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Our top choices for Stockbridge family-friendly hotels

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, (33 reviews)
"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "
United States
cathy c.
The price is AED 1,098
AED 2,388 total
includes taxes & fees
27 Jan - 28 Jan
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

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, (1,005 reviews)
"Very friendly and good Breakfast."
United States
Jesse
The price is AED 346
AED 387 total
includes taxes & fees
28 Jan - 29 Jan
Best Western Plus Berkshire Hills Inn & Suites

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (18 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is AED 511
AED 570 total
includes taxes & fees
1 Feb - 2 Feb
Element Lenox 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, (1,002 reviews)
"Staff was very courteous and rooms clean."
United States
Steven
The price is AED 360
AED 402 total
includes taxes & fees
30 Jan - 31 Jan
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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, (1,001 reviews)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is AED 372
AED 415 total
includes taxes & fees
5 Feb - 6 Feb
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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, (765 reviews)
"Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again."
United States
Dinh
The price is AED 555
AED 620 total
includes taxes & fees
1 Feb - 2 Feb
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (567 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is AED 275
AED 308 total
includes taxes & fees
27 Jan - 28 Jan
Travelodge by Wyndham Great Barrington Berkshires

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, (825 reviews)
"Great overnights stay, wish I was here longer "
United States
Thomas
The price is AED 443
AED 567 total
includes taxes & fees
28 Jan - 29 Jan
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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, (79 reviews)
"it was a lovely hotel, hot tub was perfect after the day of skiing, everything very clean and new and lovely breakfast. All staff were very nice."
United States
Laura Pearson
The price is AED 468
AED 522 total
includes taxes & fees
29 Jan - 30 Jan
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (19 reviews)
"Excellent local stay - would recommend to all"
United States
Gentian
The price is AED 632
AED 829 total
includes taxes & fees
27 Jan - 28 Jan
Prospect 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.

Top Stockbridge Hotel Reviews

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