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Check availability on Pittsfield Family-Friendly Hotels

This weekend
10 Jul - 12 Jul
Next weekend
17 Jul - 19 Jul

Our top choices for Pittsfield family-friendly hotels

Exterior

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (923 reviews)
The price is Rp1.586.799
Rp1.865.182 total
includes taxes & fees
12 Jul - 13 Jul
Cozy Corner Motel
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 Rp2.447.140
Rp2.733.441 total
includes taxes & fees
2 Aug - 3 Aug
Best Western Plus Berkshire Hills Inn & Suites
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (846 reviews)
The price is Rp1.117.489
Rp1.248.234 total
includes taxes & fees
21 Jul - 22 Jul
FairBridge Inn Express
Exterior detail

Williamstown Motel

Williamstown Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (329 reviews)
The price is Rp1.778.337
Rp1.986.402 total
includes taxes & fees
13 Jul - 14 Jul
Williamstown 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, (125 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 Rp2.979.972
Rp3.328.629 total
includes taxes & fees
12 Jul - 13 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 Rp2.276.188
Rp2.526.498 total
includes taxes & fees
12 Jul - 13 Jul
Comfort Inn & Suites East Greenbush - Albany
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, (1,011 reviews)
  • cleanliness
    Family adventures await with a heated indoor pool, kid-friendly dining, and spacious suites in the heart of Pittsfield.
The price is Rp2.735.240
Rp3.055.191 total
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, (451 reviews)
The price is Rp1.908.569
Rp2.131.873 total
includes taxes & fees
15 Jul - 16 Jul
1896 House Country Inn & Motels
Standard Room, 1 King Bed | Desk, iron/ironing board, free cots/infant beds, rollaway beds

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (675 reviews)
  • cleanliness
    Family-friendly budget escape with free miniature golf and breakfast, minutes from Berkshire Botanical Garden.
The price is Rp1.514.279
Rp1.691.449 total
includes taxes & fees
3 Aug - 4 Aug
Econo Lodge Lee - Great Barrington
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
7.4 out of 10, Good, (591 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 Rp1.778.337
Rp1.986.402 total
includes taxes & fees
19 Jul - 20 Jul
Travelodge by Wyndham Great Barrington 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.
View all properties

Choose what matters most at family-friendly hotels in Pittsfield

Pool
Breakfast included

Top Pittsfield Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent
"Great location with easy parking Excellent cleaning staff. Done promptly and right. Very helpful front desk staff."
Brian 5-night trip
Posted less than an hour 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 Best Western Plus Berkshire Hills Inn & Suites and Holiday Inn & Suites Pittsfield-Berkshires by IHG.
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.