Find Family Hotels in Pittsfield, MA

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Check availability on Pittsfield Family Hotels

Tonight
Jul 31 - Aug 1
Tomorrow
Aug 1 - Aug 2
This weekend
Aug 1 - Aug 3
Next weekend
Aug 8 - Aug 10

Top Pittsfield Family Hotels

Holiday Inn Express & Suites Pittsfield - Berkshires
Enjoy a diverse selection of hot and cold dishes at our buffet.

Holiday Inn Express & Suites Pittsfield - Berkshires

2.5 star property
10.0 out of 10, Exceptional, (4)
"Our stay was terrific, and we appreciated the staff's attentiveness, especially Anthony's."
The price is ₩246,981
₩275,878 total
includes taxes & fees
Aug 6 - Aug 7
Holiday Inn Express & Suites Pittsfield - Berkshires
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, (1019)
"Very nice stay"
The price is ₩187,895
₩209,879 total
includes taxes & fees
Aug 3 - Aug 4
Best Western Plus Berkshire Hills Inn & Suites
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, (839)
"I like this place a lot and have stayed here many times over the years. Comfortable stay at a reasonable price at a convenient location in Pittsfield. "
The price is ₩179,345
₩200,328 total
includes taxes & fees
Aug 17 - Aug 18
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
6.4 out of 10, (615)
"It was a clean, well-run, low cost option. "
The price is ₩88,605
₩98,971 total
includes taxes & fees
Aug 13 - Aug 14
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, (1000)
"Beautiful location!"
The price is ₩270,616
₩302,278 total
includes taxes & fees
Aug 7 - Aug 8
The Black Swan Lee - Lenox, Ascend Hotel Collection
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Enjoy a fun gaming experience with arcade games like American Idol and Super Star, plus a flat-screen TV for entertainment.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.4 out of 10, Exceptional, (722)
"No complaints at all. Great place to stay!"
The price is ₩209,931
₩234,493 total
includes taxes & fees
Aug 27 - Aug 28
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
7.4 out of 10, Good, (536)
"Run down old property , room smelled , dirty carpet "
The price is ₩137,637
₩153,736 total
includes taxes & fees
Aug 3 - Aug 4
Travelodge by Wyndham Great Barrington Berkshires
Jiminy Peak Mountain Resort
Stunning hotel with a central entrance and multiple balconies, offering a unique perspective on the surrounding landscape.

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (956)
"Everything was convenient and the staff was friendly and helpful, even though we were there in the off season"
The price is ₩248,858
₩277,974 total
includes taxes & fees
Aug 3 - Aug 4
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.

Top Pittsfield Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Loved our visit"
Barbara 1-night trip
Posted 1 day ago
The Red Lion Inn

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?
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 choices for your family trip include Best Western Plus Berkshire Hills Inn & Suites 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.