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
7 Aug - 9 Aug
Next weekend
14 Aug - 16 Aug

Our top choices for Pittsfield hotels with a bar

Jetted bathtub

1. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 reviews)
"First class staff and wonderful breakfast."
United States
Larry
The price is HK$1,235
HK$1,380 total
includes taxes & fees
5 Aug - 6 Aug
The Yankee Inn
Restaurant

2. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
7.8 out of 10, Good, (1,007 reviews)
"Lots of construction going on, but the staff was great. They valet-parked my car and had it waiting for me in the morning. The room was clean and comfortable."
United States
David
The price is HK$933
HK$1,042 total
includes taxes & fees
2 Sept - 3 Sept
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Property entrance

3. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (884 reviews)
"Beautiful room with an amazing lobby."
United States
Dragana
The price is HK$1,561
HK$1,743 total
includes taxes & fees
31 Aug - 1 Sept
Hotel On North
Breakfast, lunch and dinner served

4. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (698 reviews)
"Five Star stay!"
United States
Adeline
The price is HK$1,508
HK$1,684 total
includes taxes & fees
27 Aug - 28 Aug
Hilton Garden Inn Lenox Pittsfield
Lobby lounge

5. Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,007 reviews)
"Nice place to stay."
United States
Debra
The price is HK$1,221
HK$1,364 total
includes taxes & fees
23 Aug - 24 Aug
Berkshires Untold
Lobby

6. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (31 reviews)
"Great staff very friendly rooms very clezn"
United States
Lawrence
The price is HK$1,725
HK$1,927 total
includes taxes & fees
19 Aug - 20 Aug
Element by Marriott Lenox Berkshires
Exterior

7. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"The entire staff was amazing and the inn was beautiful, we will definitely be back"
United States
Edward
The price is HK$1,593
HK$1,833 total
includes taxes & fees
3 Sept - 4 Sept
The Cornell Inn, Lenox & The Berkshires
Gazebo

8. Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (935 reviews)
"Loved this place"
United States
Jeremy
The price is HK$741
HK$870 total
includes taxes & fees
10 Aug - 11 Aug
Cozy Corner Motel
Property amenity

9. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (643 reviews)
"Helpful staff, clean room and great facilities."
United Kingdom
Laura
The price is HK$1,660
HK$1,854 total
includes taxes & fees
19 Aug - 20 Aug
Courtyard by Marriott Lenox Berkshires
Property amenity

10. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
3.5 star property
South Lee
9.2 out of 10, Wonderful, (946 reviews)
The price is HK$1,052
HK$1,328 total
includes taxes & fees
31 Aug - 1 Sept
Holiday Inn Club Vacations Oak 'n Spruce Resort
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

Hotel On North

Hotel On North

10/10 Excellent
"Beautiful hotel. Helpful staff."
Kelly 1-night trip
Posted 2 hours ago
Hotel On North

Frequently asked questions

Searching for hotels with bars in Pittsfield?
Pittsfield offers 69 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: Holiday Inn & Suites Pittsfield-Berkshires by IHG: Hotel with restaurant. Enjoy the bar, free WiFi and free parking. Hotel On North: 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 Pontoosuc Lake. 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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