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

Find Hotels with Bars in Great Barrington, MA

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Great Barrington Hotels with Bars

This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

Our top choices for Great Barrington hotels with a bar

A wooden boat on calm water with a house in the background.

1. Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
10.0 out of 10, Exceptional, (48 reviews)
"Great stay!"
United States
Conor
The price is NT$9,238
NT$11,411 total
includes taxes & fees
Nov 11 - Nov 12
Prospect Berkshires
A white two-story house with a front door, windows, and a chimney.

2. The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (95 reviews)
"Lovely property.unique historic buildings and rooms with updated amenities! Quiet and peaceful beautiful dinner!"
United States
mary ellen
The price is NT$9,450
NT$11,403 total
includes taxes & fees
Nov 3 - Nov 4
The Old Inn On The Green
A straw hat, sunglasses, and two drinks on a striped towel by a body of water.

3. The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,003 reviews)
"Enjoyed staying in the old hotel and loved the large porch with the bar to relax on."
United States
Mallory
The price is NT$5,252
NT$7,486 total
includes taxes & fees
Nov 4 - Nov 5
The Red Lion Inn
A tranquil stream with rocks and trees, a building with balconies and a red railing, and a clear sky.

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

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
3.5 star property
South Lee
9.2 out of 10, Wonderful, (1,007 reviews)
"Nice place to stay"
United States
Michael
The price is NT$3,814
NT$4,898 total
includes taxes & fees
Oct 29 - Oct 30
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A house with a stone patio and wooden stools.

5. Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.6 out of 10, Exceptional, (150 reviews)
"Beyond amazing, we loved it so much!"
United States
Stacy
The price is NT$4,956
NT$5,551 total
includes taxes & fees
Nov 2 - Nov 3
Little Cat Lodge
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

6. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (682 reviews)
"Great stay!"
United States
Vandhana
The price is NT$4,095
NT$4,574 total
includes taxes & fees
Nov 1 - Nov 2
Courtyard by Marriott Lenox Berkshires
A modern building with a dark exterior, outdoor seating area with wooden chairs, and string lights.

7. the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (289 reviews)
"Super cute, fairly clean and such a lovely breakfast!"
United States
Luis
The price is NT$5,377
NT$6,022 total
includes taxes & fees
Nov 20 - Nov 21
the Alander
Two Adirondack chairs facing a river with a forested hill in the background.

8. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,007 reviews)
"The location was good for our trip."
United States
Basil
The price is NT$3,456
NT$3,860 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.

9. Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,054 reviews)
"A very good place to stay"
United States
Madhavi R
The price is NT$4,244
NT$4,741 total
includes taxes & fees
Nov 1 - Nov 2
Berkshires Untold
A hotel patio with outdoor seating and a fire pit.

10. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (715 reviews)
"Great place to stay. Great staff and convenient location. Nice restaurant as well."
United States
James
The price is NT$3,869
NT$4,322 total
includes taxes & fees
Nov 15 - Nov 16
Hilton Garden Inn Lenox Pittsfield
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.
View all properties

Top Great Barrington Hotel Reviews

Hotel On North

Hotel On North

10/10 Excellent
"Very large room and bathroom. Had parking easily accessible, very nice and helpful staff."
Gaby 2-night trip
Posted 12 hours ago
Hotel On North

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.

Explore a world of travel with Expedia