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Check availability on Great Barrington Hotels with a Bar

Top Great Barrington Hotels with a Bar

Egyptian cotton sheets, premium bedding, down duvets, 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 ₹23,398
₹29,151 total
includes taxes & fees
21 Dec - 22 Dec
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 ₹16,690
₹18,309 total
includes taxes & fees
8 Dec - 9 Dec
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 ₹27,443
₹33,116 total
includes taxes & fees
9 Dec - 10 Dec
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 ₹11,787
₹13,166 total
includes taxes & fees
15 Dec - 16 Dec
Element Lenox Berkshires
Corner Studio | In-room safe, blackout curtains, 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 ₹21,054
₹27,858 total
includes taxes & fees
28 Dec - 29 Dec
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 ₹8,030
₹8,970 total
includes taxes & fees
16 Dec - 17 Dec
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, (982)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is ₹8,261
₹9,228 total
includes taxes & fees
12 Dec - 13 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Outdoor pool, pool 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 ₹13,718
₹19,344 total
includes taxes & fees
5 Jan - 6 Jan 2026
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 ₹9,287
₹10,374 total
includes taxes & fees
14 Dec - 15 Dec
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 ₹9,866
₹11,020 total
includes taxes & fees
16 Dec - 17 Dec
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

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Staff were awesome. Will stay again."
Kim 2-night trip
Posted 5 days ago
The Yankee, Trademark Collection by Wyndham

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Frequently asked questions

Searching for hotels with bars in Great Barrington?
Great Barrington features 139 properties to choose from, and likely many will have a bar where you can enjoy an evening cocktail after exploring the city. 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 are some of the top Great Barrington properties 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 cosy spot for a nightcap. Other places to see include Lake Mansfield Park and Ski Butternut. Great Barrington is well known for its top-notch restaurants.
When is the best time to visit Great Barrington?
Visiting local bars in Great Barrington is better when the weather is good. These rainfall averages and temperatures can help you decide the best time for bar-hopping. The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Great Barrington are January, March, February and November, with each month seeing an average of 18 cm 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) from the city centre. Otherwise, you can search for flights to 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.