Family friendly Hotels in The Berkshires, Massachusetts

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Our top choices for The Berkshires family-friendly hotels

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, (1,000 reviews)
  • cleanliness
    Family fun at lakeside retreat with kayaking, fishing, and premium TV channels.
The price is P7,011
P7,831 total
includes taxes & fees
May 5 - May 6
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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, (886 reviews)
The price is P7,832
P9,947 total
includes taxes & fees
May 4 - May 5
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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, (1,001 reviews)
  • cleanliness
    Berkshire family fun with free breakfast and ski-area adventures just minutes from winter sports and hiking trails.
The price is P6,483
P7,241 total
includes taxes & fees
May 3 - May 4
Best Western Plus Berkshire Hills Inn & Suites

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (902 reviews)
The price is P4,854
P5,720 total
includes taxes & fees
May 3 - May 4
Cozy Corner Motel

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
Great Barrington
9.4 out of 10, Exceptional, (778 reviews)
  • cleanliness
    Families splash into fun at this Berkshires hotel with indoor pool, game arcade, and cozy rooms—all nestled near Ski Butternut.
The price is P9,315
P10,405 total
includes taxes & fees
May 6 - May 7
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

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, (91 reviews)
  • cleanliness
    Splash into family fun with indoor pool and hot tub—just minutes from Bousquet Ski Area and Tanglewood Music Center.
The price is P7,783
P8,694 total
includes taxes & fees
May 4 - May 5
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

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, (1,000 reviews)
  • cleanliness
    Family adventures await with a heated indoor pool, kid-friendly dining, and spacious suites in the heart of Pittsfield.
The price is P7,232
P8,078 total
includes taxes & fees
May 17 - May 18
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (577 reviews)
  • cleanliness
    Escape with the kids to this quiet, comfortable motel where family stays come with free beds and cribs in immaculately clean rooms.
The price is P4,596
P5,134 total
includes taxes & fees
Apr 30 - May 1
Travelodge by Wyndham Great Barrington Berkshires

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
3.0 star property
Hancock
8.2 out of 10, Very Good, (990 reviews)
  • cleanliness
    Family-friendly mountain resort with pools and skiing thrills for all ages in Jiminy Peak.
The price is P8,218
P9,180 total
includes taxes & fees
May 1 - May 2
Jiminy Peak Mountain Resort

Williamstown Motel

Williamstown Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (318 reviews)
The price is P5,454
P6,093 total
includes taxes & fees
May 3 - May 4
Williamstown Motel
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.

Choose what matters most at family-friendly hotels in The Berkshires

Family-friendly hotels with free breakfast in The Berkshires

Family-friendly hotels with pools in The 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 The Berkshires Hotel Reviews

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