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Find kid-friendly hotels & resorts in Stockbridge, MA from $84

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Check availability on Stockbridge Family Hotels

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Dec 4 - Dec 5
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Dec 5 - Dec 6
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Dec 5 - Dec 7
Next weekend
Dec 12 - Dec 14

Top Stockbridge Family Hotels

Property grounds
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Stockbridge
10.0 out of 10, Exceptional, (29)
"Great stay in a well appointed house close to trails, Stockbridge center, and a quick car trip to Lenox, Great Barrington, Tanglewood, Jacobs Pillow, and Shakespeare & Co. we enjoyed the morning walks, coffee at the Lost Lamb, drinks at the Red Lion Inn, dance at Jacob’s Pillow, music at Tanglewood, ice cream at High Lawn Farm, and just that Berkshire vibe! "
United States
Phillip F.
$764 nightly
The price is $853
Dec 6 - Dec 7
Total with taxes and fees
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Lobby sitting area
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, (1005)
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
United States
Jeanine
$93 nightly
The price is $104
Dec 7 - Dec 8
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
United States
joel
$131 nightly
The price is $146
Dec 11 - Dec 12
Total with taxes and fees
Element Lenox Berkshires
Restaurant
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, (978)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
$92 nightly
The price is $103
Dec 12 - Dec 13
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (64)
"Very clean room, courteous staff. "
United States
Jeffrey
$91 nightly
The price is $102
Dec 14 - Dec 15
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
Lee
9.0 out of 10, Wonderful, (1002)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
$101 nightly
The price is $113
Dec 14 - Dec 15
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Arcade
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
9.0 out of 10, Wonderful, (794)
"Place was great!"
United States
Benjamin
$124 nightly
The price is $139
Dec 8 - Dec 9
Total with taxes and fees
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
In-room safe, desk, free cribs/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
Great Barrington
7.6 out of 10, Good, (562)
"The staff were very friendly and accommodating "
United States
Tom
$75 nightly
The price is $84
Dec 7 - Dec 8
Total with taxes and fees
Travelodge by Wyndham Great Barrington Berkshires
Egyptian cotton sheets, premium bedding, down comforters, minibar
Prospect Berkshires

Prospect Berkshires

3.0 star property
Egremont
9.6 out of 10, Exceptional, (15)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
$247 nightly
The price is $276
Jan 4 - Jan 5, 2026
Total with taxes and fees
Prospect Berkshires
Property amenity
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
Great Barrington
9.4 out of 10, Exceptional, (757)
"Clean room, very courteous staff "
United States
Thomas
$151 nightly
The price is $169
Dec 9 - Dec 10
Total with taxes and fees
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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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Find out more about Stockbridge

Family friendly things to do in Stockbridge

Stockbridge, Massachusetts, offers a delightful blend of family-friendly activities perfect for adventurous travelers. The Norman Rockwell Museum invites families to explore the life and works of America's beloved illustrator, with interactive exhibits that engage children and adults alike. Just a short drive away, the Berkshire Botanical Garden provides a stunning outdoor space where kids can roam and discover a variety of plant species, while parents enjoy the serene landscape. For some fun in the great outdoors, head to Stockbridge Bowl, a beautiful lake ideal for swimming, kayaking, and picnicking—perfect for a family day out. The nearby Tanglewood Music Center often hosts family concerts, introducing children to the magic of live music in a scenic setting. When it comes to accommodations, the Stockbridge area boasts charming family-friendly hotels that prioritize comfort and convenience, ensuring you enjoy spacious rooms and attentive service. Staying near the town center allows for easy access to local dining and shops, making it simple to explore the vibrant community while creating lasting memories with your loved ones.

Find the best family friendly hotels in Stockbridge

Travelers seeking a family-friendly getaway in Stockbridge, Massachusetts will find these hotels ideal for creating lasting memories. Each offers amenities designed for comfort and convenience for all ages.

The Red Lion Inn

  • Why it's great for a family-friendly adventure: The Red Lion Inn is a charming retreat perfect for families, featuring a strong guest review rating of 9.0. With connecting rooms available, it ensures that families can stay close together while enjoying the comfort of home. The daily housekeeping service allows parents to relax, knowing their space is taken care of while they explore the beautiful surroundings of Stockbridge.
  • Other amenities: Guests can unwind in the outdoor pool, perfect for family fun during warm days. The inn also features a lovely garden, ideal for children to play and explore. Additional thoughtful amenities include free cribs for infants, Frette Italian sheets for a touch of luxury, and a historic ambiance that enriches the experience. Nearby activities such as snow tubing and hiking provide ample opportunities for adventure, ensuring families have plenty of options for outdoor enjoyment.
  • Nearby attractions: Housatonic River - 0.13 miles, Berkshire Theatre Festival - 0.51 miles, Naumkeag Museum - 0.64 miles

Top Stockbridge Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"All of the above "
Lois 1-night trip
Posted 1 day ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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, Frelinghuysen Morris House and Studio, and Mission House. Make sure you have lots of time for activities like Schantz Galleries and Berkshire Theatre Festival.

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