About Pittsfield

Right in the heart of The Berkshires, Pittsfield is perfectly poised for travellers looking to explore the best of this famously artsy, entreprenurial and historic part of Massachusetts. Accommodation options include simple, self-catering spots as well as hip boutique hotels, fit for a variety of tastes and budgets. Our pick of the best places to stay in Pittsfield is a laid-back gem in the centre of town — great for couples, groups or families.

Within easy reach of lovely Lenox, as well as the marvellous museums and country houses of Stockbridge and North Adams, Pittsfield is ideal for an active trip. Visit the Norman Rockwell Museum, the Chesterwood Estate, Edith Wharton's home, and the fascinating Hancock Shaker Village Museum if you're into heritage and culture. Pittsfield is home to the Berkshire Museum, the Lichtenstein Center for the Arts, independent Beacon Cinema and some top-notch theatre companies. There's a brilliant programme of lively artistic and musical events in the area — do find out what's on during your visit! The Tanglewood Music Festival and the Berkshire International Film Festival are particular standouts.

Expect myriad cycling and hiking trails in the surrounding Berkshire Hills, as well as opportunities to go swimming, fishing, kayaking and boating on nearby Lake Onota or Pontoosuc Lake. The region is also known for its excellent golf courses, horse riding and scenic state parks, including October Mountain State Forest. Zoar Outdoor is a family favourite for rock climbing, zip-lining and river rafting. Visit during the winter for skiing and snowshoeing in the mountains.

The best places to stay in Pittsfield fill up fast during the summer months. Book your trip well in advance to avoid missing out!

The Best Places to Stay in Pittsfield

For boutique chic

  • Hotel on North is a vibrant boutique property set within a pair of carefully restored1880s buildings. Original features fuse with whimsical artwork and modern tech to create comfortable, characterful spaces for couples, groups or families. Highlights include great cocktails and fresh, seasonal dishes, as well as a dedicated kids' play area for little ones. Funky and well-placed for discovering Pittsfield.

For an apartment or holiday cottage

  • If you'd prefer a self-catering option, we suggest that you visit our online partner Booking.com.

Travel information

  • Fly to Albany International Airport, an hour's drive away, or to Boston's Logan International Airport, which is just over two hours from Pittsfield. There are regular buses from both airports, but journeys can be slow.
  • The Berkshires are great for a road trip! Contact our online partner Rentalcars if you would like to hire a car.
  • Travel during the summer months (June to August) for the warmest weather, but do be aware that this is peak season. Come in the spring (April - May) or autumn (September - October) for fewer crowds and great hotel deals. Expect bitterly cold winters.

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The best hotels in Pittsfield

Hotel on North

Pittsfield (Massachusetts)

Restored 1880s building lovingly transformed into a laid-back downtown boutique hotel. Cosy rooms showcase original architectural features - exposed brick walls, tin ceilings and decorative columns - plus modern high-tech amenities. There's also contemporary dining, lounge bar and a kid's playroom.

  • Local exploring - A well-located base, there is no Berkshire attraction more than 40 min away; skiing, museums, theatre, fishing & mountain biking
  • Restaurant - Informal 'Eat on North' offers contemporary American cusine with eclectic touches, influenced by the seasons and local producers
  • Sights nearby - Learn about the area at Hancock Shaker Village living history museum, consisting of 20 buildings set over situated on 750 acres
  • Fishing
from $201 for 1 room, 1 night including taxes & fees
Check availability on Expedia