Family friendly Hotels, Pittsfield Massachusetts

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

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Our top choices for Pittsfield family-friendly hotels

In-room safe, individually decorated, individually furnished, desk

Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

Berkshire family fun with free breakfast and ski-area adventures just minutes from winter sports and hiking trails.

P8,163 total

includes taxes & fees

Jun 29 - Jun 30

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Pittsfield

Splash into family fun with indoor pool and hot tub—just minutes from Bousquet Ski Area and Tanglewood Music Center.

P11,711 total

includes taxes & fees

Jul 6 - Jul 7

Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

Pittsfield

P4,253 total

includes taxes & fees

Jul 12 - Jul 13

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Family adventures await with a heated indoor pool, kid-friendly dining, and spacious suites in the heart of Pittsfield.

P10,204 total

includes taxes & fees

Jun 29 - Jun 30

Cozy Corner Motel

Williamstown

P6,356 total

includes taxes & fees

Jul 12 - Jul 13

Comfort Inn & Suites East Greenbush - Albany

Castleton-on-Hudson

P9,126 total

includes taxes & fees

Jul 12 - Jul 13

Williamstown Motel

Williamstown

P6,095 total

includes taxes & fees

Jun 30 - Jul 1

Maple Terrace Motel

Williamstown

P8,834 total

includes taxes & fees

Jun 29 - Jun 30

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Choose what matters most at family-friendly hotels in Pittsfield

Pool

Breakfast included

Top Pittsfield Hotel Reviews

Berkshire Inn

8/10 Good

"Clean room, nice staff, only complaint was curtains were long which hung over ac and was annoying."

Quality Inn Lee - Lenox South

8/10 Good

"All in all, it was a good value, but there was a male employee who was working when I checked in and whose behavior was similar to multiple people. I was ignored for over 10 minutes while he spoke on the phone. He issued me a card without asking for my ID and when I brought multiple packages in on a carrier, he gave me a second floor room where there’s no elevator. He was indifferent. he ignored us and I didn’t appreciate that."

Frequently asked questions

What's Pittsfield like for family-friendly vacations?

If you've been thinking about a trip with your kids, the historic destination of Pittsfield is a good choice. The biking trails, entertainment, and lake views are just some of the things that make this the perfect spot for family trips. Take to the air and fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is the closest airport, or Hudson, NY (HCC-Columbia County), which is located 25.7 mi (41.4 km) from the city center.

What's the best hotel when traveling with kids to Pittsfield?

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG is a hotel with an indoor pool and free parking, and it's a top choice on Expedia for families. Other choices for your family trip include Best Western Plus Berkshire Hills Inn & Suites and Holiday Inn & Suites Pittsfield-Berkshires by IHG.

When's the best time to book a family-friendly vacation in Pittsfield?

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 there to see and do with your family in Pittsfield?

Berkshire Athenaeum, Colonial Theater, and Barrington Stage Company are interesting attractions you and your family will enjoy exploring while you are staying in Pittsfield. Make sure you have lots of time for activities like Bousquet Ski Area and Crane Museum of Papermaking.

What's the best way for us to get around Pittsfield?

To see more of the surrounding area, ride one of the trains from Pittsfield Intermodal Transportation Center or Pittsfield Station. Pittsfield might not have many public transit options so consider renting a car to explore more.

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Treat yourself

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Check availability on Pittsfield Family friendly Hotels

Our top choices for Pittsfield family-friendly hotels

Best Western Plus Berkshire Hills Inn & Suites