Find Family Hotels in Pittsfield, MA

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Top Pittsfield Family Hotels

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (744)
"Great boutique hotel"
The price is SAR 709
SAR 792 total
includes taxes & fees
4 Aug - 5 Aug
Hotel On North

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1010)
"Very nice stay"
The price is SAR 475
SAR 531 total
includes taxes & fees
27 Jul - 28 Jul
Best Western Plus Berkshire Hills Inn & Suites

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (824)
"Very convenient location, downtown, short drive to local attractions "
The price is SAR 484
SAR 540 total
includes taxes & fees
27 Jul - 28 Jul
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Berkshire Inn

2.0 star property
7.8 out of 10, Good, (783)
"The motel was nicely done and clean. The beds were comfortable "
The price is SAR 331
SAR 370 total
includes taxes & fees
20 Jul - 21 Jul
Berkshire Inn

FairBridge Inn Express

2.5 star property
5.4 out of 10, (744)
"Close to our target event a plus"
The price is SAR 267
SAR 298 total
includes taxes & fees
3 Aug - 4 Aug
FairBridge Inn Express

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (637)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is SAR 737
SAR 823 total
includes taxes & fees
27 Jul - 28 Jul
Hilton Garden Inn Lenox Pittsfield

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (298)
"Friendly staff, clean and perfect for a trip with the pups! "
The price is SAR 484
SAR 540 total
includes taxes & fees
21 Jul - 22 Jul
The Central Downtown Inn & Suites
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.

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?
Best Western Plus Berkshire Hills Inn & Suites is a hotel with free parking and free breakfast, 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 Holiday Inn Express & Suites Pittsfield - Berkshires.
How many hotels that welcome families should I expect to find in Pittsfield?
Expedia has 8 family-friendly hotels and other accommodations in Pittsfield.
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.