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.

Monument Mountain Motel
Monument Mountain Motel
2.5 out of 5
247 Stockbridge Rd, Great Barrington, MA
The price is CA $88 per night from Jan 24 to Jan 25
Situated in Great Barrington, this motel is 1.6 mi (2.6 km) from Housatonic River and 2.4 mi (3.9 km) from Ski Butternut. Lake Mansfield Park and Mahaiwe Performing ...
4.4/5 Excellent! (324 reviews)
"The best accommodation you can ask for with this price; clean, quiet, well maintained with everything functioning."

Reviewed on Jan. 11, 2022

Monument Mountain Motel
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
The price is CA $121 per night from Jan 31 to Feb 1
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 ...
4.2/5 Excellent! (243 reviews)
"Common spaces were clean and open. Felt safe. Appreciated the complimentary breakfast."

Reviewed on Jan. 17, 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
The price is CA $159 per night from Jan 24 to Jan 25
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 ...
4.6/5 Wonderful! (500 reviews)
"We enjoyed the hot tub and pool tremendously. The shower was nice and hot. Also included very nice breakfast options. Staff recommended great restaurants in the area."

Reviewed on Jan. 15, 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.
LOFT ON MAIN ST
LOFT ON MAIN ST
Great Barrington, MA
The price is CA $438 per night from Jan 23 to Jan 24
Located in the heart of Great Barrington, this apartment building is within a 5-minute walk of Mahaiwe Performing Arts Center and Housatonic River. Lake Mansfield ...
5/5 Exceptional! (2 reviews)
Great location and comfortable
"My husband and I stayed here along with my cousin, and this was perfect for three people. We liked the style and the space, and being on Main Street was great."

Reviewed on Oct. 4, 2021

LOFT ON MAIN ST
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 ...
4.9/5 Exceptional! (50 reviews)
Comfortable Stay
"Candice was so helpful and kind during the check in process. Her home is immaculate and even better then described online. We will be coming back in the future. Thank you Candice for opening your home!"

Reviewed on Jan. 18, 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
Situated on the waterfront, this vacation home is 2.5 mi (4 km) from Housatonic River and within 6 mi (10 km) of Norman Rockwell Museum and Lake Mansfield Park. ...
3.5/5 Good! (21 reviews)
Perfect getaway for the family
"This getaway was exactly what we were looking for in a Berkshires vacation. Spent the weekend at the cabin with our 5 month old and friends. The Cabin is perfect for relaxing and enjoying nature. It also has everything you need for cooking, cleaning, sleeping, etc. Took a nice trip around the pond ..."

Reviewed on Apr. 16, 2021

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.

Cities near Great Barrington