Search Hotels with a Bar in Great Barrington

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Check availability on Great Barrington Hotels with a Bar

Top Great Barrington Hotels with a Bar

Gedney Farm
Front of property

Gedney Farm

3.5 star property
9.2 out of 10, Wonderful, (120)
"Great staff. Quiet.. and an excellent chef! Unique property and well worth it!"
Gedney Farm
Prospect Berkshires
1 bedroom, blackout curtains, soundproofing, free WiFi

Prospect Berkshires

2.0 star property
8.0 out of 10, Very good, (1)
"Prospect was a wonderful stay with very friendly staff. The property is very well maintained. We had a great time with the all the lake activities. Would definitely recommend for a quick getaway "
The price is 9.154.950 ₫
11.102.600 ₫ total
includes taxes & fees
8 Jul - 9 Jul
Prospect Berkshires
The Old Inn On The Green
Room 191, 1 Queen Bed, 1 Single Bed, 1 Sofa Bed | Premium bedding, individually decorated, individually furnished

The Old Inn On The Green

4.0 star property
9.2 out of 10, Wonderful, (84)
"Beautiful room and property. Perfect weekend getaway!"
The price is 7.585.530 ₫
9.153.381 ₫ total
includes taxes & fees
26 Jun - 27 Jun
The Old Inn On The Green
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Property amenity

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
9.0 out of 10, Wonderful, (659)
"Wonderful property we’ve been coming here for years"
The price is 3.625.360 ₫
4.414.680 ₫ total
includes taxes & fees
26 Jun - 27 Jun
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (635)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is 5.138.804 ₫
5.740.153 ₫ total
includes taxes & fees
30 Jun - 1 Jul
Hilton Garden Inn Lenox Pittsfield
Hotel On North
Food and drink

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (738)
"Best hotel in the Berkshire! "
The price is 3.766.608 ₫
4.207.300 ₫ total
includes taxes & fees
30 Jun - 1 Jul
Hotel On North
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.2 out of 10, Wonderful, (1007)
"Nice place to stay. Good breakfast. "
The price is 3.295.782 ₫
3.681.336 ₫ total
includes taxes & fees
30 Jun - 1 Jul
The Yankee, Trademark Collection by Wyndham
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (797)
"Walking distance from the Colonial Theater, lots of dining options, good breakfast, comfortable bed, clean room, clean hotel."
The price is 2.851.113 ₫
3.184.694 ₫ total
includes taxes & fees
30 Jun - 1 Jul
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Hampton Terrace Inn
Exterior

Hampton Terrace Inn

4.0 star property
9.0 out of 10, Wonderful, (42)
"Beautiful historic house in a great location. Responsive owner. Great visit!"
The price is 10.329.399 ₫
11.537.852 ₫ total
includes taxes & fees
29 Jun - 30 Jun
Hampton Terrace Inn
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.2 out of 10, Wonderful, (613)
"Good Attentive Staff with Good Comfortable Room."
The price is 10.334.631 ₫
11.543.869 ₫ total
includes taxes & fees
11 Jul - 12 Jul
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.

Frequently asked questions

Searching for hotels with bars in Great Barrington?
Great Barrington features 142 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.
How many hotels with bars on site should I expect to find in Great Barrington?
Expedia has 6 hotels with a bar in Great Barrington.
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.