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Family friendly Hotels in The Berkshires, Massachusetts
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Check availability on The Berkshires Family friendly Hotels
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 HotelLee
9.0 out of 10, Wonderful, (1,000 reviews)
- 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
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 IHGSouth Lee
9.0 out of 10, Wonderful, (886 reviews)
The price is P7,832
P9,947 total
includes taxes & fees
May 4 - May 5
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & SuitesPittsfield
8.6 out of 10, Excellent, (1,001 reviews)
- 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
The price is P4,854
P5,720 total
includes taxes & fees
May 3 - May 4
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/BerkshiresGreat Barrington
9.4 out of 10, Exceptional, (778 reviews)
- 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
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires by IHGPittsfield
9.2 out of 10, Wonderful, (91 reviews)
- 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 & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
8.0 out of 10, Very Good, (1,000 reviews)
- 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
Travelodge by Wyndham Great Barrington Berkshires
Travelodge by Wyndham Great Barrington BerkshiresGreat Barrington
7.6 out of 10, Good, (577 reviews)
- 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
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.
Family-friendly hotels with free breakfast in The Berkshires
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection HotelLee
9.0 out of 10, Wonderful, (1000)
The price is P7,011
P7,831 total
includes taxes & fees
May 5 - May 6
Family-friendly hotels with pools in The 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 IHGSouth Lee
9.0 out of 10, Wonderful, (886)
The price is P7,832
P9,947 total
includes taxes & fees
May 4 - May 5
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
The Little Lion
10/10 Excellent
