Find Hotels with Bars in Great Barrington, MA

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Check availability on Great Barrington Hotels with Bars

Our top choices for Great Barrington hotels with a bar

Front of property

Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.2 out of 10, Wonderful, (137 reviews)
"Had a great stay. Beautiful location."
United States
Joan
The price is AED 657
AED 721 total
includes taxes & fees
16 Jun - 17 Jun
Gedney Farm
Exterior

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.8 out of 10, Exceptional, (29 reviews)
"Great stay!"
United States
Conor
The price is AED 1,207
AED 1,471 total
includes taxes & fees
22 Jun - 23 Jun
Prospect Berkshires
Breakfast, lunch, dinner and brunch served

The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (91 reviews)
"Beautiful Inn and outstanding chef"
United States
Catherine
The price is AED 1,212
AED 1,463 total
includes taxes & fees
16 Jun - 17 Jun
The Old Inn On The Green
Superior Room, 1 King Bed, Jetted Tub | Jetted tub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,013 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Canada
Mark
The price is AED 408
AED 456 total
includes taxes & fees
16 Jun - 17 Jun
The Yankee Inn
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (988 reviews)
"Great lobby and dining room atmosphere!"
United States
Carin
The price is AED 521
AED 582 total
includes taxes & fees
17 Jun - 18 Jun
Berkshires Untold
Exterior

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,009 reviews)
"Clean room and breakfast"
United States
Raphael
The price is AED 559
AED 788 total
includes taxes & fees
22 Jun - 23 Jun
The Red Lion Inn
Restaurant

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.6 out of 10, Exceptional, (81 reviews)
"Excellent lodge, recommend."
United States
Jason
The price is AED 559
AED 626 total
includes taxes & fees
21 Jun - 22 Jun
Little Cat Lodge
Exterior

the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (226 reviews)
"It’s a wonderful place to rest for a while. it has all you need, everything it’s in good conditions also it’s near of many activities like hiking."
United States
Daniel
The price is AED 624
AED 699 total
includes taxes & fees
21 Jun - 22 Jun
the Alander
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (1,009 reviews)
"Quiet room. Comfortable bed linens"
United States
Margo
The price is AED 444
AED 496 total
includes taxes & fees
22 Jun - 23 Jun
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Deep-tissue massages, Swedish massages, facials, 5 treatment rooms

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath
2.0 star property
Hudson
8.6 out of 10, Excellent, (46 reviews)
"Beautiful property and rooms great bar and restaurant "
United States
ANDREW
The price is AED 871
AED 1,151 total
includes taxes & fees
16 Jun - 17 Jun
Pocketbook Hotel and Bath
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.
View all properties

Top Great Barrington Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"The Red Lion Inn has so much history and character, it was a wonderful Experience to say the least. With modern amenities, it still Managed to keep its old world charm Food at the Wolf Den Tavern offered some of the best clam chowder I have ever had Enjoyed the hot tub but both hot tub and pool were difficult getting in and out of for someone with mobility issues like me Breakfast in the main dining room was also wonderful with very pleasant staff Upon check in, the only employee at the registration desk was on the phone with a customer for a good 15-20 minutes while the line behind me were all waiting to check in. Since check in time is 4:00, and we were there at 4:30 it seems like there should be more than one employee checking in customers Overall a wonderful stay. One that I would happily do again"
Diane 1-night trip
Posted 4 hours ago
The Red Lion Inn

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Frequently asked questions

Searching for hotels with bars in Great Barrington?
Great Barrington features 157 hotels and other accommodations to choose from, and likely many will have a bar where you can enjoy a beer after a day out and about exploring. While you're here, you can check out Housatonic River Walk and Housatonic River.
What are the best hotels with bars in Great Barrington?
Here's a few of the top Great Barrington accommodations with bars: Prospect Berkshires: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. Gedney Farm: Hotel with restaurant. Enjoy the bar, free breakfast, and free WiFi. The Old Inn On The Green: Inn with restaurant. Enjoy the bar, free breakfast, and free WiFi.
What is there to do in Great Barrington?
Consider a visit to Housatonic River Walk, Housatonic River, and Mahaiwe Performing Arts Center, and then find a cozy spot for a nightcap. Other places to see include Lake Mansfield Park and Ski Butternut. Great Barrington is widely-known for its top-notch restaurants.
When is the best time to visit Great Barrington?
Visiting local bars in Great Barrington is better in good weather. These rainfall averages and temperatures can help you choose the best time for bar hopping. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Great Barrington are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
How can I get to Great Barrington and around the area?
Here are some of your transportation choices in and around Great Barrington: Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 16.2 mi (26.1 km) away from the city center. You can also search for flights into Hudson, NY (HCC-Columbia County), which is 19.2 mi (30.9 km) away. If you'd like to venture out around the area, you may want a rental car for your journey.