Family friendly Hotels in Pittsfield, Massachusetts

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Check prices for these dates

Tonight
Nov 12 - Nov 13
Tomorrow
Nov 13 - Nov 14
This weekend
Nov 13 - Nov 15
Next weekend
Nov 20 - Nov 22

Our top choices for Pittsfield family-friendly hotels

A restaurant with multiple dining tables, chairs, and a large Buddha statue centerpiece.

1. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (718 reviews)
The price is P7,507
P8,385 total
includes taxes & fees
Nov 15 - Nov 16
Hilton Garden Inn Lenox Pittsfield
A bookshelf with various books and games, a 'RELAX' sign, and two red pillows on a bench.

2. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (984 reviews)
The price is P7,344
P8,203 total
includes taxes & fees
Nov 29 - Nov 30
Hotel On North
An indoor swimming pool with clear water, tiled floors, and a blue wall.

3. 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 Center.
The price is P6,484
P7,242 total
includes taxes & fees
Dec 13 - Dec 14
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A reception area with a wooden reception desk, a seating area with sofas, a colorful stained glass window, a mounted television, and various potted plants.

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, (1,003 reviews)
  • cleanliness
    Berkshire family fun with free breakfast and ski-area adventures just minutes from winter sports and hiking trails.
The price is P5,913
P6,605 total
includes taxes & fees
Dec 1 - Dec 2
Best Western Plus Berkshire Hills Inn & Suites
A room with a pool table, arcade games, and seating areas.

5. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,269 reviews)
The price is P4,832
P6,803 total
includes taxes & fees
Dec 6 - Dec 7
Berkshire Mountain Lodge
A large indoor swimming pool with multiple levels of balconies, surrounded by tables and chairs.

6. 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, (1,000 reviews)
  • cleanliness
    Family adventures await with a heated indoor pool, kid-friendly dining, and spacious suites in the heart of Pittsfield.
The price is P6,199
P6,924 total
includes taxes & fees
Dec 11 - Dec 12
Holiday Inn & Suites Pittsfield-Berkshires by IHG
A covered porch with a wooden floor and white railing, overlooking a green lawn and a clear blue sky.

7. 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 P6,121
P6,837 total
includes taxes & fees
Nov 17 - Nov 18
The Central Downtown Inn & Suites
A hotel room with a large bed, a separate bathroom with a bathtub, a large mirror, and a painting on the wall.

8. FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (936 reviews)
The price is P4,476
P4,999 total
includes taxes & fees
Nov 19 - Nov 20
FairBridge Inn Express
Two Adirondack chairs facing a river with a forested hill in the background.

9. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Family escape with indoor and outdoor pools—enjoy year-round swimming plus convenient ski access at Bousquet Ski Area.
The price is P7,931
P8,859 total
includes taxes & fees
Dec 12 - Dec 13
The Yankee Inn
A rectangular swimming pool with a white metal fence, surrounded by white lounge chairs and a blue umbrella.

10. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (937 reviews)
  • cleanliness
    Family escape with outdoor pool and ski resort access—kids love the convenient location and amenities for all ages.
The price is P4,973
P5,555 total
includes taxes & fees
Nov 21 - Nov 22
Howard Johnson by Wyndham Lenox
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.
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Choose what matters most at family-friendly hotels in Pittsfield

Pool
Breakfast included

Frequently Asked Questions

What's Pittsfield like for family-friendly vacations?

If you've been thinking about a trip with your kids, the historic destination of Pittsfield is a good choice. The biking 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 center.

What's the best hotel when traveling with kids to 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 choices 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 vacation in Pittsfield?

The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Pittsfield are January, March, February, and November, with each month seeing an average of 7 inches 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 you and your family will enjoy exploring while you are staying in Pittsfield. Make sure you have lots of time for activities like Guido's Marketplace and Berkshire Athenaeum.

What's the best way for us to get around Pittsfield?

To see more of the surrounding area, ride one of the trains from Pittsfield Intermodal Transportation Center or Pittsfield Station. Pittsfield might not have many public transit options so consider renting a car to explore more.