Search Hotels with a Bar in Pittsfield

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Pittsfield Hotels with a Bar

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, (1,000 reviews)
"Everyone that works here is so nice! I’ve stayed here twice and had such a nice time. Thank youN"
United States
Melissa
The price is 2.575.146 ₫
2.876.543 ₫ total
includes taxes & fees
23 Jan - 24 Jan
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, (661 reviews)
" Nice staff - beautiful hotel!"
United States
MARY
The price is 3.360.942 ₫
3.754.121 ₫ total
includes taxes & fees
24 Jan - 25 Jan
Hilton Garden Inn Lenox Pittsfield
Property entrance

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (816 reviews)
"Great staff, room was huge and comfortable. "
United States
Cameron
The price is 3.915.273 ₫
4.373.281 ₫ total
includes taxes & fees
21 Jan - 22 Jan
Hotel On North
Lobby lounge

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (16 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is 3.652.503 ₫
4.079.846 ₫ total
includes taxes & fees
21 Jan - 22 Jan
Element Lenox Berkshires
Exterior

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (18 reviews)
"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 5.570.724 ₫
7.103.041 ₫ total
includes taxes & fees
27 Jan - 28 Jan
Prospect 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, (1,003 reviews)
"Everything was great! "
Canada
Daphne
The price is 2.435.027 ₫
2.719.925 ₫ total
includes taxes & fees
22 Jan - 23 Jan
The Yankee, Trademark Collection by Wyndham
Gazebo

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (890 reviews)
"Excellent service and a beautifully decorated property."
United States
Ivana
The price is 1.821.343 ₫
2.154.862 ₫ total
includes taxes & fees
1 Feb - 2 Feb
Cozy Corner Motel
Property grounds

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (1,000 reviews)
"Wonderful. Great hosts. Would 100% stay again"
United States
Ben
The price is 2.010.191 ₫
2.245.370 ₫ total
includes taxes & fees
29 Jan - 30 Jan
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, (818 reviews)
"We had a great stay! Karaoke in the bar was a blast!! Great little condo!!"
United States
Stephanie
The price is 2.956.162 ₫
3.815.747 ₫ total
includes taxes & fees
22 Jan - 23 Jan
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (835 reviews)
"Great hospitality and beautiful design. Our family had a great time!"
United States
Alison
The price is 2.319.997 ₫
2.591.437 ₫ total
includes taxes & fees
8 Feb - 9 Feb
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

Frequently asked questions

Searching for hotels with bars in Pittsfield?
Pittsfield offers 74 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, consider a visit to Berkshire Museum and Colonial Theater.
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 cosy spot for a nightcap. Other places to see include Guido's Marketplace 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 choose 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 -3°C. The snowiest months in Pittsfield are January, March, February and November, with each month seeing an average of 18 cm 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) away. You can also search for flights into Hudson, NY (HCC-Columbia County), which is 25.7 mi (41.4 km) away. To venture out into the surrounding area, ride one of the trains from Pittsfield Intermodal Transportation Center or Pittsfield Station.