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Find Family Hotels in Stockbridge, MA

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Top Stockbridge Family Hotels

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
Pittsfield
  • Cribs/infant beds
8.6 out of 10, Excellent, (1000)
Family memories await at this thoughtful property, featuring spacious suites with premium TV channels and blackout drapes for restful evenings. Complimentary breakfast fuels adventures before heading to nearby Bousquet Ski Area, just a quick 5-minute drive away.
The price is AED 343
AED 384 total
includes taxes & fees
20 Nov - 21 Nov
Best Western Plus Berkshire Hills Inn & Suites

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
  • Cribs/infant beds provided
  • Indoor pool
8.0 out of 10, Very Good, (955)
Spacious suites accommodate families with comfort, while children splash in the heated indoor pool year-round. Located steps from Berkshire Museum, this hotel offers complimentary cribs and rollaway beds, alongside a restaurant serving delicious meals for hungry explorers.
The price is AED 324
AED 362 total
includes taxes & fees
21 Nov - 22 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
Lee
  • Cribs/infant beds provided
9.0 out of 10, Wonderful, (1002)
Playtime paradise awaits with free cribs, kayaking on the sparkling lake, and motor boating adventures. Children delight in fishing excursions, premium TV entertainment, and beachside fun while parents appreciate the lakefront setting and complimentary breakfast each morning.
The price is AED 403
AED 450 total
includes taxes & fees
4 Dec - 5 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Element Lenox Berkshires

3.0 star property
Lenox
  • Indoor pool
9.6 out of 10, Exceptional, (10)
The price is AED 496
AED 554 total
includes taxes & fees
20 Nov - 21 Nov
Element Lenox Berkshires

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
Great Barrington
  • Cribs/infant beds provided
7.6 out of 10, Good, (558)
Family vacations shine at this peaceful Berkshire retreat offering complimentary cribs and rollaway beds for little ones. The refreshing pool delights with sunny and shaded areas, while the spotless accommodations and helpful staff ensure carefree comfort for travelers of all ages.
The price is AED 275
AED 308 total
includes taxes & fees
15 Nov - 16 Nov
Travelodge by Wyndham Great Barrington Berkshires

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
  • Cribs/infant beds provided
  • Indoor pool
9.4 out of 10, Exceptional, (58)
Vacation-ready accommodations feature premium TV channels and complimentary cribs for little travelers. Mornings begin with a free breakfast buffet, fueling adventures to nearby attractions. Spotlessly clean facilities and cheerful staff ensure a relaxing family retreat.
The price is AED 403
AED 450 total
includes taxes & fees
11 Dec - 12 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Jiminy Peak Mountain Resort

3.0 star property
Hancock
  • Outdoor pool
8.2 out of 10, Very Good, (984)
Mountain adventures captivate young travelers at this ski-in/ski-out resort with an outdoor pool, tennis courts, and fully equipped kitchens. Families appreciate the quiet atmosphere, friendly staff, and variety of seasonal activities from skiing to biking.
The price is AED 547
AED 611 total
includes taxes & fees
15 Nov - 16 Nov
Jiminy Peak Mountain Resort

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
Great Barrington
  • Cribs/infant beds provided
  • Arcade/game room
9.4 out of 10, Exceptional, (754)
Vibrant game room captivates young adventurers while parents unwind in the soundproof accommodations or hot tub. After complimentary breakfast, families explore nearby skiing or Housatonic River Walk, returning to swim sessions in the pristine indoor pool.
The price is AED 525
AED 587 total
includes taxes & fees
18 Nov - 19 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Prospect Berkshires

3.0 star property
Egremont
  • Outdoor pool
9.4 out of 10, Exceptional, (13)
The price is AED 955
AED 1,190 total
includes taxes & fees
24 Nov - 25 Nov
Prospect Berkshires

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

3.5 star property
South Lee
  • Cribs/infant beds provided
  • 2 outdoor pools
  • Arcade/game room
9.0 out of 10, Wonderful, (781)
The price is AED 468
AED 574 total
includes taxes & fees
16 Nov - 17 Nov
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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, Frelinghuysen Morris House and Studio, and Berkshire Theatre Festival. Make sure you have lots of time for activities like Mission House and Schantz Galleries.