Find Family Hotels in Pittsfield, MA

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Check availability on Pittsfield Family Hotels

This weekend
May 29 - May 31
Next weekend
Jun 5 - Jun 7

Our top choices for Pittsfield family-friendly hotels

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk

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, (1,003 reviews)
  • cleanliness
    Berkshire family fun with free breakfast and ski-area adventures just minutes from winter sports and hiking trails.
The price is ₩164,818
₩184,102 total
includes taxes & fees
Jun 15 - Jun 16
Best Western Plus Berkshire Hills Inn & Suites
Restaurant

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, (1,001 reviews)
  • cleanliness
    Family adventures await with a heated indoor pool, kid-friendly dining, and spacious suites in the heart of Pittsfield.
The price is ₩182,998
₩204,403 total
includes taxes & fees
Jun 7 - Jun 8
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (819 reviews)
The price is ₩106,648
₩119,126 total
includes taxes & fees
Jun 11 - Jun 12
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, (1,000 reviews)
The price is ₩171,761
₩190,654 total
includes taxes & fees
Jun 21 - Jun 22
Comfort Inn & Suites East Greenbush - Albany
Exterior

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (910 reviews)
The price is ₩126,898
₩149,308 total
includes taxes & fees
Jun 3 - Jun 4
Cozy Corner Motel
In-room safe, desk, free cribs/infant beds, free rollaway beds

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (580 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 ₩112,499
₩125,661 total
includes taxes & fees
May 31 - Jun 1
Travelodge by Wyndham Great Barrington Berkshires
Lake

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 ₩189,522
₩211,692 total
includes taxes & fees
Jun 1 - Jun 2
The Black Swan Lee - Lenox, an Ascend Collection Hotel
BBQ/picnic area

Williamstown Motel

Williamstown Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (320 reviews)
The price is ₩133,498
₩149,118 total
includes taxes & fees
May 31 - Jun 1
Williamstown Motel
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.
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Choose what matters most at family-friendly hotels in Pittsfield

Pool
Breakfast included

Top Pittsfield Hotel Reviews

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent
"Everything was perfect!"
Mary 1-night trip
Posted 16 hours ago
Hampton Inn & Suites Berkshires-Lenox

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 Holiday Inn Express & 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?
Barrington Stage Company, Bousquet Ski Area, and Colonial Theater 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.