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The Berkshires Hotel Guide - 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 HotelLee
9.0 out of 10, Wonderful, (1,006 reviews)
- Family fun at lakeside retreat with kayaking, fishing, and premium TV channels.
"We wojld considrr returning in warmer weather with the kids/ grandkids as the environment is family friendly."
Melody
The price is €119
includes taxes & fees
28 May - 29 May
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
9.2 out of 10, Wonderful, (901 reviews)
"I wish I had known about this place when my kids were young."
JoAnn
The price is €120
includes taxes & fees
27 May - 28 May
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires by IHGPittsfield
9.4 out of 10, Exceptional, (96 reviews)
- Splash into family fun with indoor pool and hot tub—just minutes from Bousquet Ski Area and Tanglewood Music Centre.
"Room was clean, bed was comfortable, pool was nice, breakfast and coffee were good!"
Haley
The price is €122
includes taxes & fees
28 May - 29 May
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & SuitesPittsfield
8.6 out of 10, Excellent, (1,002 reviews)
- Berkshire family fun with free breakfast and ski-area adventures just minutes from winter sports and hiking trails.
"We have a dog traveling with us. It is really pet friendly. Love it!"
Yan
The price is €106
includes taxes & fees
26 May - 27 May
9.2 out of 10, Wonderful, (907 reviews)
"Friendly hotel workers, great breakfast, and my daughter loved the lobby decor. Perfect for a mother-daughter weekend away!"
Janice
The price is €80
includes taxes & fees
31 May - 1 Jun
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, (781 reviews)
- Families splash into fun at this Berkshires hotel with indoor pool, game arcade, and cosy rooms—all nestled near Ski Butternut.
"Staff are so friendly "
Mary Cay
The price is €163
includes taxes & fees
28 May - 29 May
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
8.0 out of 10, Very good, (1,001 reviews)
- Family adventures await with a heated indoor pool, kid-friendly dining, and spacious suites in the heart of Pittsfield.
"kids had so much fun"
Kristen
The price is €117
includes taxes & fees
31 May - 1 Jun
Travelodge by Wyndham Great Barrington Berkshires
Travelodge by Wyndham Great Barrington BerkshiresGreat Barrington
7.6 out of 10, Good, (580 reviews)
- Escape with the kids to this quiet, comfortable motel where family stays come with free beds and cots in immaculately clean rooms.
"Really nice little family business. Ty! "
Raymond
The price is €72
includes taxes & fees
25 May - 26 May
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, (1006)
The price is €119
includes taxes & fees
28 May - 29 May
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
9.2 out of 10, Wonderful, (901)
The price is €120
includes taxes & fees
27 May - 28 May
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
Vacation Village in the Berkshires
8/10 Good
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