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

Find Hotels with Bar in Pittsfield, MA from CA $156

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Check availability on Pittsfield Hotels with Bar

Tonight
Oct 4 - Oct 5
Tomorrow
Oct 5 - Oct 6
Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18

Our top choices for Pittsfield hotels with a bar

A building entrance with a large planter with purple flowers and a small tree.
A restaurant with a large open dining area, wooden tables and chairs, and a brick wall with a colorful mural.
A library with bookshelves, a television, and two armchairs.
A lobby with a red sofa, two armchairs, a wooden table with a vase, brick walls, and an ornate ceiling.

1. Hotel On North

Hotel On North
Pittsfield
United States
Lawrence
CA $159
CA $178 total
includes taxes & fees
Nov 1 - Nov 2
Hotel On North
A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.
A spacious living room with a large sofa, a coffee table, and a fireplace.
A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.
A bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.

2. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
United States
James
CA $182
CA $204 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Lenox Pittsfield
Room
An indoor swimming pool with clear pool rules signage, multiple seating areas, and a view of the outdoors through large windows.
A hotel room with a large bed, a desk with a lamp, a television, and a view of the city.
A conference room with a whiteboard, tables, and chairs.

3. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pittsfield
United States
Debra
CA $154
CA $172 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn & Suites Pittsfield-Berkshires by IHG
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

4. The Yankee Inn

The Yankee Inn
Lenox
United States
William
CA $140
CA $156 total
includes taxes & fees
Oct 19 - Oct 20
The Yankee Inn
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.
A modern restaurant with wooden flooring, bar area, and seating arrangements.
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.
A covered outdoor area with stone pillars and a view of a road and green hills.

5. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
United States
Tracy
CA $179
CA $200 total
includes taxes & fees
Nov 1 - Nov 2
Courtyard by Marriott Lenox Berkshires
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.
A spacious bar area with a long counter and multiple stools, a seating area with a sofa and chairs, and a view through large windows to the outdoors.
A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.
A cozy library with bookshelves, a fireplace, and comfortable seating.

6. Berkshires Untold

Berkshires Untold
Lenox
United States
Madhavi R
CA $188
CA $210 total
includes taxes & fees
Nov 1 - Nov 2
Berkshires Untold
A snow-covered outdoor area with a patio, seating, and a covered dining area.
A dining area with a glass table, red walls, and framed artwork.
A modern living room with a fireplace, comfortable seating, and a large window with curtains.
A snow-covered outdoor area with a small bridge over a stream, surrounded by trees and illuminated by string lights.

7. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United States
Rosann
CA $219
CA $251 total
includes taxes & fees
Oct 27 - Oct 28
The Cornell Inn, Lenox & The Berkshires
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.
A reception area with a wooden reception desk, modern pendant lighting, and a vertical garden wall.
A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.

8. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
Lenox
United States
Kirsty
CA $215
CA $240 total
includes taxes & fees
Nov 1 - Nov 2
Element by Marriott Lenox Berkshires
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.
A covered porch with wicker furniture and hanging flower baskets.
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.

9. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Stephan
CA $224
CA $322 total
includes taxes & fees
Nov 3 - Nov 4
The Red Lion Inn
A building with a porch and multiple windows, surrounded by purple flowers.
A café with a display case, a frozen food section, and a marketplace sign.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.
A living room with a sofa, armchair, coffee table, and a patterned rug.

10. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
South Lee
United States
Jared
CA $159
CA $206 total
includes taxes & fees
Oct 7 - Oct 8
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
View all properties

Top Pittsfield Hotel Reviews

Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"The cleaning staff were friendly and helpful!"
Mayra 2-night trip
Posted less than an hour ago
Quality Inn Great Barrington
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

8/10 Good
"The staff were helpful and the room was clean. Overall the experience was good"
tuhin 1-night trip
Posted 2 hours ago
The Central Downtown Inn & Suites
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"I was pleasantly surprised by how nice it was there. The photos do not do it justice. It is a large resort with lots to do. Beautiful location, our room was amazing. Just a relaxing place to unwind and enjoy the beauty of the area."
Patricia 2-night trip
Posted 4 hours ago
Vacation Village in the Berkshires
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"24-7 coffee was great"
wayne 2-night trip
Posted 5 hours ago
Hotel Downstreet, an Ascend Collection Hotel
Hotel On North

Hotel On North

8/10 Good
"Floors creak as it's an old hotel but the room and bathroom were really spacious. The town is meh bur the hotel was nice."
Robin 2-night trip
Posted 21 hours ago
Hotel On North
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent
"My impression s? It’s a quiet rural area, but I am impressed how quiet the motel was. Not all the time, but occasionally it get noisy. I also liked the area."
Casey A 4-night trip
Posted 4 days ago
Best Western Plus Berkshire Hills Inn & Suites

Frequently asked questions

Searching for hotels with bars in Pittsfield?
Pittsfield offers 68 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: Hotel with restaurant. 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.

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