Find Boutique Hotels in Pittsfield, MA

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Recommended hotels in Pittsfield

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1001)
"Very friendly and good Breakfast."
United States
Jesse
The price is NT$2,401
NT$2,682 total
includes taxes & fees
Jan 4 - 2026/1/5
Best Western Plus Berkshire Hills Inn & Suites

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (70)
"This is a brand new hotel. Everything was perfect, from check-in to check-out. We especially enjoyed the hot tub and pool. "
United States
Joan
The price is NT$3,852
NT$4,303 total
includes taxes & fees
Jan 4 - 2026/1/5
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

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, (1003)
"Room was very comfortable and it was clean. Staff were nice and helpful. Christmas decorations were lovely!"
United States
Clare
The price is NT$2,772
NT$3,097 total
includes taxes & fees
Jan 3 - 2026/1/4
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (659)
"The room was very clean with comfortable King bed. We really enjoyed the hot tub."
United States
Christine
The price is NT$4,020
NT$4,490 total
includes taxes & fees
Jan 2 - 2026/1/3
Hilton Garden Inn Lenox Pittsfield

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (796)
"Spacious room and loved pool and hot tub!"
United States
Deanna
The price is NT$3,102
NT$4,167 total
includes taxes & fees
Jan 11 - 2026/1/12
Berkshire Mountain Lodge

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (348)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is NT$2,955
NT$3,301 total
includes taxes & fees
Dec 30 - Dec 31
The Central Downtown Inn & Suites

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (840)
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
The price is NT$2,703
NT$3,019 total
includes taxes & fees
Dec 30 - Dec 31
Berkshire Inn

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (809)
"Clean room and staff was super friendly"
United States
Yuen
The price is NT$4,684
NT$5,232 total
includes taxes & fees
Dec 30 - Dec 31
Hotel On North
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.

Top Pittsfield Hotel Reviews

Frequently asked questions

What's there to see and do in Pittsfield?
The theaters and sporting events are just some of the things to enjoy while you're in the area. Experience the cultural highlights around Pittsfield with a visit to Berkshire Museum, Colonial Theater, and Barrington Stage Company. You might also like to explore more of the area and take in additional sights like Bousquet Ski Area, Hancock Shaker Village, and Crane Museum of Papermaking while you're here.
What kind of weather should I plan for when I travel to Pittsfield?
Getting an idea of what to expect from the weather in Pittsfield is important when you plan your trip. 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.
What's the best way to get to my boutique hotel in Pittsfield?
You have a few options for getting to Pittsfield. The closest major airport is Pittsfield, MA (PSF-Pittsfield Municipal), which is located 2.5 mi (4 km) from the heart of the city, but Hudson, NY (HCC-Columbia County) may also be an option. To explore the surrounding area, hop aboard a train at Pittsfield Intermodal Transportation Center or Pittsfield Station.

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