Find Family Hotels in Stockbridge, MA

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Pick from 3 Stockbridge Family Hotels and compare room rates, reviews, and availability. Most hotels are fully refundable.

The Red Lion Inn
Front of property

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1000)
"The feel of an old fashioned Christmas feel"
The price is AED 757
AED 1,009 total
includes taxes & fees
19 Dec - 20 Dec
The Red Lion Inn
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
View from room

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

4.5 star property
9.2 out of 10, Wonderful, (105)
"The breakfast was one of the best I have ever had. They were fast and lots of choices. It had lots of baked goods. I got the chesdar omeltte and bacon and toast plus fruits in season lime melon etc. Its a lovely place it takes you back in time. The owner is very easy going and nuce and can answer most questions"
The price is AED 1,559
AED 1,885 total
includes taxes & fees
1 Jan - 2 January 2025
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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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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.
How many hotels that welcome families will I find in Stockbridge?
Expedia has 11 family-friendly hotels and other accommodations in Stockbridge.
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 Frelinghuysen Morris House and Studio and Schantz Galleries.