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
Oct 20 - Oct 21
Tomorrow
Oct 21 - Oct 22
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

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 bed, a chair, and a table by a large window overlooking a lake.
A wooden wall with a white pendant light fixture.
A wooden cabin with a staircase leading to a deck, surrounded by trees and a gravel path.

1. Prospect Berkshires

Prospect Berkshires
Egremont
United States
Conor
NT$9,216
NT$11,384 total
includes taxes & fees
Nov 9 - Nov 10
Prospect Berkshires
A dining area with round tables set for two, a fireplace, and a mural on the wall.
A room with two brown leather armchairs, a wooden side table with a lamp, a potted plant, and a window with a view of a snowy landscape.
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.

2. The Old Inn On The Green

The Old Inn On The Green
Great Barrington
United States
John
NT$9,396
NT$11,338 total
includes taxes & fees
Nov 1 - Nov 2
The Old Inn On The Green
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.
A covered porch with wicker furniture and hanging flower baskets.
A bar with wooden floors and shelves filled with bottles.

3. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Mallory
NT$5,104
NT$7,311 total
includes taxes & fees
Nov 4 - Nov 5
The Red Lion Inn
A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.
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 house with a stone patio and wooden stools.
A wooden fire pit surrounded by six Adirondack chairs in a forested area.

4. Little Cat Lodge

Little Cat Lodge
Copake Falls
United States
Stacy
NT$4,928
NT$5,520 total
includes taxes & fees
Nov 12 - Nov 13
Little Cat Lodge
A building with a porch and multiple windows, surrounded by purple flowers.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.
A living room with a sofa, armchair, coffee table, and a patterned rug.
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
Michael
NT$3,791
NT$4,868 total
includes taxes & fees
Oct 27 - Oct 28
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.
A modern restaurant with wooden flooring, bar area, and seating arrangements.
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.
A covered outdoor area with stone pillars and a view of a road and green hills.

6. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
United States
Vandhana
NT$4,070
NT$4,546 total
includes taxes & fees
Nov 1 - Nov 2
Courtyard by Marriott Lenox Berkshires
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
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.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.
A swimming pool with a surrounding deck, a stone wall, and a building in the background.

7. The Yankee Inn

The Yankee Inn
Lenox
United States
Basil
NT$3,446
NT$3,849 total
includes taxes & fees
Nov 1 - Nov 2
The Yankee Inn
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.
A cozy library with bookshelves, a fireplace, and comfortable seating.
A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.
An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".

8. Berkshires Untold

Berkshires Untold
Lenox
United States
Madhavi R
NT$4,218
NT$4,712 total
includes taxes & fees
Nov 1 - Nov 2
Berkshires Untold
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 modern living room with a sofa, armchair, and coffee table. There is a bed with a headboard and pillows, a lamp, and a shelf with items.
A bar area with a green counter, two pendant lights, and shelves stocked with bottles.

9. the Alander

the Alander
Copake
United States
Luis
NT$4,536
NT$5,080 total
includes taxes & fees
Oct 30 - Oct 31
the Alander
A snow-covered outdoor area with a patio, seating, and a covered dining area.
A dining area with a glass table, red walls, and framed artwork.
A snow-covered outdoor area with a small bridge over a stream, surrounded by trees and illuminated by string lights.
A modern living room with a fireplace, comfortable seating, and a large window with curtains.

10. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United Kingdom
judith
NT$4,972
NT$5,703 total
includes taxes & fees
Oct 27 - Oct 28
The Cornell Inn, Lenox & The Berkshires
View all properties

Top Great Barrington Hotel Reviews

Hotel On North

Hotel On North

10/10 Excellent
"Well maintained and updated property. Very kind and helpful team."
Michele 1-night trip
Posted 21 hours ago
Hotel On North
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"-"
Serena 1-night trip
Posted 2 days ago
Quality Inn Great Barrington
The Little Lion

The Little Lion

10/10 Excellent
"Quaint location that is loosely tied to the Historic Red Lion Inn at Stockbridge. There is no on site staff so everything is done through texting. You do get access to the Red Lion Inn which was a wonderful "amenity" without the cost of staying there. The Little Lion is a roadside motel with about 14 or 15 units. Very clean and obviously quiet. Was a great home base for a couple of days while we tooled around the Berkshires. Would definitely book again!"
Sean 2-night trip
Posted 4 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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