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Find Family Hotels in The Berkshires, MA

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Our top choices for The Berkshires family-friendly hotels

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, (998)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is ¥13,772
¥15,383 total
includes taxes & fees
Jan 2 - Jan 3, 2026
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, (1000)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is ¥16,214
¥18,111 total
includes taxes & fees
Jan 5 - Jan 6, 2026
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, (759)
"Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again."
United States
Dinh
The price is ¥21,079
¥23,544 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Fairfield Inn & Suites by Marriott Great Barrington Lenox/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, (808)
"Convenient location, very roomy, well equipped kitchen. "
United States
Carolyn
The price is ¥19,955
¥25,344 total
includes taxes & fees
Jan 4 - Jan 5, 2026
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, (1000)
"Very friendly and good Breakfast."
United States
Jesse
The price is ¥14,722
¥16,445 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Best Western Plus Berkshire Hills Inn & Suites

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (14)
"Rooms were very clean and spacious."
United States
Morgan
The price is ¥21,079
¥23,545 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Element Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (592)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
The price is ¥21,703
¥24,242 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Courtyard by Marriott Lenox Berkshires

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (374)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn

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, (69)
"This is a brand new hotel. Everything was perfect, from check-in to check-out. We especially enjoyed the hot tub and pool. "
United States
Joan
The price is ¥19,135
¥21,374 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (17)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
The price is ¥39,347
¥49,182 total
includes taxes & fees
Jan 26 - Jan 27, 2026
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.

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

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