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

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Check availability on Great Barrington Hotels with Bars

Next weekend
6 Nov - 8 Nov
In two weeks
13 Nov - 15 Nov

Our top choices for Great Barrington hotels with a bar

A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.

1. East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.6 out of 10, Exceptional, (58 reviews)
"East Rock was a nice, clean, and comfortable place to stay. Everything was great, and I enjoyed my stay."
United States
Sharon
The price is AED 452
AED 505 total
includes taxes & fees
1 Dec - 2 Dec
East Rock Inn
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

2. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
Great Barrington
9.4 out of 10, Exceptional, (819 reviews)
"Nice view and location for fall color."
United States
Md
The price is AED 528
AED 589 total
includes taxes & fees
4 Nov - 5 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

3. Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (935 reviews)
"Super clean and cozy and safe"
United States
Andrea
The price is AED 220
AED 246 total
includes taxes & fees
1 Nov - 2 Nov
Monument Mountain Motel
A Holiday Inn Express & Suites building with a clear entrance, a covered parking area, and a stone facade.

4. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (849 reviews)
"Always a pleasurable stay. The rooms are clean, the amenities are appreciated, and the staff very attentive. Great location and as a single traveler I always feel safe staying here."
United States
Cynthia
The price is AED 305
AED 341 total
includes taxes & fees
30 Nov - 1 Dec
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

5. Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Downtown Great Barrington
8.6 out of 10, Excellent, (1,002 reviews)
"Our room was spotless and the staff was helpful and welcoming!"
United States
Lynne
The price is AED 259
AED 289 total
includes taxes & fees
1 Dec - 2 Dec
Quality Inn Great Barrington
An outdoor patio with a stone table and chairs, a grill, and a stone fireplace.

6. Maya's Garden House

Maya's Garden House
2.0 star property
Great Barrington
The price is AED 3,255
AED 4,600 total
includes taxes & fees
14 Nov - 15 Nov
Maya's Garden House
A white two-story house with a front door, windows, and a chimney.

7. The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (96 reviews)
"Lovely property.unique historic buildings and rooms with updated amenities! Quiet and peaceful beautiful dinner!"
United States
mary ellen
The price is AED 1,065
AED 1,285 total
includes taxes & fees
1 Nov - 2 Nov
The Old Inn On The Green
A large house with a balcony and a grassy yard.

8. The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (637 reviews)
"A fine place for a quick overnight trip to the Berkshires."
United States
David
The price is AED 304
AED 340 total
includes taxes & fees
9 Nov - 10 Nov
The Little Lion
A hotel room with a large bed, a desk with a coffee maker, a chair, a TV, and a window with curtains.

9. Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.4 out of 10, Good, (626 reviews)
"Stay was great. Staff very friendly and helpful. 1 guest was screaming at someone at 4am but other than that it was a great stay"
United States
Sherry
The price is AED 290
AED 324 total
includes taxes & fees
1 Nov - 2 Nov
Travelodge by Wyndham Great Barrington 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.
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Top Great Barrington Hotel Reviews

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Room was clean, huge and very comfortable. Day Staff was a bit stiff and unwelcoming. Very expansive breakfast area and cozy table setups. Parking wasn’t convenient - a bit of a walk, but easy if you unload and load at the door and then park."
Michael 1-night trip
Posted 11 hours ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Frequently asked questions

Searching for hotels with bars in Great Barrington?
Great Barrington features 146 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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