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Our top choices for Pittsfield family-friendly hotels

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, (1,000 reviews)
  • cleanliness
    Berkshire family fun with free breakfast and ski-area adventures just minutes from winter sports and hiking trails.
The price is NT$3,395
NT$3,792 total
includes taxes & fees
Mar 26 - Mar 27
Best Western Plus Berkshire Hills Inn & Suites

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (87 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 NT$4,204
NT$4,696 total
includes taxes & fees
Apr 6 - Apr 7
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (1,000 reviews)
  • cleanliness
    Family adventures await with a heated indoor pool, kid-friendly dining, and spacious suites in the heart of Pittsfield.
The price is NT$3,690
NT$4,122 total
includes taxes & fees
Mar 20 - Mar 21
Holiday Inn & Suites Pittsfield-Berkshires by IHG

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (814 reviews)
The price is NT$2,264
NT$2,529 total
includes taxes & fees
Apr 2 - Apr 3
FairBridge Inn Express

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (896 reviews)
The price is NT$2,522
NT$2,973 total
includes taxes & fees
Mar 23 - Mar 24
Cozy Corner Motel

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (598 reviews)
The price is NT$3,153
NT$3,522 total
includes taxes & fees
Mar 23 - Mar 24
Maple Terrace Motel

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (573 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 NT$2,389
NT$2,668 total
includes taxes & fees
Mar 21 - Mar 22
Travelodge by Wyndham Great Barrington Berkshires

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Family fun at lakeside retreat with kayaking, fishing, and premium TV channels.
The price is NT$3,027
NT$3,381 total
includes taxes & fees
Apr 6 - Apr 7
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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.

Choose what matters most at family-friendly hotels in Pittsfield

Top Pittsfield Hotel Reviews

Frequently asked questions

What's Pittsfield like for family-friendly vacations?
The historic destination of Pittsfield is a good choice if you've been thinking about a trip with your kids. The biking trails, entertainment, and lake views are just some of the things that make this a good place for family vacations. 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 & Suites Pittsfield-Berkshires by IHG is a hotel with an indoor pool and a restaurant, 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 Express & 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?
Colonial Theater, Bousquet Ski Area, and Berkshire Athenaeum 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 Barrington Stage Company.
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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