Family friendly Hotels, Pittsfield Massachusetts

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

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Check availability on Pittsfield Family friendly Hotels

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Our top choices for Pittsfield family-friendly hotels

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.

P6,924

P7,734 total

includes taxes & fees

Aug 30 - Aug 31

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.

P7,715

P8,618 total

includes taxes & fees

Sep 1 - Sep 2

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.

P7,958

P8,889 total

includes taxes & fees

Sep 10 - Sep 11

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

4. FairBridge Inn Express

Pittsfield

P3,772

P4,214 total

includes taxes & fees

Aug 19 - Aug 20

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

Lee

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

P8,158

P9,113 total

includes taxes & fees

Sep 10 - Sep 11

6. Element by Marriott Lenox Berkshires

Lenox

P12,966

P14,483 total

includes taxes & fees

Aug 23 - Aug 24

Iron/ironing board, cribs (free), WiFi, bed sheets

7. Holiday Inn Club Vacations Oak 'n Spruce Resort

South Lee

P6,506

P8,455 total

includes taxes & fees

Sep 10 - Sep 11

Outdoor pool, open 8:00 AM to 10:00 PM, pool umbrellas, sun loungers

8. Jiminy Peak Mountain Resort

Hancock

Family-friendly mountain resort with pools and skiing thrills for all ages in Jiminy Peak.

P9,659

P10,789 total

includes taxes & fees

Sep 10 - Sep 11

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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

Vacation Village in the Berkshires

10/10 Excellent

"Thus was a quick over night for us but we will be back. There was allt of bang for your buck, outside pool with grills to use plenty for the little people to do, also has an inside pool with a huge hot tub. The room was absolutely amazing. Dont hesitate on booking here, we'll worth it"

The Yankee Inn

8/10 Good

"The room was clean. Linens in good shape. Good access to lots of activities nearby. Breakfast can be crowded. Go early."

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent

"Hotel is currently under renovation which impacted parking and only 1 elevator available. Hotel staff, cleanliness and location excellent."

Comfort Inn & Suites East Greenbush - Albany

8/10 Good

"Great stay. Very easy and affordable. No issues."

Berkshire Inn

8/10 Good

"We were pleased with our stay. Clean and quiet. Nice pool too. Considering the money it was a good value and we would definitely stay there again."

The Central Downtown Inn & Suites

8/10 Good

"This place was well situated for walks downtown. The suite was clean, spacious and well worth the money. Check in was done by phone which was a little different but it all ran smooth. I would do it again in a heartbeat."

Howard Johnson by Wyndham Lenox

10/10 Excellent

"Parking"

FairBridge Inn Express

10/10 Excellent

"Stayed for 2 nights. Room was nice and clean, had shampoo, conditioner, soap, hair dryer. Bed was pretty comfortable. Definitely not bad for the price. Would stay here again."

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 Holiday Inn & Suites Pittsfield-Berkshires by IHG and Best Western Plus Berkshire Hills Inn & Suites.

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.

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Pittsfield Family friendly 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