Find Hotels with Bars in Pittsfield, MA

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Check availability on Pittsfield Hotels with Bars

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, (674 reviews)
" Nice staff - beautiful hotel!"
United States
MARY
The price is AED 480
AED 536 total
includes taxes & fees
26 Apr - 27 Apr
Hilton Garden Inn Lenox Pittsfield
Property entrance

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (843 reviews)
"The hotel was even more beautiful in person! Rooms were incredibly spacious and lovely. The staff was incredibly friendly and helpful. Great stay would definitley return. "
United States
Alessandra
The price is AED 547
AED 611 total
includes taxes & fees
21 Apr - 22 Apr
Hotel On North
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)
"Nice property. Breakfast buffet was good. Parking lot was under construction, but complimentary valet parking was offered. Friendly staff, comfortable beds.resturanton 2 nd floor was good "
United States
D
The price is AED 459
AED 513 total
includes taxes & fees
23 Apr - 24 Apr
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (901 reviews)
"This was a great stay! The room and hotel itself were up to date and was overall a great location to check out the Berkshires. We ate one night at the hotel too and the dinner was really good! I recommend the mushroom ravioli, would stay again."
United States
Payton
The price is AED 288
AED 322 total
includes taxes & fees
27 Apr - 28 Apr
Berkshires Untold
Lobby lounge

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (25 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is AED 555
AED 620 total
includes taxes & fees
26 Apr - 27 Apr
Element Lenox Berkshires
Gazebo

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (899 reviews)
"We love Cozy Corner. It's a snug, safe, well-maintained, home away from home. Love the ample breakfast and the genuine welcome we receive every time."
United States
Ann
The price is AED 291
AED 343 total
includes taxes & fees
28 Apr - 29 Apr
Cozy Corner Motel
Dining room

Gregory House Country Inn

Gregory House Country Inn
3.0 star property
Averill Park
9.0 out of 10, Wonderful, (92 reviews)
"The entire staff are very gracious hosts and very friendly. It is always a great pleasure to visit there. Dinner and Sunday Brunch food was excellent!"
United States
Richard
The price is AED 384
AED 427 total
includes taxes & fees
20 Apr - 21 Apr
Gregory House Country Inn
Property grounds

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (1,002 reviews)
"Clean and cozy room, friendly staff, and fresh fruit for breakfast. Great location right next to Williams College."
United States
Phebe
The price is AED 297
AED 331 total
includes taxes & fees
20 Apr - 21 Apr
Willows Motel Williamstown
Miscellaneous

1896 House Country Inn & Motels

1896 House Country Inn & Motels
2.5 star property
Williamstown
6.6 out of 10, (450 reviews)
"Place was convenient, cleaned and quiet a little old, but all in all a good stay"
United States
Kelley
The price is AED 355
AED 397 total
includes taxes & fees
3 May - 4 May
1896 House Country Inn & Motels
Exterior

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,000 reviews)
"As always, our stay at The Red Lion Inn was memorable. Everything was top notch."
United States
Gary
The price is AED 502
AED 725 total
includes taxes & fees
30 Apr - 1 May
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

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

10/10 Excellent
"Limited breakfast "
jennifer 1-night trip
Posted 3 days ago
Courtyard by Marriott Lenox Berkshires

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Frequently asked questions

Searching for hotels with bars in Pittsfield?
Pittsfield offers 71 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: 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 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.