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

Our top choices for Great Barrington hotels with a bar

Exterior

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.8 out of 10, Exceptional, (24 reviews)
"Excellent local stay - would recommend to all"
United States
Gentian
The price is AED 1,157
AED 1,415 total
includes taxes & fees
22 Apr - 23 Apr
Prospect Berkshires
Front of property

Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.4 out of 10, Exceptional, (136 reviews)
"Beautiful property and rooms."
United States
Kara
The price is AED 568
AED 623 total
includes taxes & fees
19 Apr - 20 Apr
Gedney Farm
Breakfast, lunch, dinner served; American cuisine

The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (91 reviews)
"Beautiful Inn and outstanding chef"
United States
Catherine
The price is AED 1,120
AED 1,352 total
includes taxes & fees
19 Apr - 20 Apr
The Old Inn On The Green
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (899 reviews)
"This was a great stay! The room and hotel itself were up to date and was overall a great location to check out the Berkshires. We ate one night at the hotel too and the dinner was really good! I recommend the mushroom ravioli, would stay again."
United States
Payton
The price is AED 288
AED 322 total
includes taxes & fees
30 Apr - 1 May
Berkshires Untold
Lobby lounge

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (25 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is AED 540
AED 603 total
includes taxes & fees
22 Apr - 23 Apr
Element Lenox Berkshires
Exterior

the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (215 reviews)
"Delightful and well appointed stay! Close to so many things and very cozy."
United States
Jackie
The price is AED 514
AED 576 total
includes taxes & fees
19 Apr - 20 Apr
the Alander
Exterior

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,000 reviews)
"As always, our stay at The Red Lion Inn was memorable. Everything was top notch."
United States
Gary
The price is AED 502
AED 725 total
includes taxes & fees
30 Apr - 1 May
The Red Lion Inn
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (1,000 reviews)
"Nice property. Breakfast buffet was good. Parking lot was under construction, but complimentary valet parking was offered. Friendly staff, comfortable beds.resturanton 2 nd floor was good "
United States
D
The price is AED 448
AED 501 total
includes taxes & fees
17 May - 18 May
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.4 out of 10, Exceptional, (75 reviews)
"Nice rooms, very clean place"
United States
Padgett
The price is AED 559
AED 626 total
includes taxes & fees
20 Apr - 21 Apr
Little Cat Lodge
Breakfast, lunch and dinner served

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (674 reviews)
" Nice staff - beautiful hotel!"
United States
MARY
The price is AED 483
AED 539 total
includes taxes & fees
26 Apr - 27 Apr
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

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"A convenient location. Excellent well appointed and clean room. An excellent breakfast provided. Would stay again."
Lawrence 1-night trip
Posted 1 hour ago
The Yankee, Trademark Collection by Wyndham

Explore a world of travel with Expedia

Frequently asked questions

Searching for hotels with bars in Great Barrington?
Great Barrington features 153 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.