Find Family Hotels in Pittsfield, MA

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Check availability on Pittsfield Family Hotels

Top Pittsfield Family Hotels

Best Western Plus Berkshire Hills Inn & Suites
Welcome to our reception area, featuring a comfortable seating area, a reception desk, and a beautiful abstract art piece.

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1012)
"We have a dog traveling with us. It is really pet friendly. Love it!"
Yan
The price is ₩174,417
₩194,823 total
includes taxes & fees
Jul 27 - Jul 28
Best Western Plus Berkshire Hills Inn & Suites
Holiday Inn Express & Suites Pittsfield - Berkshires
Enjoy a delicious spread of options at our buffet, featuring turkey sausage, bacon, and sweet treats.

Holiday Inn Express & Suites Pittsfield - Berkshires

2.5 star property
10.0 out of 10, Exceptional, (3)
"The staff were all so friendly and helpful and the room and the hotel itself were very nice. Great location. Nice and clean, lovely pool, awesome coffee and a good breakfast. We will absolutely be back again next year to stay here. "
Jeannette
The price is ₩209,535
₩234,051 total
includes taxes & fees
Jul 17 - Jul 18
Holiday Inn Express & Suites Pittsfield - Berkshires
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Dine in style with a long table set for a memorable meal, surrounded by cushioned chairs and large windows offering a view of the outdoors.

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (821)
"Stayed here for the weekend with my
family
it was clean , pool was fun breakfast was good . Only thing was the no parking. We had to park a block down and that walk back to the hotel in the cold was not fun . "
Bryant
The price is ₩158,373
₩176,902 total
includes taxes & fees
Jul 30 - Jul 31
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Econo Lodge Lee - Great Barrington
Relax in comfort with a large bed, two bedside tables, and a balcony with a view.

Econo Lodge Lee - Great Barrington

2.0 star property
6.2 out of 10, (608)
"While the gentleman at the front desk can be a bit cold, the women that work at the property are very pleasant. They were super accommodating and did a nice job cleaning the room during our stay. The room was a good value and provided a nice place for our
family
of 5 plus a small dog to lay our heads at night."
Danny
The price is ₩87,794
₩98,066 total
includes taxes & fees
Aug 3 - Aug 4
Econo Lodge Lee - Great Barrington
The Black Swan Lee - Lenox, Ascend Hotel Collection
Relax in a serene lakeside setting with Adirondack chairs and a tranquil atmosphere.

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1003)
"Lovely view, convenient location."
Thalia
The price is ₩246,512
₩275,353 total
includes taxes & fees
Jul 15 - Jul 16
The Black Swan Lee - Lenox, Ascend Hotel Collection
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Relax in a welcoming space with comfortable seating and a stunning chandelier.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.4 out of 10, Exceptional, (714)
"Staff are so friendly "
Mary Cay
The price is ₩285,072
₩318,426 total
includes taxes & fees
Jul 17 - Jul 18
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Travelodge by Wyndham Great Barrington Berkshires
Relax in this inviting room with a large bed, flat-screen TV, and comfortable chair.

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
7.6 out of 10, Good, (532)
"Really nice little
family
business. Ty! "
Raymond
The price is ₩136,339
₩152,287 total
includes taxes & fees
Jul 17 - Jul 18
Travelodge by Wyndham Great Barrington Berkshires
Jiminy Peak Mountain Resort
Set amidst lush greenery, this hotel complex offers a serene escape with pathways connecting its various buildings.

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (947)
"Awesome place to vacation with
family
! Pool was a little small and not the cleanest. "
Nicole
The price is ₩221,860
₩247,819 total
includes taxes & fees
Jul 28 - Jul 29
Jiminy Peak Mountain Resort
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.

Frequently asked questions

What's Pittsfield like for family-friendly vacations?
The historic destination of Pittsfield is a good choice if you've been thinking about a trip with your kids. The biking trails, entertainment, and lake views are just some of the things that make this a good place for family vacations. 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?
Best Western Plus Berkshire Hills Inn & Suites is a hotel with free parking and free breakfast, 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 Holiday Inn Express & Suites Pittsfield - Berkshires.
How many hotels that welcome families should I expect to find in Pittsfield?
Expedia has 8 family-friendly hotels and other accommodations in Pittsfield.
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, Barrington Stage Company, and Bousquet Ski Area 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 Crane Museum of Papermaking.
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.