Family friendly Hotels in The Berkshires, Massachusetts
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Check availability on The Berkshires Family friendly Hotels
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Aug 8 - Aug 9Tomorrow
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Aug 14 - Aug 16In two weeks
Aug 21 - Aug 23Our top choices for The Berkshires family-friendly hotels
1. Holiday Inn Club Vacations Oak 'n Spruce Resort
Holiday Inn Club Vacations Oak 'n Spruce ResortSouth Lee
P6,528
P8,484 total
includes taxes & fees
Sep 8 - Sep 9
2. The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection HotelLee
- Family fun at lakeside retreat with kayaking, fishing, and premium TV channels.
P8,186
P9,144 total
includes taxes & fees
Sep 7 - Sep 8
3. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHGPittsfield
- Splash into family fun with indoor pool and hot tub—just minutes from Bousquet Ski Area and Tanglewood Music Center.
P7,985
P8,919 total
includes taxes & fees
Sep 7 - Sep 8
4. Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & SuitesPittsfield
- Berkshire family fun with free breakfast and ski-area adventures just minutes from winter sports and hiking trails.
P6,932
P7,743 total
includes taxes & fees
Aug 30 - Aug 31
5. Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
- Family adventures await with a heated indoor pool, kid-friendly dining, and spacious suites in the heart of Pittsfield.
P7,724
P8,627 total
includes taxes & fees
Sep 1 - Sep 2
6. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/BerkshiresGreat Barrington
- Families splash into fun at this Berkshires hotel with indoor pool, game arcade, and cozy rooms—all nestled near Ski Butternut.
P11,865
P13,253 total
includes taxes & fees
Aug 13 - Aug 14
P10,301
P12,898 total
includes taxes & fees
Aug 11 - Aug 12
8. Comfort Inn & Suites East Greenbush - Albany
Comfort Inn & Suites East Greenbush - AlbanyCastleton-on-Hudson
P6,943
P7,706 total
includes taxes & fees
Sep 7 - Sep 8
View all properties
Family-friendly hotels with free breakfast in The Berkshires
Holiday Inn Club Vacations Oak 'n Spruce Resort
Holiday Inn Club Vacations Oak 'n Spruce ResortSouth Lee
P6,528
P8,484 total
includes taxes & fees
Sep 8 - Sep 9
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & SuitesPittsfield
P6,932
P7,743 total
includes taxes & fees
Aug 30 - Aug 31
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHGPittsfield
P7,985
P8,919 total
includes taxes & fees
Sep 7 - Sep 8
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
P7,724
P8,627 total
includes taxes & fees
Sep 1 - Sep 2
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection HotelLee
P8,186
P9,144 total
includes taxes & fees
Sep 7 - Sep 8
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/BerkshiresGreat Barrington
P11,865
P13,253 total
includes taxes & fees
Aug 13 - Aug 14
Travelodge by Wyndham Great Barrington Berkshires
Travelodge by Wyndham Great Barrington BerkshiresGreat Barrington
P4,804
P5,367 total
includes taxes & fees
Sep 1 - Sep 2
P5,376
P6,319 total
includes taxes & fees
Sep 8 - Sep 9
P4,093
P4,572 total
includes taxes & fees
Sep 7 - Sep 8
P6,629
P7,405 total
includes taxes & fees
Aug 17 - Aug 18
Family-friendly hotels with pools in The Berkshires
Holiday Inn Club Vacations Oak 'n Spruce Resort
Holiday Inn Club Vacations Oak 'n Spruce ResortSouth Lee
P6,528
P8,484 total
includes taxes & fees
Sep 8 - Sep 9
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHGPittsfield
P7,985
P8,919 total
includes taxes & fees
Sep 7 - Sep 8
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
P7,724
P8,627 total
includes taxes & fees
Sep 1 - Sep 2
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/BerkshiresGreat Barrington
P11,865
P13,253 total
includes taxes & fees
Aug 13 - Aug 14
P5,376
P6,319 total
includes taxes & fees
Sep 8 - Sep 9
P12,893
P14,401 total
includes taxes & fees
Aug 19 - Aug 20
P9,670
P10,801 total
includes taxes & fees
Aug 30 - Aug 31
P7,254
P8,102 total
includes taxes & fees
Aug 9 - Aug 10
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.
View all propertiesTop The Berkshires Hotel Reviews
Quality Inn Great Barrington
10/10 Excellent
"The breakfast area was small, so no seats available when it was crowded. But that's the only criticism."
The Yankee Inn
10/10 Excellent
"."
Vacation Village in the Berkshires
8/10 Good
"The 1 bedroom suite was comfortable and had everything we needed. The one thing that could be improved would be the mattress on the pull out couch. Needs to be thicker and less bumpy."
Hotel Downstreet, an Ascend Collection Hotel
10/10 Excellent
"Love this hotel for going to Mass MoCA"
The Red Lion Inn
8/10 Good
"Property is aging and needs attention. Still a nice place to stay."
Holiday Inn & Suites Pittsfield-Berkshires by IHG
8/10 Good
"Breakfast was delayed but the late arriving staff worked quickly to restore it. Quality of food was excellent"
The Little Lion
10/10 Excellent
"Great location. Functional and affordable. Pet friendly."
Jiminy Peak Mountain Resort
8/10 Good
"Jiminy Peak is located in an absolutely beatiful location in the Berkshires. And it has fun family-friendly summertime activities. But it could use some sprucing up. The pool liner is a little wrinkly and the hot tub is quite stained near the water line. In addition, our room had a nice 2-foot gouge in the wall seemingly caused by the corner of the armchair beneath it. It seems that could/should have been repaired before out arrival. And the dated counertops and fixtures are showing their age. That said, so am I! On the plus side: the iconic scenery, the friendly helpful staff, and the amenities. All in all, a good value for a family getaway. I would definitely recommend the prolerty overall."
Howard Johnson by Wyndham Lenox
10/10 Excellent
"Parking"