A nighttime view of a residential area with houses adorned with holiday lights.

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Our top choices for Stockbridge family-friendly hotels

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, (1,003 reviews)
  • cleanliness
    Berkshire family fun with free breakfast and ski-area adventures just minutes from winter sports and hiking trails.
The price is NT$4,311
NT$4,816 total
includes taxes & fees
Jul 5 - Jul 6
Best Western Plus Berkshire Hills Inn & Suites

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (118 reviews)
  • cleanliness
    Splash into family fun with indoor pool and hot tub—just minutes from Bousquet Ski Area and Tanglewood Music Center.
The price is NT$5,453
NT$6,091 total
includes taxes & fees
Jul 6 - Jul 7
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (28 reviews)
The price is NT$6,473
NT$7,230 total
includes taxes & fees
Jul 19 - Jul 20
Element by Marriott Lenox Berkshires

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,003 reviews)
  • cleanliness
    Family fun at lakeside retreat with kayaking, fishing, and premium TV channels.
The price is NT$5,150
NT$5,752 total
includes taxes & fees
Jul 6 - Jul 7
The Black Swan Lee - Lenox, an Ascend Collection Hotel

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (837 reviews)
The price is NT$1,980
NT$2,212 total
includes taxes & fees
Jul 16 - Jul 17
FairBridge Inn Express

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.4 out of 10, Good, (589 reviews)
  • cleanliness
    Escape with the kids to this quiet, comfortable motel where family stays come with free beds and cribs in immaculately clean rooms.
The price is NT$2,838
NT$3,170 total
includes taxes & fees
Jul 5 - Jul 6
Travelodge by Wyndham Great Barrington Berkshires

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, (1,000 reviews)
  • cleanliness
    Family adventures await with a heated indoor pool, kid-friendly dining, and spacious suites in the heart of Pittsfield.
The price is NT$5,134
NT$5,735 total
includes taxes & fees
Jul 12 - Jul 13
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.2 out of 10, Wonderful, (921 reviews)
The price is NT$5,223
NT$6,458 total
includes taxes & fees
Jul 7 - Jul 8
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (671 reviews)
  • cleanliness
    Family-friendly budget escape with free miniature golf and breakfast, minutes from Berkshire Botanical Garden.
The price is NT$2,809
NT$3,138 total
includes taxes & fees
Jul 13 - Jul 14
Econo Lodge Lee - Great Barrington
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.

Choose what matters most at family-friendly hotels in Stockbridge

Top Stockbridge Hotel Reviews

Frequently asked questions

What's Stockbridge like for family-friendly vacations?
The historic destination of Stockbridge is a great choice if you've been considering a vacation with the kids. The camping sites, museums, and interesting architecture are just a few things that make this an attractive place for families. 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 20 mi (32.3 km) from the city center.
When's the best time to book a family-friendly vacation in Stockbridge?
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 Stockbridge 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 Stockbridge?
While you are visiting Stockbridge, you might want to round up the kiddos and make time to see interesting attractions such as Naumkeag Museum, Mission House, and Berkshire Theatre Festival. Make sure you have lots of time for activities like Schantz Galleries and Frelinghuysen Morris House and Studio.

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