Search Family-Friendly Hotels in Pittsfield

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Pittsfield Family-Friendly Hotels

Our top choices for Pittsfield family-friendly hotels

Free daily on-the-go breakfast
Rodeway Inn Pittsfield

Rodeway Inn Pittsfield

Rodeway Inn Pittsfield
2.0 star property
Pittsfield
6.8 out of 10, (125)
"Air conditioning | Pet-friendly | Clean room | Staf"
United States
Anonymous traveller
The price is 1.618.407 ₫
1.779.924 ₫ total
includes taxes & fees
31 Dec - 1 Jan 2026
Rodeway Inn Pittsfield
Interior
The Eagles Nest Inn

The Eagles Nest Inn

The Eagles Nest Inn
3.0 star property
Louisiana
9.4 out of 10, Exceptional, (19)
"The room was great. Large and attractive!! Nice bathroom. Had all the convenience you need from TV to mini frig. "
United States
Judith
The price is 2.749.082 ₫
3.121.239 ₫ total
includes taxes & fees
17 Dec - 18 Dec
The Eagles Nest Inn
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

Top Pittsfield Hotel Reviews

Explore a world of travel with Expedia

Frequently asked questions

What's Pittsfield like for family-friendly holidays?
The destination of Pittsfield is a good option if you've been considering a getaway with the children. The entertainment, wildlife and cafes are just some of the things that make this an attractive spot for a family holiday. Fly into Quincy, IL (UIN-Quincy Regional-Baldwin Field), which is located 30.6 mi (49.3 km) from the city centre.
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 23°C, while the coldest months are January and February, with an average of 1°C. Average annual precipitation for Pittsfield is 1158 mm.
What's there to see and do with your family in Pittsfield?
While you and the family are holidaying in Pittsfield, you may want to get outside and enjoy the great outdoors at spots such as King Park, Clarksville Riverfront Park and Mississippi River. Make sure that you have lots of time for activities such as Old Orchard Country Club.