Find Hotels with Bars in Pittsfield, MA

Start date: Check-in selected.
To Date
End date: Check-out

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Pittsfield Hotels with Bars

Our top choices for Pittsfield hotels with a bar

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, (983)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
$88 nightly
The price is $99
Dec 12 - Dec 13
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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
$103 nightly
The price is $115
Dec 21 - Dec 22
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
Front of property - evening/night
Hotel On North

Hotel On North

3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (805)
"Clean room and staff was super friendly"
United States
Yuen
$149 nightly
The price is $166
Dec 11 - Dec 12
Total with taxes and fees
Hotel On North
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
$131 nightly
The price is $146
Dec 16 - Dec 17
Total with taxes and fees
Element Lenox Berkshires
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1008)
"Great stay!"
United States
Ann
$89 nightly
The price is $100
Dec 17 - Dec 18
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham
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
$250 nightly
The price is $280
Dec 14 - Dec 15
Total with taxes and fees
Prospect Berkshires
Exterior
Cozy Corner Motel

Cozy Corner Motel

2.0 star property
Williamstown
9.2 out of 10, Wonderful, (884)
"Clean, Great Staff, Quiet"
United States
john
$79 nightly
The price is $88
Dec 11 - Dec 12
Total with taxes and fees
Cozy Corner Motel
Exterior
Willows Motel Williamstown

Willows Motel Williamstown

2.0 star property
Williamstown
9.0 out of 10, Wonderful, (992)
"Very friendly staff and fresh fruit at breakfast!"
United States
Justin
$85 nightly
The price is $95
Dec 11 - Dec 12
Total with taxes and fees
Willows Motel Williamstown
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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

3.5 star property
South Lee
9.0 out of 10, Wonderful, (797)
"Place was great!"
United States
Benjamin
$120 nightly
The price is $134
Dec 11 - Dec 12
Total with taxes and fees
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Interior
Berkshires Untold

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (811)
"Easiest check in and out. Great food in dining room. "
United States
William
$113 nightly
The price is $126
Dec 14 - Dec 15
Total with taxes and fees
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.
View all properties

Top Pittsfield Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Clean spacious toom"
Daniel 2-night trip
Posted 3 days ago
Vacation Village in the Berkshires

Frequently asked questions

Searching for hotels with bars in Pittsfield?
Pittsfield offers 74 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.
What is there to do in Pittsfield?
If you have time to explore, consider visiting Berkshire Museum, Colonial Theater, and Bousquet Ski Area, and then find a cozy spot for a nightcap. Other places to see include Hancock Shaker Village and Housatonic River. 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.

Explore a world of travel with Expedia