Find Hotels with Bars in Pittsfield, MA

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Check availability on Pittsfield Hotels with Bars

Top Pittsfield Hotels with Bars

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, (794)
"Walking distance from the Colonial Theater, lots of dining options, good breakfast, comfortable bed, clean room, clean hotel."
The price is SAR 409
SAR 457 total
includes taxes & fees
26 Jun - 27 Jun
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Hotel On North
Food and drink

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (736)
"Best hotel in the Berkshire! "
The price is SAR 585
SAR 654 total
includes taxes & fees
30 Jun - 1 Jul
Hotel On North
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 SAR 702
SAR 784 total
includes taxes & fees
22 Jun - 23 Jun
Hilton Garden Inn Lenox Pittsfield
The Porches Inn at Mass MoCA
Exterior

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (388)
"Phenomenal room, staff and location! We loved The Porches!!"
The price is SAR 740
SAR 910 total
includes taxes & fees
19 Jun - 20 Jun
The Porches Inn at Mass MoCA
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Exterior

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

3.5 star property
9.0 out of 10, Wonderful, (656)
"Wonderful property we’ve been coming here for years"
The price is SAR 503
SAR 614 total
includes taxes & fees
22 Jun - 23 Jun
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.2 out of 10, Wonderful, (1003)
"Friendly staff"
The price is SAR 446
SAR 499 total
includes taxes & fees
30 Jun - 1 Jul
The Yankee, Trademark Collection by Wyndham
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 SAR 1,151
SAR 1,286 total
includes taxes & fees
22 Jun - 23 Jun
Hampton Terrace Inn
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.2 out of 10, Wonderful, (609)
"Amazing place . "
The price is SAR 402
SAR 449 total
includes taxes & fees
25 Jun - 26 Jun
Berkshires Untold
Courtyard by Marriott Lenox Berkshires
Property amenity

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (557)
"Easy access to town..."
The price is SAR 634
SAR 708 total
includes taxes & fees
30 Jun - 1 Jul
Courtyard by Marriott Lenox Berkshires
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1000)
"Quiet, friendly, convenient"
The price is SAR 483
SAR 686 total
includes taxes & fees
22 Jun - 23 Jun
The Cornell Inn, Lenox & The Berkshires
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 Pittsfield?
Pittsfield offers 70 hotels and other lodging options 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, consider a visit to Berkshire Museum and Colonial Theater.
What are the best hotels with bars in Pittsfield?
Here's some of the top Pittsfield accommodations with bars: Holiday Inn & Suites Pittsfield-Berkshires by IHG: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. Hotel On North: Enjoy the bar, free WiFi, and free parking. Hilton Garden Inn Lenox Pittsfield: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking.
How many hotels with onsite bars should I expect to find in Pittsfield?
Expedia has 8 hotels with a bar in Pittsfield.
What is there to do in Pittsfield?
If you have time to explore, consider visiting Berkshire Museum, Colonial Theater, and Barrington Stage Company, and then find a cozy spot for a nightcap. Other places to see include Bousquet Ski Area and Hancock Shaker Village. Pittsfield is appreciated for its entertainment venues.
When is the best time to visit Pittsfield?
Visiting local bars in Pittsfield is more fun when you know what the weather holds. These temperatures and rainfall averages can help you determine 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 27°F. The snowiest months in Pittsfield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
How can I get to Pittsfield and around the area?
You might want to make the most of these transportation choices in and around Pittsfield: Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 2.5 mi (4 km) from the heart of the city. Otherwise, you can search for flights to Hudson, NY (HCC-Columbia County), which is 25.7 mi (41.4 km) away. To see more of the surrounding area, ride one of the trains from Pittsfield Intermodal Transportation Center or Pittsfield Station.