Pittsfield Family Friendly Hotels, Massachusetts: Pittsfield Hotel Guide

Check availability on Pittsfield Family Friendly Hotels

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Our top choices for Pittsfield family-friendly hotels

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)

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.

includes taxes & fees

28 May - 29 May

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.

includes taxes & fees

1 Jun - 2 Jun

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

Pittsfield

includes taxes & fees

27 May - 28 May

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

Hancock Village Inn Near Jiminy Peak

Hancock

includes taxes & fees

2 Jun - 3 Jun

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

FairBridge Inn Express

Pittsfield

includes taxes & fees

7 Jun - 8 Jun

Comfort Inn & Suites East Greenbush - Albany

Castleton-on-Hudson

includes taxes & fees

28 May - 29 May

Cozy Corner Motel

Williamstown

includes taxes & fees

31 May - 1 Jun

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

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

includes taxes & fees

28 May - 29 May

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Choose what matters most at family-friendly hotels in Pittsfield

Pool

Breakfast included

Top Pittsfield Hotel Reviews

Vacation Village in the Berkshires

10/10 Excellent

"The room was great. Had a kitchen, huge jetted tub, and private bedroom. Great area! I don't like paying resort fees for things we don't use though. It was raining and we arrived late at night. The indoor pool was amazingly crowded for 10pm. Must have been at least 25 people, including younger children. Earlier check out, 10 am, compared to usual 11:00 other places."

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent

"The check in process was quick and easy. The room was clean except the sofa bed had several stains and I could not trust my kid sleeping on it even with sheets covering it. Other than that the room was clean. the water pressure and temperature of the shower was great. The beds were comfortable and the staff was helpful. I would stay here again if I am in the area."

The Yankee Inn

10/10 Excellent

"Had a great stay at the Yankee Inn. I would definitely stay here again. Check in was great and super helpful for what to do and eat in the area. Carl at the bar was the best! Only complaint is that the fitted sheet kept coming up from our king mattress I had the fix them multiple times. Nice indoor pool and hot tub. Close to a lot."

Berkshire Inn

2/10 Terrible

"blood stains there were blood stains on the carpet and poop stains or some form of weird stains on the carpet room smelled really weird. It was making my nose run water. The atmosphere felt very creaky and disgusting. The staff was not helpful nor they’re caring about my situation. I end up not staying at the property. I end up returning the key asking for a refund and they told me no however I could not stay on site. I had to leave if there’s any way for me to get my money back I’d really appreciate it because it was not sanitary for me to stay in that room and it was genuinely affecting my health. My throat started to itch my nose and my eyes are running water and there were blood stains all over the carpet. Disgusting this place should be shut down."

The Red Lion Inn

10/10 Excellent

"Every year my sisters and I go to the Red Lion to celebrate our mom’s birthday. It was one of her favorite places! We love the charm, the history and the “old fashioned” feel. Every guest room is different and they kindly upgraded me to a suite the last two times. The food at the restaurant is really good and we always love hearing the Jazz in the Lion’s Den on Sunday night. Can’t wait to return next year."

Frequently asked questions

What's Pittsfield like for family-friendly holidays?

The historic destination of Pittsfield is a good choice if you've been thinking about a trip with your children. The cycling trails, entertainment and lake views are just some of the things that make this a good destination for family holidays. 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 & Suites Pittsfield-Berkshires by IHG is a hotel with an indoor pool and a restaurant, and it's a top choice on Expedia for families. Other good options for your family trip include Holiday Inn Express & Suites Pittsfield - Berkshires by IHG and Best Western Plus Berkshire Hills Inn & Suites.

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?

Barrington Stage Company, Bousquet Ski Area and Colonial Theater 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 Berkshire Athenaeum and Crane Museum of Papermaking.

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.

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Check availability on Pittsfield Family Friendly Hotels

Our top choices for Pittsfield family-friendly hotels

Best Western Plus Berkshire Hills Inn & Suites

Holiday Inn & Suites Pittsfield-Berkshires by IHG