 per night from 7 Sept to 8 Sept
NZ$175
7 Sept - 8 Sept
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! (1,005 reviews)
Great stay
"The room was clean. The carpets need to be replaced. Water pressure not great. Breakfast was good but a little crowded. The staff was super friendly and helpful. Great location for the price."

Reviewed on 15 Aug. 2025

Quality Inn
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 NZ$234 per night from 1 Sept to 2 Sept
NZ$234
1 Sept - 2 Sept
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! (649 reviews)
"Very Good; Clean, Quiet Motel, Area has many dining options."

Reviewed on 14 Aug. 2025

Holiday Inn Express Hotel & Suites Great Barrington by IHG
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 NZ$315 per night from 25 Aug to 26 Aug
NZ$315
25 Aug - 26 Aug
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! (725 reviews)
"Well maintained, can use some update. As soon as I walked in the room, I smelled the carpet. The water pressure was so low. I spent twice more time in the shower. The staff"

Reviewed on 13 Aug. 2025

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.
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Great Barrington
Stay at this vacation home in Great Barrington. Enjoy laundry facilities, patios, and cable/satellite TV service. Popular attractions Art et Industrie and Monument ...
7.2/10 Good! (45 reviews)
Christmas 2024
"The property was great overall. I was not impressed with finding cobwebs around furniture, or with the hair in the shower and the toothpaste on the sink, mirror mirrorandbehind behind"

Reviewed on 4 Jan. 2025

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
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 20 Apr. 2025

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