Pittsfield Bar Hotel

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Check availability on Pittsfield Bar Hotel

Top Pittsfield Bar Hotel

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, (975)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is HK$723
HK$808 total
includes taxes & fees
5 Dec - 6 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Terrace/patio
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (657)
"Clean and convenient to Mt. Greylock. Kind staff. "
United States
Kristen
The price is HK$866
HK$967 total
includes taxes & fees
2 Jan - 3 Jan 2026
Hilton Garden Inn Lenox Pittsfield
Front of property – evening/night
Hotel On North

Hotel On North

3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (803)
"Clean room and staff was super friendly"
United States
Yuen
The price is HK$1,038
HK$1,160 total
includes taxes & fees
22 Dec - 23 Dec
Hotel On North
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
United States
joel
The price is HK$1,020
HK$1,139 total
includes taxes & fees
11 Dec - 12 Dec
Element Lenox Berkshires
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1014)
"Great stay!"
United States
Ann
The price is HK$487
HK$543 total
includes taxes & fees
14 Dec - 15 Dec
The Yankee, Trademark Collection by Wyndham
Exterior
Cozy Corner Motel

Cozy Corner Motel

2.0 star property
Williamstown
9.2 out of 10, Wonderful, (884)
"Clean, Great Staff, Quiet"
United States
john
The price is HK$582
HK$686 total
includes taxes & fees
3 Dec - 4 Dec
Cozy Corner Motel
Egyptian cotton sheets, premium bedding, down duvets, minibar
Prospect Berkshires

Prospect Berkshires

3.0 star property
Egremont
9.6 out of 10, Exceptional, (15)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
The price is HK$2,025
HK$2,523 total
includes taxes & fees
3 Dec - 4 Dec
Prospect Berkshires
Exterior
Willows Motel Williamstown

Willows Motel Williamstown

2.0 star property
Williamstown
9.0 out of 10, Wonderful, (991)
"Very friendly staff and fresh fruit at breakfast!"
United States
Justin
The price is HK$596
HK$665 total
includes taxes & fees
14 Dec - 15 Dec
Willows Motel Williamstown
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
South Lee
9.0 out of 10, Wonderful, (794)
"Place was great!"
United States
Benjamin
The price is HK$829
HK$1,035 total
includes taxes & fees
9 Dec - 10 Dec
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Interior
Berkshires Untold

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (806)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
The price is HK$854
HK$954 total
includes taxes & fees
9 Dec - 10 Dec
Berkshires Untold
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

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent
"Loved having coffee and tea 24/7"
Jessica 3-night trip
Posted 4 days ago
Best Western Plus Berkshire Hills Inn & Suites

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Frequently asked questions

Searching for hotels with bars in Pittsfield?
Pittsfield offers 74 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. Hilton Garden Inn Lenox Pittsfield: Hotel with restaurant. Enjoy the bar, free WiFi and free parking. Hotel On North: 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 cosy 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 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.