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

Pittsfield Hotel Guide - Family Friendly Hotels in Pittsfield, Massachusetts

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Check availability on Pittsfield Family Friendly Hotels

Our top choices for Pittsfield family-friendly hotels

Lobby sitting area

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, (1,004 reviews)
  • cleanliness
    Berkshire family fun with free breakfast and ski-area adventures just minutes from winter sports and hiking trails.
The price is €132
includes taxes & fees
13 Jul - 14 Jul
Best Western Plus Berkshire Hills Inn & Suites
Exterior

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (925 reviews)
The price is €91
includes taxes & fees
26 Jul - 27 Jul
Cozy Corner Motel
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, (127 reviews)
  • cleanliness
    Splash into family fun with indoor pool and hot tub—just minutes from Bousquet Ski Area and Tanglewood Music Centre.
The price is €149
includes taxes & fees
16 Jul - 17 Jul
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
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, (1,011 reviews)
The price is €123
includes taxes & fees
12 Jul - 13 Jul
Comfort Inn & Suites East Greenbush - Albany
Exterior detail

Williamstown Motel

Williamstown Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (330 reviews)
The price is €97
includes taxes & fees
13 Jul - 14 Jul
Williamstown Motel
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (848 reviews)
The price is €61
includes taxes & fees
26 Jul - 27 Jul
FairBridge Inn Express
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, (1,012 reviews)
  • cleanliness
    Family adventures await with a heated indoor pool, kid-friendly dining, and spacious suites in the heart of Pittsfield.
The price is €139
includes taxes & fees
3 Aug - 4 Aug
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Miscellaneous

1896 House Country Inn & Motels

1896 House Country Inn & Motels
2.5 star property
Williamstown
6.6 out of 10, (452 reviews)
The price is €104
includes taxes & fees
15 Jul - 16 Jul
1896 House Country Inn & Motels
In-room safe, desk, free cots/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, (592 reviews)
  • cleanliness
    Escape with the kids to this quiet, comfortable motel where family stays come with free beds and cots in immaculately clean rooms.
The price is €97
includes taxes & fees
19 Jul - 20 Jul
Travelodge by Wyndham Great Barrington Berkshires
Lobby lounge

Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (28 reviews)
The price is €215
includes taxes & fees
22 Jul - 23 Jul
Element by Marriott Lenox 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.
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Choose what matters most at family-friendly hotels in Pittsfield

Pool
Breakfast included

Top Pittsfield Hotel Reviews

The Yankee Inn

The Yankee Inn

8/10 Good
"The hotel is a few minutes from Tanglewood and the Berkshire hotspots. Super friendly staff. Very accommodating. The place is a bit dated, but that has a retro charm like places on the Cape. The grounds are lovely. The breakfast is like other hotel breakfast. Lots of options: cereal, oatmeal, eggs, sausage, hard boiled eggs, fruit, bread, pastries, etc. My only complaint was the bed, which had a mattress in desperate need of replacement. We referred to it as sleeping in the valley because it made us roll to the center. It was also really high, which was challenging in an accessible room. I called and they had a stool for me within 5 minutes so we made it work. The people were so nice so I hate adding a complaint in my review. We would have asked for a room change but were there over a holiday weekend and I was pretty sure there wouldn’t be another option. The pluses outweigh the negatives so we had a good time."
Jean 3-night trip
Posted 7 hours ago
The Yankee Inn

Frequently asked questions

What's Pittsfield like for family-friendly holidays?
If you've been thinking about a trip with your children, the historic destination of Pittsfield is a good choice. The cycling 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 centre.
What's the best family accommodation in 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 good options 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 holiday in Pittsfield?
The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Pittsfield are January, March, February and November, with each month seeing an average of 18 cm 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 that you and your family will enjoy exploring while you are staying in Pittsfield. Make sure that you have lots of time for activities such as Berkshire Athenaeum and Crane Museum of Papermaking.
What's the best way for us to get around Pittsfield?
To venture out into the surrounding area, ride one of the trains from Pittsfield Intermodal Transportation Center or Pittsfield Station. Pittsfield might not have very many public transport options to choose from, so consider renting a car to explore more.