The Best Family Hotels in Pittsfield, MA from ₩99,841 in 2026

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

1. 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.

₩191,321 total

includes taxes & fees

Sep 2 - Sep 3

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, desk, laptop workspace, blackout drapes

2. 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.

₩189,842 total

includes taxes & fees

Aug 23 - Aug 24

3. 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.

₩229,907 total

includes taxes & fees

Sep 1 - Sep 2

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

4. FairBridge Inn Express

Pittsfield

₩99,841 total

includes taxes & fees

Aug 5 - Aug 6

5. The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

Family fun at lakeside retreat with kayaking, fishing, and premium TV channels.

₩332,962 total

includes taxes & fees

Aug 6 - Aug 7

6. Cozy Corner Motel

Williamstown

₩159,623 total

includes taxes & fees

Aug 5 - Aug 6

7. Maple Terrace Motel

Williamstown

₩207,395 total

includes taxes & fees

Aug 9 - Aug 10

8. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

Families splash into fun at this Berkshires hotel with indoor pool, game arcade, and cozy rooms—all nestled near Ski Butternut.

₩312,948 total

includes taxes & fees

Aug 17 - Aug 18

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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

8/10 Good

"Although dated, the propertyis well maintained and clean. Everything worked in the room, the bed was good and no problems occurred. No bottled water is provided and dont expect an eye popping view of the Bay, unless you are on the second floor ( we weren't). A good value for the cost, a lot cheaper than stayingin P-town or on the eastern coast. Would stay there again."

Vacation Village in the Berkshires

8/10 Good

"There were dead bugs throughout the room. We asked for a crib no fewer than four times and it wasn't delivered ever. I had to make my way to the check-in desk and bring it to my room myself. Similarly, the hairdryer broke while using it, we asked for a replacement be brought to the room, and it was... six hours later. In short, you get there, you get the key, and you are on your own. Do not expect anyone to help you."

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 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 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?

Colonial Theater, Barrington Stage Company, and Bousquet Ski Area 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 Berkshire Athenaeum 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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Change your mind

Treat yourself

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Check availability on Pittsfield Family Hotels

Our top choices for Pittsfield family-friendly hotels

1. Holiday Inn & Suites Pittsfield-Berkshires by IHG

2. Best Western Plus Berkshire Hills Inn & Suites