Book Kid-Friendly Hotels in The Berkshires from $75

Name: Jiminy Peak Mountain Resort
Price range: $231 total
Rating: 8.2

Find & compare hotels, resorts and vacation rentals for the whole family

Top The Berkshires Kid Friendly Hotels

Williamstown Motel

295 Main Street Williamstown MA

This motel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of ...

9.2/10 Wonderful! (314 reviews)

Room was very clean. Spoke to staff on the way in who was very courteous about our late arrival. Continental breakfast was accommodative. Free visitor materials were helpful. 😊

Reviewed on Nov 23, 2025

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Cozy Corner Motel

284 Sand Springs Rd. Rte 7 Williamstown MA

Fully refundableReserve now, pay when you stay

$88 total

per night

Jan 25 - Jan 26

This motel features a restaurant, a lazy river, and a bar/lounge. Families will appreciate the playground and barbecue grills. There's no skimping on freebies ...

9/10 Wonderful! (891 reviews)

Families like: Lazy river, playground, skiing nearby, free breakfast for the whole family

Travelers say...

Staff was very nice, property was well-maintained and up to date. Easy to get to, and good parking. Provided breakfast was a plus. Highly recommend.

Reviewed on Jan 18, 2026

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

Fully refundableReserve now, pay when you stay

$141 total

per night

Jan 26 - Jan 27

This condo features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks ...

8.6/10 Excellent! (2,211 reviews)

Families like: Kids pool, playground, game room, skiing nearby

Travelers say...

Room clean staff polite

Reviewed on Jan 18, 2026

Hotel Downstreet, an Ascend Collection Hotel

40 Main St North Adams MA

Fully refundable

$134 total

per night

Feb 4 - Feb 5

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 2 conference rooms, free WiFi in public areas, and express ...

8.6/10 Excellent! (1,000 reviews)

Staff was pleasant and helpful, room spacey and all immaculate .

Reviewed on Jan 11, 2026

Stay Berkshires

1146 Cold Spring Road Williamstown MA

A seasonal outdoor pool is featured at this hotel, along with free self parking. Guests will appreciate free perks like continental breakfast and WiFi in public ...

8.2/10 Very Good! (353 reviews)

Nice option to stay near MASS MOCA.

Reviewed on Dec 4, 2024

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Jiminy Peak Mountain Resort

37 Corey Rd Hancock MA

Fully refundableReserve now, pay when you stay

$231 total

per night

Jan 28 - Jan 29

Ski-in/ski-out access, 2 restaurants, and 2 outdoor tennis courts are all featured at this smoke-free condo resort. Take advantage of ski lessons, ski rentals ...

8.2/10 Very Good! (989 reviews)

This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the ...

Reviewed on Oct 5, 2025

Econo Lodge Lee - Great Barrington

980 Pleasant Street Lee MA

Fully refundableReserve now, pay when you stay

$75 total

per night

Jan 28 - Jan 29

This motel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Multilingual staff at the 24-hour front desk ...

6.2/10 (654 reviews)

Friendy, I like the decor of the room

Reviewed on Dec 23, 2025

Lantern House Motel

256 Stockbridge Road Great Barrington MA

A seasonal outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. A garden and a picnic area are also provided.

Avoid staying here if you can.

The fact that they require a vaccine card should be mentioned in their Hotels.com profile. Luckily for me I had it in my car. I don't mind if some hotel owners want to require it, but it should be pretty clearly stated. The owner told me that I didn't need to use the air conditioner, that I should ...

Reviewed on Nov 22, 2021

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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.

Hotels With Pools in The Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

249 Stockbridge Rd Great Barrington MA

$169 total

per night

Jan 27 - Jan 28

9.2/10 Wonderful! (763 reviews)

Hotels with Childcare in The Berkshires

Devonfield Inn B&B

85 Stockbridge Rd. Lee MA

$312 total

per night

Feb 16 - Feb 17

9.8/10 Exceptional! (134 reviews)

The Berkshires Kid-Friendly Hotels

It’s not a family vacation if you can’t bring the entire clan with you, is it? Next time you have a few days off from work, plan a family-friendly getaway. Set off on an adventure the entire family will love, and book your stay at one of the kid-friendly hotels in The Berkshires.

Your little ones are the most important thing in your life, so make sure they enjoy your accommodation as much as you do. From a kids-only room service menu (macaroni and cheese, anyone?) to special perks like in-room video game consoles, these lodgings provide a little something extra for the smaller members of your crew. The best family-friendly hotels in The Berkshires may even offer playgrounds and other activities to keep the kiddos busy. What’s more, some hotels provide a babysitting service so you can get a few hours to yourself!

Whether you’re traveling with one small child or hauling around your entire extended family, Travelocity is here to help. Let us hook you up with hotels for kids in The Berkshires that will keep your youngsters happy without breaking the bank. You can save even more when you bundle your flight and hotel together, so what are you waiting for? Grab your family and get ready to explore!