TOP Family Friendly Hotels in The Berkshires for 2026 - 𝗙𝗿𝗲𝗲 𝗖𝗮𝗻𝗰𝗲𝗹𝗹𝗮𝘁𝗶𝗼𝗻 on Select Hotels

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Our top choices for The Berkshires family-friendly hotels

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

Pittsfield

Splash into family fun with indoor pool and hot tub—just minutes from Bousquet Ski Area and Tanglewood Music Centre.

includes taxes & fees

16 Jul - 17 Jul

Comfort Inn & Suites East Greenbush - Albany

Castleton-on-Hudson

includes taxes & fees

12 Jul - 13 Jul

In-room safe, individually decorated, individually furnished, desk

Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

Berkshire family fun with free breakfast and ski-area adventures just minutes from winter sports and hiking trails.

includes taxes & fees

14 Jul - 15 Jul

Cozy Corner Motel

Williamstown

includes taxes & fees

26 Jul - 27 Jul

Hideaway Inn Mt. Snow

West Dover

includes taxes & fees

19 Jul - 20 Jul

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

South Lee

includes taxes & fees

29 Jul - 30 Jul

Williamstown Motel

Williamstown

includes taxes & fees

12 Jul - 13 Jul

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

Family fun at lakeside retreat with kayaking, fishing, and premium TV channels.

includes taxes & fees

12 Jul - 13 Jul

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Pool

Top The Berkshires Hotel Reviews

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."

The Red Lion Inn

10/10 Excellent

"Had a lovely 2 night stay at the Red Lion Inn. The front desk staff were very welcoming. The location was convenient to many nice shops and restaurants, as well as sites like the Norman Rockwell museum and the Divine Mercies chapel and grounds. This hotel is a wonderful blend of historic and modern..and the breakfast is great!"

Jiminy Peak Mountain Resort

8/10 Good

"The room was fine, the carpet was old and a bit musty. The fridge was helpful to have, and we used the coffee maker, would have preferred a Keurig. The bed was comfortable and the air conditioner worked fine. The furniture was nice, we liked the two separate bathroom sinks. Over a pleasant stay."

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Check availability on The Berkshires Family friendly Hotels

Our top choices for The Berkshires family-friendly hotels

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

Comfort Inn & Suites East Greenbush - Albany