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
12 Oct - 13 Oct
Tomorrow
13 Oct - 14 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 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 deck with a dog silhouette against a backdrop of autumn foliage.
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
AED 1,041
AED 1,286 total
includes taxes & fees
10 Nov - 11 Nov
Prospect Berkshires
A rustic wooden building labeled 'GEDNEY FARM' with a signboard indicating 'SERVING DINNER WED-FRI 5:00-9:00pm'.
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.
A rustic barn-style venue with round tables and chairs, string lights, and a central bar area.

2. Gedney Farm

Gedney Farm
Great Barrington
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 brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.

4. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Stephan
AED 579
AED 829 total
includes taxes & fees
3 Nov - 4 Nov
The Red Lion Inn
A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.
A house with a stone patio and wooden stools.
A wooden fire pit surrounded by six Adirondack chairs in a forested area.
A poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.

5. Little Cat Lodge

Little Cat Lodge
Copake Falls
United States
Kees
AED 525
AED 588 total
includes taxes & fees
12 Nov - 13 Nov
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 hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.

6. 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 430
AED 552 total
includes taxes & fees
22 Oct - 23 Oct
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.
A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.

7. 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 modern bathroom with a freestanding bathtub, a fireplace, and two framed posters 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.
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.

8. The Yankee Inn

The Yankee Inn
Lenox
United States
Basil
AED 389
AED 435 total
includes taxes & fees
1 Nov - 2 Nov
The Yankee Inn
A snow-covered outdoor area with a patio, seating, and a covered dining area.
A modern living room with a fireplace, comfortable seating, and a large window with curtains.
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 Kingdom
judith
AED 564
AED 647 total
includes taxes & fees
27 Oct - 28 Oct
The Cornell Inn, Lenox & The Berkshires
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.
An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".
A spacious bar area with a long counter and multiple stools, a seating area with a sofa and chairs, and a view through large windows to the outdoors.
A cozy library with bookshelves, a fireplace, and comfortable seating.

10. Berkshires Untold

Berkshires Untold
Lenox
United States
Madhavi R
AED 478
AED 534 total
includes taxes & fees
1 Nov - 2 Nov
Berkshires Untold
View all properties

Top Great Barrington Hotel Reviews

Hotel On North

Hotel On North

10/10 Excellent
"Cool property. Very clean. Every room is unique, which makes it fun."
Elizabeth 1-night trip
Posted 5 hours ago
Hotel On North
The Red Lion Inn

The Red Lion Inn

8/10 Good
"We had a nice stay at the Red Lion Inn. Our room was clean and had a fireplace, but did not have a mini-refrigerator and the TV was placed to the side of the bed. The restaurant charged a lot ($65 for a filet mignon entree) and the food was not up to that price. The bread and salad were a la carte. The whole place seemed in need of a refresh."
Patricia 1-night trip
Posted 6 hours ago
The Red Lion Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"First, this is an absolutely gorgeous place! The outside areas are beautiful with comfy furniture, flowers and fire pits. Inside is a small intimate restaurant and bar, plus sitting area. With books and plants, very nice. We had dinner there which was excellent, and loved cocktails and sunset outside by the fire pits. When we checked in, we were assigned one of their premium rooms, which sounded great. However, it was on the second floor, at the very end of a long outside corridor, accessible only by stairs near the lobby. There is no elevator. We did go to the room, lugging our bags and a cooler. Unpleasant, as we are somewhat older. We concluded that we did not want to be that far from the main area, so asked to be moved, and were accommodated. We found the new room the same, but lacking a luggage rack and a coffee service (those were only available in the premium rooms at the end of the long corridor). We were given a luggage rack, and complimentary coffee was available in the restaurant in the morning, but it seemed odd that those were considered premium in such a nice place. Otherwise we loved the hotel, room was very nice with a comfortable bed and a very updated bath with a walk in shower. The real star of the hotel is the lobby restaurant and outdoor space - that was just perfect!"
William 1-night trip
Posted 1 day ago
Quality Inn Great Barrington
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Clean room, very friendly and accommodating staff and free parking"
Alana 2-night trip
Posted 6 days 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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