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Top Pittsfield Boutique Hotels

Hotel On North
Front of property – evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (753)
"Staff were excellent and welcoming."
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 theatres 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 Herman Melville's Arrowhead 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 planning your trip. 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.
What's the best way to get to my boutique hotel in Pittsfield?
You have a few options for transportation to and around 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.