Family friendly Hotels in Pittsfield, Massachusetts

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Check availability on Pittsfield Family friendly Hotels

Top Pittsfield Family friendly Hotels

Lobby sitting area
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1000)
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
United States
Jeanine
The price is P5,515
P6,160 total
includes taxes & fees
Nov 23 - Nov 24
Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (60)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is P6,218
P6,946 total
includes taxes & fees
Dec 14 - Dec 15
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
8.0 out of 10, Very Good, (962)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is P5,198
P5,806 total
includes taxes & fees
Nov 22 - Nov 23
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Desk, iron/ironing board, free WiFi, bed sheets
FairBridge Inn Express

FairBridge Inn Express

2.5 star property
Pittsfield
5.4 out of 10, (810)
"Room spotless and staff helpful."
United States
William
The price is P4,425
P4,943 total
includes taxes & fees
Nov 23 - Nov 24
FairBridge Inn Express
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
United States
joel
The price is P7,728
P8,633 total
includes taxes & fees
Dec 11 - Dec 12
Element Lenox Berkshires
Exterior
Cozy Corner Motel

Cozy Corner Motel

2.0 star property
Williamstown
9.2 out of 10, Wonderful, (882)
"Clean, Great Staff, Quiet"
United States
john
The price is P4,407
P5,202 total
includes taxes & fees
Nov 30 - Dec 1
Cozy Corner Motel
Egyptian cotton sheets, premium bedding, down comforters, minibar
Prospect Berkshires

Prospect Berkshires

3.0 star property
Egremont
9.6 out of 10, Exceptional, (14)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
The price is P15,322
P19,089 total
includes taxes & fees
Dec 21 - Dec 22
Prospect Berkshires
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
Lee
9.0 out of 10, Wonderful, (1000)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is P6,268
P7,002 total
includes taxes & fees
Dec 21 - Dec 22
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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.
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Top Pittsfield Hotel Reviews

Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent
"Would stay there again"
Matthew 1-night trip
Posted 4 days ago
Comfort Inn & Suites East Greenbush - Albany

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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 - 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 Berkshire Athenaeum 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 Barrington Stage Company 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.