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

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

This weekend
6 Nov - 8 Nov
Next weekend
13 Nov - 15 Nov

Our top choices for Pittsfield family-friendly hotels

A bookshelf with various books and games, a 'RELAX' sign, and two red pillows on a bench.

1. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (980 reviews)
"Very nice hotel"
United States
Philip
The price is Rp2.099.320
Rp2.344.941 total
includes taxes & fees
29 Nov - 30 Nov
Hotel On North
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

2. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very good, (434 reviews)
"Consistently, a clean, quiet, convenient location and comfortable stay."
United States
Debra
The price is Rp1.790.118
Rp1.999.508 total
includes taxes & fees
8 Nov - 9 Nov
The Central Downtown Inn & Suites
A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.

3. Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (941 reviews)
"It was an ok place to stay for 2 nights"
United States
cheryl
The price is Rp1.497.007
Rp1.672.157 total
includes taxes & fees
28 Nov - 29 Nov
Berkshire Inn
An indoor swimming pool with clear water, tiled floors, and a blue wall.

4. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (257 reviews)
"The room was clean and well kept, breakfast was amazing!"
United States
Ruth
The price is Rp1.871.304
Rp2.090.248 total
includes taxes & fees
6 Dec - 7 Dec
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A hotel patio with outdoor seating and a fire pit.

5. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (716 reviews)
"Great place to stay. Great staff and convenient location. Nice restaurant as well."
United States
James
The price is Rp2.145.972
Rp2.396.950 total
includes taxes & fees
15 Nov - 16 Nov
Hilton Garden Inn Lenox Pittsfield
A room with a pool table, arcade games, and seating areas.

6. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,257 reviews)
"Comfortable stay, well stocked kitchen and room."
United States
Charline
The price is Rp1.394.485
Rp1.963.512 total
includes taxes & fees
6 Dec - 7 Dec
Berkshire Mountain Lodge
A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

7. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.4 out of 10, Very good, (1,001 reviews)
"Room was spacious and clean"
United States
James
The price is Rp1.690.305
Rp1.888.071 total
includes taxes & fees
1 Dec - 2 Dec
Best Western Plus Berkshire Hills Inn & Suites
A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.

8. FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (934 reviews)
"Friendly staff"
United States
William
The price is Rp1.285.630
Rp1.436.049 total
includes taxes & fees
8 Nov - 9 Nov
FairBridge Inn Express
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 Red Lion Inn

The Red Lion Inn

8/10 Good
"Great location - hotel has an excellent dining room and there are several other restaurants within easy walking distance from hotel. A historic, old hotel with lots of curated artwork and history."
Lisabeth 2-night trip
Posted 16 hours ago
The Red Lion 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, Bousquet Ski Area and Barrington Stage Company 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 Guido's Marketplace and Berkshire Athenaeum.
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.