Family friendly Hotels in Pittsfield, Massachusetts

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Check availability on Pittsfield Family friendly Hotels

Tonight
Oct 4 - Oct 5
Tomorrow
Oct 5 - Oct 6
Next weekend
Oct 10 - Oct 12
In two weeks
Oct 17 - Oct 19

Top Pittsfield Family friendly Hotels

Element Lenox Berkshires
Exterior

Element Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (5)
"New hotel very nice"
The price is P8,796
P9,825 total
includes taxes & fees
Nov 2 - Nov 3
Element Lenox Berkshires
Prospect Berkshires
Egyptian cotton sheets, premium bedding, down comforters, minibar

Prospect Berkshires

3.0 star property
9.0 out of 10, Wonderful, (7)
"Gorgeous thoughtfully designed cabins with so many amenities/activities. Cliff house restaurant was delicious. Perfect getaway. "
The price is P16,927
P20,847 total
includes taxes & fees
Nov 2 - Nov 3
Prospect Berkshires
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
9.0 out of 10, Wonderful, (1003)
"Great Indian restaurant in the hotel!"
The price is P6,149
P6,868 total
includes taxes & fees
Nov 2 - Nov 3
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (889)
"Excellent customer service and great rooms"
The price is P5,961
P6,658 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1000)
"Great property would certainly stay again."
The price is P5,884
P6,573 total
includes taxes & fees
Nov 2 - Nov 3
Best Western Plus Berkshire Hills Inn & Suites
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Lobby sitting area

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.4 out of 10, Exceptional, (49)
"Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout"
The price is P8,313
P9,286 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Berkshire Inn
Property grounds

Berkshire Inn

2.0 star property
7.8 out of 10, Good, (825)
"The bed was very comfortable."
The price is P4,629
P5,171 total
includes taxes & fees
Nov 2 - Nov 3
Berkshire Inn
FairBridge Inn Express
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

2.5 star property
5.4 out of 10, (785)
"Good service and people"
The price is P4,635
P5,178 total
includes taxes & fees
Oct 18 - Oct 19
FairBridge Inn Express
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.
View all properties

Top Pittsfield Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Great place! Food excellent ss well!"
Crystal 1-night trip
Posted 4 days ago
The Red Lion Inn

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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, 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.