Find Hotels with Bars in Great Barrington, MA

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Check availability on Great Barrington Hotels with Bars

Top Great Barrington Hotels with Bars

Egyptian cotton sheets, premium bedding, down comforters, minibar
Prospect Berkshires

Prospect Berkshires

3.0 star property
Egremont
9.6 out of 10, Exceptional, (15)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
The price is NT$8,122
NT$10,119 total
includes taxes & fees
Dec 21 - Dec 22
Prospect Berkshires
Front of property
Gedney Farm

Gedney Farm

3.5 star property
Great Barrington
9.2 out of 10, Wonderful, (132)
"We loved our stay at Gedney. Michael was a sweetheart, and the grounds are GORGEOUS. We loved our room with fireplace - the whole setting is just country and updated/old. For anyone who loves farms and barns and rustic, this is for you. Can't wait to return."
United States
Lynda
The price is NT$5,795
NT$6,357 total
includes taxes & fees
Dec 8 - Dec 9
Gedney Farm
Room 191, 1 Queen Bed, 1 Single Bed, 1 Sofa Bed | Premium bedding, individually decorated, individually furnished
The Old Inn On The Green

The Old Inn On The Green

4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (90)
"Beautiful Inn and outstanding chef"
United States
Catherine
The price is NT$9,528
NT$11,498 total
includes taxes & fees
Dec 8 - Dec 9
The Old Inn On The Green
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
United States
joel
The price is NT$4,092
NT$4,571 total
includes taxes & fees
Dec 14 - Dec 15
Element Lenox Berkshires
Corner Studio | In-room safe, blackout drapes, iron/ironing board, free WiFi
Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2.0 star property
Hudson
8.0 out of 10, Very Good, (8)
"The room was very nice, and the staff was great"
United States
Kienan
The price is NT$7,310
NT$9,672 total
includes taxes & fees
Dec 28 - Dec 29
Pocketbook Hotel and Bath
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Great stay!"
United States
Ann
The price is NT$2,788
NT$3,114 total
includes taxes & fees
Dec 14 - Dec 15
The Yankee, Trademark Collection by Wyndham
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, (980)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is NT$2,874
NT$3,210 total
includes taxes & fees
Dec 12 - Dec 13
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1000)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is NT$4,822
NT$6,785 total
includes taxes & fees
Jan 5 - 2026/1/6
The Red Lion Inn
Terrace/patio
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (657)
"Clean and convenient to Mt. Greylock. Kind staff. "
United States
Kristen
The price is NT$3,224
NT$3,601 total
includes taxes & fees
Dec 14 - Dec 15
Hilton Garden Inn Lenox Pittsfield
Interior
Berkshires Untold

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (807)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
The price is NT$3,425
NT$3,826 total
includes taxes & fees
Dec 10 - Dec 11
Berkshires Untold
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.
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Top Great Barrington Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"I enjoyed the holiday inn. I enjoyed the staff made me fell at home. I enjoyed the comfortable atmosphere and the room was nice and clean. I enjoyed the breakfast very much. The staff was very friendly. "
Brendan 1-night trip
Posted 2 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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Frequently asked questions

Searching for hotels with bars in Great Barrington?
Great Barrington features 139 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.