Find Hotels with Bar in Pittsfield, MA from CA $125

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Check availability on Pittsfield Hotels with Bar

This weekend
May 29 - May 31
Next weekend
Jun 5 - Jun 7

Our top choices for Pittsfield hotels with a bar

Breakfast, lunch and dinner served

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (678 reviews)
"Clean room, staff was friendly and efficient. Great breakfast"
United States
Donna
The price is CA $198
CA $222 total
includes taxes & fees
May 31 - Jun 1
Hilton Garden Inn Lenox Pittsfield
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, (1,001 reviews)
"The room was comfortable, and clean. The staff was very courteous and helpful. Breakfast was adequate. Check in and check out went smoothly."
United States
Sharon
The price is CA $175
CA $196 total
includes taxes & fees
Jun 1 - Jun 2
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Property entrance

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (859 reviews)
"Very nice clean hotel. Close to Colonial theater. Would definitely stay there again."
United States
KEITH AND SHIRLEY
The price is CA $192
CA $215 total
includes taxes & fees
May 28 - May 29
Hotel On North
Superior Room, 1 King Bed, Jetted Tub | Jetted tub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,008 reviews)
"Breakfast ok, coffee good, staff great"
United States
Peter
The price is CA $192
CA $215 total
includes taxes & fees
Jun 15 - Jun 16
The Yankee Inn
Dining room

Gregory House Country Inn

Gregory House Country Inn
3.0 star property
Averill Park
9.0 out of 10, Wonderful, (95 reviews)
"Comfy, cozy, quiet stay in this lovely property full of character! Thank you, hard-working staff."
United States
Leslieann H
The price is CA $143
CA $159 total
includes taxes & fees
May 26 - May 27
Gregory House Country Inn
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (959 reviews)
"Great stay!"
United States
Aditya
The price is CA $148
CA $166 total
includes taxes & fees
Jun 8 - Jun 9
Berkshires Untold
Gazebo

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (909 reviews)
"Facilities were excellent. Staff was very helpful and very efficient & courteous in taking care of any concerns I had."
United States
Barbara J
The price is CA $109
CA $129 total
includes taxes & fees
May 31 - Jun 1
Cozy Corner Motel
Property grounds

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (1,003 reviews)
"A nice stay at an affordable price. "
United States
Brian
The price is CA $112
CA $125 total
includes taxes & fees
May 26 - May 27
Willows Motel Williamstown
Lobby lounge

Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (26 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is CA $251
CA $281 total
includes taxes & fees
Jun 1 - Jun 2
Element by Marriott Lenox Berkshires
Exterior

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,002 reviews)
"a delightful inn centrally located in charming Stockbridge"
United States
molly
The price is CA $233
CA $322 total
includes taxes & fees
Jun 4 - Jun 5
The Red Lion Inn
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.
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Top Pittsfield Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"The room was great. Had a kitchen, huge jetted tub, and private bedroom. Great area! I don't like paying resort fees for things we don't use though. It was raining and we arrived late at night. The indoor pool was amazingly crowded for 10pm. Must have been at least 25 people, including younger children. Earlier check out, 10 am, compared to usual 11:00 other places."
Margaret 1-night trip
Posted 4 hours ago
Vacation Village in the Berkshires

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 Barrington Stage Company.
What are the best hotels with bars in Pittsfield?
Here's some of the top Pittsfield accommodations with bars: Hotel On North: Enjoy the bar, free WiFi, and free parking. 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.
What is there to do in Pittsfield?
If you have time to explore, consider visiting Berkshire Museum, Barrington Stage Company, 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.

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