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The Berkshires Hotel Guide - 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

Indoor pool

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (127 reviews)
  • cleanliness
    Splash into family fun with indoor pool and hot tub—just minutes from Bousquet Ski Area and Tanglewood Music Centre.
The price is €134
includes taxes & fees
16 Jul - 17 Jul
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Exterior

Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany
2.5 star property
Castleton-on-Hudson
8.6 out of 10, Excellent, (1,011 reviews)
The price is €123
includes taxes & fees
12 Jul - 13 Jul
Comfort Inn & Suites East Greenbush - Albany
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)

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, (1,004 reviews)
  • cleanliness
    Berkshire family fun with free breakfast and ski-area adventures just minutes from winter sports and hiking trails.
The price is €132
includes taxes & fees
12 Jul - 13 Jul
Best Western Plus Berkshire Hills Inn & Suites
Exterior

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (925 reviews)
The price is €91
includes taxes & fees
26 Jul - 27 Jul
Cozy Corner Motel
Property amenity

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow
3.0 star property
West Dover
8.6 out of 10, Excellent, (116 reviews)
The price is €86
includes taxes & fees
19 Jul - 20 Jul
Hideaway Inn Mt. Snow
Arcade

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, (929 reviews)
The price is €170
includes taxes & fees
22 Jul - 23 Jul
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
BBQ/picnic Area

Williamstown Motel

Williamstown Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (330 reviews)
The price is €97
includes taxes & fees
13 Jul - 14 Jul
Williamstown Motel
Lake

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,008 reviews)
  • cleanliness
    Family fun at lakeside retreat with kayaking, fishing, and premium TV channels.
The price is €228
includes taxes & fees
12 Jul - 13 Jul
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior

Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.4 out of 10, Exceptional, (1,002 reviews)
The price is €236
includes taxes & fees
22 Jul - 23 Jul
Simsbury 1820 House
Free daily buffet breakfast

Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield
2.5 star property
Westfield
7.2 out of 10, Good, (957 reviews)
  • cleanliness
    Enjoy a family getaway with free breakfast and kid-friendly amenities at this peaceful Westfield hotel near shopping.
The price is €99
includes taxes & fees
2 Aug - 3 Aug
Quality Inn Westfield - Springfield
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.
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Choose what matters most at family-friendly hotels in The Berkshires

Breakfast included
Pool

Family-friendly hotels with free breakfast in The Berkshires

Indoor pool
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (127)
The price is €134
includes taxes & fees
16 Jul - 17 Jul
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
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Family-friendly hotels with pools in The Berkshires

Indoor pool
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (127)
The price is €134
includes taxes & fees
16 Jul - 17 Jul
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
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 properties

Top The Berkshires Hotel Reviews

The Yankee Inn

The Yankee Inn

8/10 Good
"The hotel is a few minutes from Tanglewood and the Berkshire hotspots. Super friendly staff. Very accommodating. The place is a bit dated, but that has a retro charm like places on the Cape. The grounds are lovely. The breakfast is like other hotel breakfast. Lots of options: cereal, oatmeal, eggs, sausage, hard boiled eggs, fruit, bread, pastries, etc. My only complaint was the bed, which had a mattress in desperate need of replacement. We referred to it as sleeping in the valley because it made us roll to the center. It was also really high, which was challenging in an accessible room. I called and they had a stool for me within 5 minutes so we made it work. The people were so nice so I hate adding a complaint in my review. We would have asked for a room change but were there over a holiday weekend and I was pretty sure there wouldn’t be another option. The pluses outweigh the negatives so we had a good time."
Jean 3-night trip
Posted 10 hours ago
The Yankee Inn

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