A large stone church with a tall bell tower and arched windows.

Find Hotels with Bars in Great Barrington, MA

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Check availability on Great Barrington Hotels with Bars

Tonight
27 Aug - 28 Aug
Tomorrow
28 Aug - 29 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sep - 6 Sep

Our top choices for Great Barrington hotels with a bar

1. Prospect Berkshires

Prospect Berkshires
Egremont
United States
Kellee
AED 1,118
AED 1,372 total
includes taxes & fees
27 Sep - 28 Sep
Prospect Berkshires

2. Gedney Farm

Gedney Farm
Great Barrington
United States
Jane
AED 861
AED 945 total
includes taxes & fees
7 Sep - 8 Sep
Gedney Farm

3. The Old Inn On The Green

The Old Inn On The Green
Great Barrington
United States
Catherine
AED 1,171
AED 1,413 total
includes taxes & fees
1 Sep - 2 Sep
The Old Inn On The Green

4. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Patricia
AED 550
AED 796 total
includes taxes & fees
8 Sep - 9 Sep
The Red Lion Inn

5. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
United States
Claudia
AED 430
AED 552 total
includes taxes & fees
31 Aug - 1 Sep
Holiday Inn Club Vacations Oak 'n Spruce Resort

6. Little Cat Lodge

Little Cat Lodge
Copake Falls
United States
Kees
AED 658
AED 737 total
includes taxes & fees
31 Aug - 1 Sep
Little Cat Lodge

7. The Yankee Inn

The Yankee Inn
Lenox
United States
Karen
AED 558
AED 624 total
includes taxes & fees
27 Sep - 28 Sep
The Yankee Inn

8. Berkshires Untold

Berkshires Untold
Lenox
United States
Christine
AED 521
AED 582 total
includes taxes & fees
7 Sep - 8 Sep
Berkshires Untold

9. the Alander

the Alander
Copake
United States
Phil
AED 624
AED 699 total
includes taxes & fees
30 Aug - 31 Aug
the Alander

10. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
United States
James
AED 544
AED 608 total
includes taxes & fees
27 Sep - 28 Sep
Hilton Garden Inn Lenox Pittsfield
View all properties

Top Great Barrington Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Great visit to Stockbridge. Can't think of a better place to stay than the iconic Red Lion Inn."
Daniel 2-night trip
Posted 11 hours ago
The Red Lion Inn
The Little Lion

The Little Lion

8/10 Good
"Clean and comfortable room for reasonable price. Central area/lobby is nice place to sit and read, relax, and/or eat breakfast (coffee provided). Also red Adirondack chairs up on hill behind rooms and small tables/chairs in front of some rooms. Can use the outdoor pool and whirl pool a few miles away at the Red Lion Inn, which is desirable feature on summer days. A few negatives. While the building and rooms are set back from the road, it’s located off a busy road that goes between Stockbridge and Great Barrington. You will hear the cars during the day. It’s also not what I would consider an “Inn” as it’s really a motel. It used to be the Briarcliff Motel before the Red Lion Inn purchased it. Any questions, requests, or comments need to contact them as the Little Lion didn’t have any full time staff and no one at front desk in the lobby when we stayed. We received text with code for room door."
Bruce 1-night trip
Posted 12 hours ago
The Little Lion
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Charming hotel with a wonderful breakfast and two lovely pools, plus a nature walk to a lake. The staff were great, really nice and helpful."
Anne 1-night trip
Posted 19 hours ago
The Yankee Inn
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"It was much better than expected. Subtle lighting in the room was a nice touch. Clean and very comfortable bedding and bathroom. Everything in the fitness room was was clean and operational. The breakfast was superb. A very enjoyable stay."
William 1-night trip
Posted 1 day ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Frequently asked questions

Searching for hotels with bars in Great Barrington?
Great Barrington features 145 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.

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