Search Family-Friendly Hotels in Pittsfield

  • 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

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.
"We have a dog traveling with us. It is really pet friendly. Love it!"
United States
Yan
The price is 2.895.558 ₫
3.234.339 ₫ total
includes taxes & fees
20 May - 21 May
Best Western Plus Berkshire Hills Inn & Suites
Indoor pool

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (96 reviews)
  • cleanliness
    Splash into family fun with indoor pool and hot tub—just minutes from Bousquet Ski Area and Tanglewood Music Centre.
"Room was clean, bed was comfortable, pool was nice, breakfast and coffee were good!"
United States
Haley
The price is 3.346.704 ₫
3.738.295 ₫ total
includes taxes & fees
28 May - 29 May
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Exterior

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, (1,000 reviews)
  • cleanliness
    Family adventures await with a heated indoor pool, kid-friendly dining, and spacious suites in the heart of Pittsfield.
"kids had so much fun"
United States
Kristen
The price is 3.109.536 ₫
3.473.352 ₫ total
includes taxes & fees
25 May - 26 May
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)
"Parking good. Killed two cockroaches "
United States
John
The price is 1.873.627 ₫
2.092.876 ₫ total
includes taxes & fees
31 May - 1 Jun
FairBridge Inn Express
Exterior

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (905 reviews)
"Friendly hotel workers, great breakfast, and my daughter loved the lobby decor. Perfect for a mother-daughter weekend away!"
United States
Janice
The price is 2.087.078 ₫
2.459.695 ₫ total
includes taxes & fees
31 May - 1 Jun
Cozy Corner Motel
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, (579 reviews)
  • cleanliness
    Escape with the kids to this quiet, comfortable motel where family stays come with free beds and cots in immaculately clean rooms.
"Really nice little family business. Ty! "
United States
Raymond
The price is 1.976.400 ₫
2.207.639 ₫ total
includes taxes & fees
19 May - 20 May
Travelodge by Wyndham Great Barrington Berkshires
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, (1,008 reviews)
"After spending time with my family, the pool was very relaxing."
United States
Elizabeth
The price is 3.093.461 ₫
3.433.741 ₫ total
includes taxes & fees
14 Jun - 15 Jun
Comfort Inn & Suites East Greenbush - Albany
Lake

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Family fun at lakeside retreat with kayaking, fishing, and premium TV channels.
"We wojld considrr returning in warmer weather with the kids/ grandkids as the environment is family friendly."
United States
Melody
The price is 3.404.678 ₫
3.803.026 ₫ total
includes taxes & fees
9 Jun - 10 Jun
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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

Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

8/10 Good
"Breakfast area was clean and the food was decent."
Vito 3-night trip
Posted 7 hours ago
Comfort Inn & Suites East Greenbush - Albany

Frequently asked questions

What's Pittsfield like for family-friendly holidays?
The historic destination of Pittsfield is a good choice if you've been thinking about a trip with your children. The cycling trails, entertainment and lake views are just some of the things that make this a good destination for family holidays. 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.
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?
Barrington Stage Company, Bousquet Ski Area and Colonial Theater 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.