Pittsfield Hotel Guide - Family Friendly Hotels in Pittsfield, Massachusetts

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Our top choices for Pittsfield family-friendly hotels

1. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (982 reviews)
The price is €116
includes taxes & fees
29 Nov - 30 Nov
Hotel On North

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,266 reviews)
The price is €97
includes taxes & fees
6 Dec - 7 Dec
Berkshire Mountain Lodge

3. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (717 reviews)
The price is €118
includes taxes & fees
15 Nov - 16 Nov
Hilton Garden Inn Lenox Pittsfield

4. 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, (1,002 reviews)
  • cleanliness
    Berkshire family fun with free breakfast and ski-area adventures just minutes from winter sports and hiking trails.
The price is €93
includes taxes & fees
1 Dec - 2 Dec
Best Western Plus Berkshire Hills Inn & Suites

5. 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, (258 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 €110
includes taxes & fees
15 Nov - 16 Nov
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

6. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very good, (436 reviews)
The price is €97
includes taxes & fees
24 Nov - 25 Nov
The Central Downtown Inn & Suites

7. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
7.8 out of 10, Good, (1,001 reviews)
  • cleanliness
    Family adventures await with a heated indoor pool, kid-friendly dining, and spacious suites in the heart of Pittsfield.
The price is €98
includes taxes & fees
11 Dec - 12 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG

8. FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (935 reviews)
The price is €71
includes taxes & fees
11 Nov - 12 Nov
FairBridge Inn Express

9. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
8.6 out of 10, Excellent, (11 reviews)
The price is €425
includes taxes & fees
23 Nov - 24 Nov
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

10. Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (22 reviews)
The price is €975
includes taxes & fees
17 Nov - 18 Nov
Hancock Village Inn Near Jiminy Peak
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.

Choose what matters most at family-friendly hotels in Pittsfield

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.