Book Kid-Friendly Hotels in Stockbridge from $257

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Top Stockbridge Kid Friendly Hotels

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

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

26 Glendale Road, RR 183 Stockbridge MA
$358 nightly
The price is $399 total per night from Aug 10 to Aug 11
$399 total
Aug 10 - Aug 11
Total with taxes and fees
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this bed & breakfast. Guests will appreciate free perks like continental breakfast ...
9.2/10 Wonderful! (113 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."

Reviewed on Jul 14, 2026

Opens in a new windowThe Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Red Lion Inn

The Red Lion Inn

30 Main Street Stockbridge MA
$230 nightly
The price is $257 total per night from Jul 29 to Jul 30
$257 total
Jul 29 - Jul 30
Total with taxes and fees
This historic hotel includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in ...
8.8/10 Excellent! (1,010 reviews)
"I love the Red Lion Inn because of its Old World charm. My husband thinks it could use some new rugs and fix cracked ceiling, but that does not bother me in the least. I just enjoy the place, including the dining room. Our room was very large and comfortable and very clean---no complaints at all. ..."

Reviewed on Jul 27, 2026

Opens in a new windowThe Red Lion Inn
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.

Hotels With Pools in Stockbridge

Hotels with Childcare in Stockbridge

The Red Lion Inn

The Red Lion Inn

30 Main Street Stockbridge MA
$230 nightly
The price is $257 total per night from Jul 29 to Jul 30
$257 total
Jul 29 - Jul 30
Total with taxes and fees
8.8/10 Excellent! (1,010 reviews)

Stockbridge Kid-Friendly Hotels

It’s not a family vacation if you can’t bring the entire clan with you, is it? Next time you have a few days off from work, plan a family-friendly getaway.  Set off on an adventure the entire family will love, and book your stay at one of the kid-friendly hotels in Stockbridge.

Your little ones are the most important thing in your life, so make sure they enjoy your accommodation as much as you do. From a kids-only room service menu (macaroni and cheese, anyone?) to special perks like in-room video game consoles, these lodgings provide a little something extra for the smaller members of your crew. The best family-friendly hotels in Stockbridge may even offer playgrounds and other activities to keep the kiddos busy. What’s more, some hotels provide a babysitting service so you can get a few hours to yourself!

Whether you’re traveling with one small child or hauling around your entire extended family, Travelocity is here to help. Let us hook you up with hotels for kids in Stockbridge that will keep your youngsters happy without breaking the bank. You can save even more when you bundle your flight and hotel together, so what are you waiting for? Grab your family and get ready to explore!

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