Family friendly Hotels in Pittsfield, Massachusetts

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Check availability on Pittsfield Family friendly Hotels

Top Pittsfield Family friendly Hotels

Hotel On North
Food and drink

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (743)
"Great boutique hotel"
The price is P10,710
P11,963 total
includes taxes & fees
Jul 21 - Jul 22
Hotel On North
Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1013)
"Very nice stay"
The price is P7,177
P8,016 total
includes taxes & fees
Jul 27 - Jul 28
Best Western Plus Berkshire Hills Inn & Suites
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (821)
"Very convenient location, downtown, short drive to local attractions "
The price is P7,298
P8,152 total
includes taxes & fees
Jul 27 - Jul 28
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Berkshire Inn
1 bedroom, desk, iron/ironing board, free WiFi

Berkshire Inn

2.0 star property
7.8 out of 10, Good, (779)
"The motel was nicely done and clean. The beds were comfortable "
The price is P5,666
P6,329 total
includes taxes & fees
Jul 20 - Jul 21
Berkshire Inn
FairBridge Inn Express
1 bedroom, desk, iron/ironing board, free WiFi

FairBridge Inn Express

2.5 star property
5.4 out of 10, (741)
"Close to our target event a plus"
The price is P4,029
P4,500 total
includes taxes & fees
Jul 29 - Jul 30
FairBridge Inn Express
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

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 P12,197
P13,625 total
includes taxes & fees
Jul 27 - Jul 28
Hilton Garden Inn Lenox Pittsfield
The Central Downtown Inn & Suites
Microwave, oven, stovetop, dishwasher

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (297)
"Friendly staff, clean and perfect for a trip with the pups! "
The price is P6,743
P7,532 total
includes taxes & fees
Jul 17 - Jul 18
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.