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

Find Family Hotels in Pittsfield, MA

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Pittsfield Family Hotels

This weekend
Jul 31 - Aug 2
Next weekend
Aug 7 - Aug 9

Our top choices for Pittsfield family-friendly hotels

Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
7.8 out of 10, Good, (1,002 reviews)
  • cleanliness
    Family adventures await with a heated indoor pool, kid-friendly dining, and spacious suites in the heart of Pittsfield.
The price is ₩160,215
₩178,960 total
includes taxes & fees
Aug 6 - Aug 7
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, desk, laptop workspace, blackout drapes

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,010 reviews)
  • cleanliness
    Berkshire family fun with free breakfast and ski-area adventures just minutes from winter sports and hiking trails.
The price is ₩189,670
₩211,861 total
includes taxes & fees
Aug 16 - Aug 17
Best Western Plus Berkshire Hills Inn & Suites
Indoor pool

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (147 reviews)
  • cleanliness
    Splash into family fun with indoor pool and hot tub—just minutes from Bousquet Ski Area and Tanglewood Music Center.
The price is ₩208,687
₩233,103 total
includes taxes & fees
Aug 30 - Aug 31
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Desk, iron/ironing board, WiFi (free), bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (861 reviews)
The price is ₩89,585
₩100,067 total
includes taxes & fees
Aug 13 - Aug 14
FairBridge Inn Express
Exterior

Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany
2.5 star property
Castleton-on-Hudson
8.6 out of 10, Excellent, (1,001 reviews)
The price is ₩182,474
₩202,546 total
includes taxes & fees
Aug 3 - Aug 4
Comfort Inn & Suites East Greenbush - Albany
Property amenity

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
Great Barrington
9.4 out of 10, Exceptional, (798 reviews)
  • cleanliness
    Families splash into fun at this Berkshires hotel with indoor pool, game arcade, and cozy rooms—all nestled near Ski Butternut.
The price is ₩280,802
₩313,656 total
includes taxes & fees
Aug 13 - Aug 14
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Exterior

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (935 reviews)
The price is ₩136,326
₩159,985 total
includes taxes & fees
Aug 9 - Aug 10
Cozy Corner Motel
Exterior

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (628 reviews)
The price is ₩200,521
₩223,978 total
includes taxes & fees
Aug 9 - Aug 10
Maple Terrace Motel
Daily to-go breakfast for a fee

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
3.0 star property
Hancock
8.2 out of 10, Very Good, (1,004 reviews)
  • cleanliness
    Family-friendly mountain resort with pools and skiing thrills for all ages in Jiminy Peak.
The price is ₩229,373
₩256,209 total
includes taxes & fees
Aug 30 - Aug 31
Jiminy Peak Mountain Resort
In-room safe, desk, cribs (free), rollaway beds (free)

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.4 out of 10, Good, (599 reviews)
  • cleanliness
    Escape with the kids to this quiet, comfortable motel where family stays come with free beds and cribs in immaculately clean rooms.
The price is ₩142,817
₩159,527 total
includes taxes & fees
Aug 5 - Aug 6
Travelodge by Wyndham Great Barrington Berkshires
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.
View all properties

Choose what matters most at family-friendly hotels in Pittsfield

Pool
Breakfast included

Top Pittsfield Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"This was a beautiful hotel with eclectic decor, a lovely sensory room for guests, a fun gallery, coffee and breakfast, walkable neighborhood, close proximity to MASS MoCA, and friendly helpful staff. Room was super clean and comfortable. We had everything we needed for an enjoyable stay."
Amanda 1-night trip
Posted 10 hours ago
Hotel Downstreet, an Ascend Collection Hotel

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, Bousquet Ski Area, 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 Crane Museum of Papermaking and Berkshire Athenaeum.
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.