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

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Check availability on Great Barrington Hotels with Bars

Tonight
2 Oct - 3 Oct
Tomorrow
3 Oct - 4 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Great Barrington hotels with a bar

A lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.
A wooden cabin with a staircase leading to a deck, surrounded by trees and a gravel path.
A wooden cabin with a bed, a chair, and a table by a large window overlooking a lake.
A wooden deck with a dog silhouette against a backdrop of autumn foliage.

1. Prospect Berkshires

Prospect Berkshires
Egremont
United States
Conor
AED 1,140
AED 1,397 total
includes taxes & fees
2 Nov - 3 Nov
Prospect Berkshires
A rustic wooden building labeled 'GEDNEY FARM' with a signboard indicating 'SERVING DINNER WED-FRI 5:00-9:00pm'.
A rustic barn-style venue with round tables and chairs, string lights, and a central bar area.
An outdoor patio with wooden tables and chairs, surrounded by greenery.
A spacious living room with a fireplace, patterned armchairs, and a staircase leading to an upper level.

2. Gedney Farm

Gedney Farm
Great Barrington
United States
Terri
AED 733
AED 805 total
includes taxes & fees
2 Nov - 3 Nov
Gedney Farm
A dining area with round tables set for two, a fireplace, and a mural on the wall.
A cozy room with a fireplace, wooden walls, a bed with a patterned bedspread, and two wall-mounted lamps.
A room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.
A white two-story house with a front door, windows, and a chimney.

3. The Old Inn On The Green

The Old Inn On The Green
Great Barrington
United States
Catherine
AED 1,065
AED 1,285 total
includes taxes & fees
1 Nov - 2 Nov
The Old Inn On The Green
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A bar with wooden floors and shelves filled with bottles.
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.

4. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Stephan
AED 582
AED 832 total
includes taxes & fees
1 Nov - 2 Nov
The Red Lion Inn
A building with a porch and multiple windows, surrounded by purple flowers.
A living room with a sofa, armchair, coffee table, and a patterned rug.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.
A café with a display case, a frozen food section, and a marketplace sign.

5. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
South Lee
United States
Jared
AED 403
AED 522 total
includes taxes & fees
1 Nov - 2 Nov
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.
A poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.
A cozy room with a wooden bench, a table with a pitcher, and a sofa with patterned cushions. Large windows with yellow blinds offer a view of greenery outside.
A wooden fire pit surrounded by six Adirondack chairs in a forested area.

6. Little Cat Lodge

Little Cat Lodge
Copake Falls
United States
Kees
AED 514
AED 576 total
includes taxes & fees
2 Nov - 3 Nov
Little Cat Lodge
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.

7. The Yankee Inn

The Yankee Inn
Lenox
United States
William
AED 389
AED 435 total
includes taxes & fees
1 Nov - 2 Nov
The Yankee Inn
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.
A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.
A covered outdoor area with stone pillars and a view of a road and green hills.
A modern restaurant with wooden flooring, bar area, and seating arrangements.

8. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
United States
Tracy
AED 461
AED 515 total
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott Lenox Berkshires
A snow-covered outdoor area with a patio, seating, and a covered dining area.
A two-story house with a balcony, a brick chimney, and a porch with Adirondack chairs.
A snow-covered outdoor area with a small bridge over a stream, surrounded by trees and illuminated by string lights.
A dining area with a glass table, red walls, and framed artwork.

9. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United States
Rosann
AED 564
AED 647 total
includes taxes & fees
27 Oct - 28 Oct
The Cornell Inn, Lenox & The Berkshires
A modern building with a dark exterior, outdoor seating area with wooden chairs, and string lights.
A dog standing at a door entrance with a wooden floor and a mat with paw prints.
A dining table set with plates of food, wine glasses, and bottles, with a chandelier above and shelves above holding glasses and bottles.
A bar area with a green counter, two pendant lights, and shelves stocked with bottles.

10. the Alander

the Alander
Copake
United States
Thomas
AED 531
AED 594 total
includes taxes & fees
4 Oct - 5 Oct
the Alander
View all properties

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
"Steven was very helpful and so nice. He went above and beyond to help me find a lost item."
Rachelle 3-night trip
Posted 5 hours ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG
The Yankee Inn

The Yankee Inn

8/10 Good
"Room was nice but did not have the view I was hoping for. Another hotel property is mostly blocking views from Yankee Inn looking West; the direction rooms with balcony’s face. The location near"
Theresa 2-night trip
Posted 1 day ago
The Yankee Inn
The Little Lion

The Little Lion

10/10 Excellent
"Was in a great location and let us bring our dog. Convenient to everything we needed. Remote check for in so you do not see staff, but met all of our needs."
Julia 4-night trip
Posted 2 days ago
The Little Lion

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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