Book Kid-Friendly Hotels in The Berkshires from $85

Name: Jiminy Peak Mountain Resort
Price range: $160 total
Rating: 8.2

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

Top The Berkshires Kid Friendly Hotels

Hotel On North

297 North Street Pittsfield MA

Fully refundableReserve now, pay when you stay

$179 nightly

$200 total

Jun 14 - Jun 15

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the business center. There's ...

9.6/10 Exceptional! (864 reviews)

"Hotels Amazing stay here"

Reviewed on May 29, 2026

Williamstown Motel

295 Main Street Williamstown MA

Fully refundableReserve now, pay when you stay

$89 nightly

$99 total

Jun 15 - Jun 16

Total with taxes and fees

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! (324 reviews)

"Lovely old-fashioned motel, very clean, extremely friendly and helpful owner. Reasonably priced and well-located for a visit to Williamstown and Mass MOCA."

Reviewed on Jun 10, 2026

Cozy Corner Motel

284 Sand Springs Rd. Rte 7 Williamstown MA

Fully refundableReserve now, pay when you stay

$89 nightly

$100 total

Jun 18 - Jun 19

Total with taxes and fees

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 ...

9.2/10 Wonderful! (913 reviews)

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

Travelers say...

"From check-in to check-out everything for the stay was excellent. Kind and helpful staff, a very clean, bright and comfortable room with all amenities, and even a complimentary breakfast made this a 5-star winner!"

Reviewed on Jun 11, 2026

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

Fully refundableReserve now, pay when you stay

$136 nightly

$152 total

Jun 14 - Jun 15

Total with taxes and fees

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 ...

8.8/10 Excellent! (2,392 reviews)

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

Travelers say...

"This is a big beautful modern condo complex about 20 mins outside Wiilamstown (to the north) or Pittsfield (to the south). Huge swimming pools - one indoors, one out. Beautiful views of the Berkshires. Quiet rural environment. I could hear the frogs singing and the cricketa chirp at night. Excellent ..."

Reviewed on Jun 8, 2026

Hotel Downstreet, an Ascend Collection Hotel

40 Main St North Adams MA

Fully refundable

$163 nightly

$182 total

Jun 14 - Jun 15

Total with taxes and fees

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 ...

8.8/10 Excellent! (1,009 reviews)

"Clean simple, functional, nice all day coffee tea station"

Reviewed on Jun 8, 2026

Jiminy Peak Mountain Resort

37 Corey Rd Hancock MA

Fully refundableReserve now, pay when you stay

$143 nightly

$160 total

Jun 14 - Jun 15

Total with taxes and fees

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

8.2/10 Very Good! (994 reviews)

"The property had a village square with a mountain coaster, alpine slide, giant swing and other family activities."

Reviewed on May 23, 2026

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.

8.2/10 Very Good! (455 reviews)

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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Econo Lodge Lee - Great Barrington

980 Pleasant Street Lee MA

Fully refundableReserve now, pay when you stay

$76 nightly

$85 total

Jun 25 - Jun 26

Total with taxes and fees

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 ...

6.4/10 (666 reviews)

"all good"

Reviewed on Jun 5, 2026

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

$186 nightly

$208 total

Jun 15 - Jun 16

Total with taxes and fees

9.4/10 Exceptional! (784 reviews)

Hotels with Childcare in The Berkshires

Devonfield Inn B&B

85 Stockbridge Rd. Lee MA

$329 nightly

$367 total

Jun 14 - Jun 15

Total with taxes and fees

10/10 Exceptional! (138 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!

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Recent The Berkshires Hotel Reviews By Fellow Wanderers

The Yankee Inn

4 out of 5

Posted 19 hours ago

Travelocity Verified Review

"The room was large, clean and comfortable. The location was near shopping and dining. The check in was quick and pleasant."

A verified traveler stayed at The Yankee Inn

The Red Lion Inn

4 out of 5

Posted 3 days ago

Travelocity Verified Review

"It is a charming, historic hotel. Dinner in the tavern was delicious and service was very good. The only thing we didn't like was the mattress, which needs to be replaced as it has divits. Other than that, it's a cool place that is fun to explore. Wish we were here longer to try out the pool. We did enjoy getting a cocktail from the bar and sitting in rockers on the front porch, watching the traffic go by."

A verified traveler stayed at The Red Lion Inn

Vacation Village in the Berkshires

5 out of 5

Posted 3 days ago

Travelocity Verified Review

"This is a big beautful modern condo complex about 20 mins outside Wiilamstown (to the north) or Pittsfield (to the south). Huge swimming pools - one indoors, one out. Beautiful views of the Berkshires. Quiet rural environment. I could hear the frogs singing and the cricketa chirp at night. Excellent value for the money. Friendly staff. I got a one-bdrm condo for the price of a standard hotel. No grocery atores nearby some come with supplies if you plan to cook."

A verified traveler stayed at Vacation Village in the Berkshires