The Best Family Hotels in Stockbridge, MA from NT$2,212 in 2026

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check availability on Stockbridge Family Hotels

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Stockbridge family-friendly hotels

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk

Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

Berkshire family fun with free breakfast and ski-area adventures just minutes from winter sports and hiking trails.

NT$4,816 total

includes taxes & fees

Jul 5 - Jul 6

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

Pittsfield

Splash into family fun with indoor pool and hot tub—just minutes from Bousquet Ski Area and Tanglewood Music Center.

NT$6,091 total

includes taxes & fees

Jul 6 - Jul 7

Element by Marriott Lenox Berkshires

Lenox

NT$7,230 total

includes taxes & fees

Jul 19 - Jul 20

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

Family fun at lakeside retreat with kayaking, fishing, and premium TV channels.

NT$5,752 total

includes taxes & fees

Jul 6 - Jul 7

Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

Pittsfield

NT$2,212 total

includes taxes & fees

Jul 16 - Jul 17

In-room safe, desk, free cribs/infant beds, free rollaway beds

Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Escape with the kids to this quiet, comfortable motel where family stays come with free beds and cribs in immaculately clean rooms.

NT$3,170 total

includes taxes & fees

Jul 5 - Jul 6

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Family adventures await with a heated indoor pool, kid-friendly dining, and spacious suites in the heart of Pittsfield.

NT$5,735 total

includes taxes & fees

Jul 12 - Jul 13

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

South Lee

NT$6,458 total

includes taxes & fees

Jul 7 - Jul 8

View all properties

Choose what matters most at family-friendly hotels in Stockbridge

Breakfast included

Pool

Top Stockbridge Hotel Reviews

Quality Inn Lee - Lenox South

10/10 Excellent

"A great budget stay in Berkshires. "

The Yankee Inn

10/10 Excellent

"The Yankee Inn was a convenient and affordable option for our visit to Tanglewood. The check-in staff was friendly and advised us of breakfast and checkout hours. The room was clean and thankfully well air conditioned during our stay there in 90 degree weather! The included breakfast was typical fare: eggs, cereal, yogurt, fresh fruit, bread/pastries, etc. As we were there for only one night, we did not take advantage of the outdoor pool or fire pit, but both appeared to be clean and well maintained."

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

10/10 Excellent

"Our stay at The Inn was wonderful. Diane and staff could not have been more welcoming or helpful with great suggestions. Shopping and picnic supplies were spot on! Breakfast was delicious and more than plentiful. The pool was not available at this time, but what a beautiful setting. We’ll stay here again on our next trip to the Berkshires."

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.

Explore a world of travel with Expedia

Book Family Hotels in Stockbridge on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Stockbridge Family Hotels

Our top choices for Stockbridge family-friendly hotels

Best Western Plus Berkshire Hills Inn & Suites