The Best Family Hotels in Pittsfield, MA from AED 255 in 2026

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Our top choices for Pittsfield family-friendly hotels

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, desk, laptop workspace, blackout drapes

1. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

Berkshire family fun with free breakfast and ski-area adventures just minutes from winter sports and hiking trails.

AED 404

AED 451 total

includes taxes & fees

15 Sep - 16 Sep

Hypo-allergenic bedding available, desk, laptop workspace

2. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Family adventures await with a heated indoor pool, kid-friendly dining, and spacious suites in the heart of Pittsfield.

AED 422

AED 472 total

includes taxes & fees

12 Oct - 13 Oct

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

Pittsfield

Splash into family fun with indoor pool and hot tub—just minutes from Bousquet Ski Area and Tanglewood Music Center.

AED 477

AED 533 total

includes taxes & fees

13 Oct - 14 Oct

Desk, iron/ironing board, WiFi (free), bed sheets

4. FairBridge Inn Express

Pittsfield

AED 228

AED 255 total

includes taxes & fees

14 Sep - 15 Sep

3 bedrooms, desk, iron/ironing board, WiFi

5. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield

AED 1,098

AED 1,879 total

includes taxes & fees

13 Oct - 14 Oct

6 bedrooms, in-room safe, iron/ironing board, WiFi (free)

Coffee/tea maker, fridge, microwave, oven

6. Hancock Village Inn Near Jiminy Peak

Hancock

AED 2,310

AED 4,220 total

includes taxes & fees

15 Sep - 16 Sep

7. The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

Family fun at lakeside retreat with kayaking, fishing, and premium TV channels.

AED 459

AED 513 total

includes taxes & fees

21 Sep - 22 Sep

8. Element by Marriott Lenox Berkshires

Lenox

AED 654

AED 730 total

includes taxes & fees

20 Sep - 21 Sep

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Choose what matters most at family-friendly hotels in Pittsfield

Pool

Breakfast included

All-inclusive

4 stars

5 stars

Top Pittsfield Hotel Reviews

The Yankee Inn

8/10 Good

"Beautiful views, friendly and responsive staff, property well kept. I would have given the highest praise except the indoor pool was closed for painting and maintenance. When I booked there was no notice in the website or Expedia. Since they had an outdoor pool and it was early fall, we swam theredes"

Quality Inn Great Barrington

10/10 Excellent

"Outstanding customer service from Wylie, delicious food, coffee in lobby always available, superb housekeeping staff, quiet room, wide range of television channels including multiple HBO stations. We’re coming back!"

Hotel Downstreet, an Ascend Collection Hotel

8/10 Good

"Clean room, great location. Perfect base for a weekend in the Berkshires."

Best Western Plus Berkshire Hills Inn & Suites

8/10 Good

"Clean, staff was great, and ample parking"

The Central Downtown Inn & Suites

8/10 Good

"It was priced well. The central location was convenient. The space inside was much larger than usual. There was a bedroom, living room and dining room combo with a full kitchen. It appears that it was an apartment at one time."

Hotel On North

10/10 Excellent

"Best place in town"

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good

"Staff was helpful. Location close to Tanglewood. Bed and pillows were awesome. One elevator was not working so that was inconvenient"

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 Berkshire Athenaeum and Guido's Marketplace.

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.

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Pittsfield Family Hotels

Our top choices for Pittsfield family-friendly hotels

1. Best Western Plus Berkshire Hills Inn & Suites

2. Holiday Inn & Suites Pittsfield-Berkshires by IHG