TOP Family-Friendly Hotels in Pittsfield, MA for 2026

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Our top choices for Pittsfield family-friendly hotels

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | 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.

₹12,613 total

includes taxes & fees

29 Jun - 30 Jun

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 Centre.

₹18,095 total

includes taxes & fees

6 Jul - 7 Jul

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

FairBridge Inn Express

Pittsfield

₹5,993 total

includes taxes & fees

8 Jul - 9 Jul

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.

₹13,431 total

includes taxes & fees

30 Jun - 1 Jul

Econo Lodge Lee - Great Barrington

Lee

Family-friendly budget escape with free miniature golf and breakfast, minutes from Berkshire Botanical Garden.

₹9,804 total

includes taxes & fees

12 Jul - 13 Jul

Cozy Corner Motel

Williamstown

₹9,815 total

includes taxes & fees

12 Jul - 13 Jul

Williamstown Motel

Williamstown

₹10,470 total

includes taxes & fees

5 Jul - 6 Jul

In-room safe, desk, free cots/infant beds, free rollaway beds

Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Escape with the kids to this quiet, comfortable motel where family stays come with free beds and cots in immaculately clean rooms.

₹8,360 total

includes taxes & fees

25 Jun - 26 Jun

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Choose what matters most at family-friendly hotels in Pittsfield

Pool

Breakfast included

Top Pittsfield Hotel Reviews

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent

"The room was very clean and comfortable. We stayed on the first floor, which was especially helpful since my husband is a senior. The staff was professional, kind, and welcoming throughout our stay. Breakfast was included and offered several options that worked for us as vegans. I always bring my own plant-based milk, which allows me to enjoy even more of the breakfast offerings. We especially loved the fresh fruit. The location is excellent, with a gas station conveniently located next door, pleasant areas for walking nearby, and a dog-friendly atmosphere. We were so pleased with our experience that we plan to bring our dog with us next time. We highly recommend this hotel and would gladly stay here again."

Hilton Garden Inn Lenox Pittsfield

10/10 Excellent

"Beds were extremely comfortable. Thai fusion restaurant, Jae’s, in lobby, was delicious. Bartenders were efficient and friendly. Location is 5 minute drive to downtown Lenox and Tanglewood and a 1 minute walk to Guidos, the best small specialty market (gifts, garden, fresh seafood, butcher, deli, liquors) we have ever experienced."

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good

"Property is adequate, though rundown. The building is undergoing renovations, and hopefully, a better hotel will emerge. The suite was clean with nice views of the surrounding area, but the living room area was dated, and the kitchen was undersized. We did not utilize the pool or the restaurant. Overall, I would rank the hotel as good, but be aware that construction is ongoing. Location is very good, within walking distance to several restaurants and stores."

Quality Inn Great Barrington

8/10 Good

"Room was clean and comfy except for the window A/C unit which quit working about an hour after we turned it on. Opened the windows later at night which helped some, but not a perfect temperature. Did not try the morning continental breakfast because we slept in too late and had to be home by a certain time for a gathering."

Frequently asked questions

What's Pittsfield like for family-friendly holidays?

If you've been thinking about a trip with your children, the historic destination of Pittsfield is a good choice. The cycling 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 centre.

What's the best family accommodation in 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 good options for your family trip include Holiday Inn & Suites Pittsfield-Berkshires by IHG and Best Western Plus Berkshire Hills Inn & Suites.

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

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 there to see and do with your family in Pittsfield?

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

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

To venture out into the surrounding area, ride one of the trains from Pittsfield Intermodal Transportation Center or Pittsfield Station. Pittsfield might not have very many public transport options to choose from, so consider renting a car to explore more.

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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