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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, (1,001 reviews)
  • cleanliness
    Family fun at lakeside retreat with kayaking, fishing, and premium TV channels.
The price is ₩196,547
₩219,550 total
includes taxes & fees
Jun 8 - Jun 9
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
9.2 out of 10, Wonderful, (904 reviews)
The price is ₩205,512
₩259,518 total
includes taxes & fees
Jun 7 - Jun 8
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 ₩170,417
₩190,355 total
includes taxes & fees
Jun 8 - Jun 9
Best Western Plus Berkshire Hills Inn & Suites

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (912 reviews)
The price is ₩129,652
₩152,548 total
includes taxes & fees
Jun 9 - Jun 10
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, (782 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 ₩298,307
₩333,209 total
includes taxes & fees
Jun 29 - Jun 30
Fairfield Inn & Suites by Marriott Great Barrington 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)
  • cleanliness
    Family adventures await with a heated indoor pool, kid-friendly dining, and spacious suites in the heart of Pittsfield.
The price is ₩186,969
₩208,838 total
includes taxes & fees
Jun 15 - Jun 16
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Williamstown Motel

Williamstown Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (321 reviews)
The price is ₩151,720
₩169,472 total
includes taxes & fees
Jun 8 - Jun 9
Williamstown Motel

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
3.0 star property
Hancock
8.2 out of 10, Very Good, (992 reviews)
  • cleanliness
    Family-friendly mountain resort with pools and skiing thrills for all ages in Jiminy Peak.
The price is ₩219,305
₩244,964 total
includes taxes & fees
Jun 10 - Jun 11
Jiminy Peak Mountain Resort

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (665 reviews)
  • cleanliness
    Family-friendly budget escape with free miniature golf and breakfast, minutes from Berkshire Botanical Garden.
The price is ₩103,085
₩115,147 total
includes taxes & fees
Jun 18 - Jun 19
Econo Lodge Lee - Great Barrington

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (582 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 ₩121,070
₩135,236 total
includes taxes & fees
Jun 7 - Jun 8
Travelodge by Wyndham Great Barrington 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.

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.

Find out more about The Berkshires

Family friendly things to do in The Berkshires

The Berkshires is a paradise of family-friendly activities that make it a perfect getaway for those traveling with children. Start your adventure at the Berkshire Museum in Pittsfield, where interactive exhibits and live animal displays ignite curiosity and encourage learning. For outdoor enthusiasts, the picturesque Tanglewood Music Center offers not only concerts but also beautiful grounds for picnics and exploration, where kids can run freely and enjoy the fresh air. Take a family hike up to Mount Greylock, the highest peak in Massachusetts, where stunning vistas reward your efforts and photo opportunities . In the summer, the Lenox Town Beach provides a refreshing spot for swimming and relaxation, while families can also enjoy canoeing or paddleboarding on the serene waters of nearby lakes. When it comes to accommodations, the area around Lenox boasts charming family-friendly hotels like the Blantyre, which offers spacious rooms and a welcoming atmosphere ideal for families. After a day of adventure, unwind by the pool or indulge in the on-site dining, where kids' menus and attentive service ensure that everyone feels pampered. The Berkshires blends culture, nature, and comfort, creating an enriching experience for families looking to explore together.

Top The Berkshires Hotel Reviews