Find Hotels with Bars in Pittsfield, MA

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Check availability on Pittsfield Hotels with Bars

Top Pittsfield Hotels with Bars

Hotel On North
Food and drink

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (743)
"Great boutique hotel"
The price is SAR 709
SAR 792 total
includes taxes & fees
6 Aug - 7 Aug
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, (637)
"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 772
SAR 862 total
includes taxes & fees
17 Aug - 18 Aug
Hilton Garden Inn Lenox Pittsfield
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (822)
"Very convenient location, downtown, short drive to local attractions "
The price is SAR 483
SAR 540 total
includes taxes & fees
27 Jul - 28 Jul
Holiday Inn & Suites Pittsfield-Berkshires by IHG
The Central Downtown Inn & Suites
Microwave, oven, stovetop, dishwasher

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (298)
"Friendly staff, clean and perfect for a trip with the pups! "
The price is SAR 484
SAR 540 total
includes taxes & fees
27 Jul - 28 Jul
The Central Downtown Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1013)
"Very nice stay"
The price is SAR 475
SAR 531 total
includes taxes & fees
27 Jul - 28 Jul
Best Western Plus Berkshire Hills Inn & Suites
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 72 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. Hilton Garden Inn Lenox Pittsfield: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. Hotel On North: 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 Herman Melville's Arrowhead and Bousquet Ski Area. 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.