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Check availability on Stockbridge Family-Friendly Hotels

Top Stockbridge Family-Friendly Hotels

Lobby sitting area
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
Pittsfield
  • Cots/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 1.970.558 ₫
2.201.112 ₫ total
includes taxes & fees
18 Nov - 19 Nov
Best Western Plus Berkshire Hills Inn & Suites
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
  • Cots/infant beds provided
  • Indoor pool
8.0 out of 10, Very good, (958)
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 cots and rollaway beds, alongside a restaurant serving delicious meals for hungry explorers.
The price is 2.324.070 ₫
2.596.002 ₫ total
includes taxes & fees
21 Nov - 22 Nov
Holiday Inn & 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
  • Cots/infant beds provided
9.0 out of 10, Wonderful, (1002)
Playtime paradise awaits with free cots, 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 2.889.278 ₫
3.227.324 ₫ total
includes taxes & fees
7 Dec - 8 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
  • Indoor pool
9.6 out of 10, Exceptional, (10)
The price is 3.557.250 ₫
3.973.449 ₫ total
includes taxes & fees
23 Nov - 24 Nov
Element Lenox Berkshires
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
  • Cots/infant beds provided
  • Indoor pool
9.4 out of 10, Exceptional, (59)
Vacation-ready accommodation feature premium TV channels and complimentary cots for little travellers. Mornings begin with a free breakfast buffet, fuelling adventures to nearby attractions. Spotlessly clean facilities and cheerful staff ensure a relaxing family retreat.
The price is 2.777.290 ₫
3.102.234 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
In-room safe, desk, free cots/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
Great Barrington
  • Cots/infant beds provided
7.6 out of 10, Good, (558)
Family holidays shine at this peaceful Berkshire retreat offering complimentary cots and rollaway beds for little ones. The refreshing pool delights with sunny and shaded areas, while the spotless accommodation and helpful staff ensure carefree comfort for travellers of all ages.
The price is 1.976.250 ₫
2.207.603 ₫ total
includes taxes & fees
17 Nov - 18 Nov
Travelodge by Wyndham Great Barrington Berkshires
Lobby
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
Great Barrington
  • Cots/infant beds provided
  • Arcade/games room
9.4 out of 10, Exceptional, (754)
Vibrant game room captivates young adventurers while parents unwind in the soundproof accommodation 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 3.768.050 ₫
4.208.911 ₫ total
includes taxes & fees
20 Nov - 21 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Egyptian cotton sheets, premium bedding, down duvets, minibar
Prospect Berkshires

Prospect Berkshires

3.0 star property
Egremont
  • Outdoor pool
9.4 out of 10, Exceptional, (13)
The price is 6.851.000 ₫
8.535.555 ₫ total
includes taxes & fees
24 Nov - 25 Nov
Prospect Berkshires
Property amenity
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
  • Cots/infant beds provided
  • 2 outdoor pools
  • Arcade/games room
9.0 out of 10, Wonderful, (782)
The price is 3.530.900 ₫
4.311.861 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Exterior
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3.0 star property
Hancock
  • Outdoor pool
8.2 out of 10, Very good, (985)
Mountain adventures captivate young travellers 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 3.926.150 ₫
4.385.509 ₫ total
includes taxes & fees
17 Nov - 18 Nov
Jiminy Peak Mountain Resort
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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Top Stockbridge Hotel Reviews

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Frequently asked questions

What's Stockbridge like for family-friendly holidays?
The historic destination of Stockbridge is a great choice if you've been considering a holiday with the children. The campsites, 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 centre.
When's the best time to book a family-friendly holiday in Stockbridge?
The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Stockbridge are January, March, February and November, with each month seeing an average of 18 cm of snowfall.
What's there to see and do with your family in Stockbridge?
While you are visiting Stockbridge, you may want to round up the youngsters and make time to see interesting attractions such as Naumkeag Museum, Frelinghuysen Morris House and Studio and Berkshire Theatre Festival. Make sure that you have lots of time for activities such as Mission House and Schantz Galleries.