A historic building with classical architecture, a traffic light, and a yellow taxi.

Pittsfield Bar Hotel

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Check availability on Pittsfield Bar Hotel

This weekend
10 Jul - 12 Jul
Next weekend
17 Jul - 19 Jul

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, (687 reviews)
"Five Star stay!"
United States
Adeline
The price is HK$1,481
HK$1,654 total
includes taxes & fees
8 Jul - 9 Jul
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, (1,006 reviews)
"Quiet room. Comfortable bed linens"
United States
Margo
The price is HK$1,263
HK$1,410 total
includes taxes & fees
12 Jul - 13 Jul
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, (873 reviews)
"Very nice clean hotel. Close to Colonial theater. Would definitely stay there again."
United States
KEITH AND SHIRLEY
The price is HK$1,953
HK$2,181 total
includes taxes & fees
12 Jul - 13 Jul
Hotel On North
Jetted bathtub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,003 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Canada
Mark
The price is HK$998
HK$1,114 total
includes taxes & fees
7 Jul - 8 Jul
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, (110 reviews)
"Wonderful stay! Our room was beautiful - clean and cozy. I had a drink at the outside bar - it was lovely. Highly recommend staying here. It’s a hidden gem."
United States
Michelle
The price is HK$882
HK$979 total
includes taxes & fees
7 Jul - 8 Jul
Gregory House Country Inn
Gazebo

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (922 reviews)
"Very clean! Friendly staff! Will stop there again!"
United States
Theresa
The price is HK$692
HK$813 total
includes taxes & fees
12 Jul - 13 Jul
Cozy Corner Motel
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,005 reviews)
"Great lobby and dining room atmosphere!"
United States
Carin
The price is HK$1,371
HK$1,531 total
includes taxes & fees
8 Jul - 9 Jul
Berkshires Untold
Property grounds

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (1,003 reviews)
"The property was nice and the staff enthusiastic"
United States
Matt
The price is HK$633
HK$707 total
includes taxes & fees
7 Jul - 8 Jul
Willows Motel Williamstown
Restaurant

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.6 out of 10, Exceptional, (91 reviews)
"Excellent lodge, recommend."
United States
Jason
The price is HK$1,334
HK$1,494 total
includes taxes & fees
14 Jul - 15 Jul
Little Cat Lodge
Exterior

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,003 reviews)
"Great place, nice amenities and convenient location, highly recommended."
United States
Arthur
The price is HK$1,015
HK$1,168 total
includes taxes & fees
9 Jul - 10 Jul
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.
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Top Pittsfield Hotel Reviews

The Yankee Inn

The Yankee Inn

8/10 Good
"We enjoyed our stay. A little overpriced for the quality, but it was the Fourth of July."
Michelle 1-night trip
Posted 6 hours ago
The Yankee Inn

Frequently asked questions

Searching for hotels with bars in Pittsfield?
Pittsfield offers 72 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 are the best hotels with bars in Pittsfield?
Here are some of the top Pittsfield accommodation options 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, Colonial Theater and Barrington Stage Company, and then find a cosy 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 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.

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