Book Kid-Friendly Hotels in The Berkshires

Name: Jiminy Peak Mountain Resort
Rating: 8.2

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Top The Berkshires Kid Friendly Hotels

Williamstown Motel

295 Main Street, Route 2, Williamstown, MA

Fully refundableReserve now, pay when you stay

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! (267 reviews)

Comfortable, Clean, and Convenient

"The room was very comfortable, totally clean, and the motel is conveniently located halfway between Williams and MassMOCA. While some of the decor you can see in the photos might not be entirely up-to-date, don't let that discourage you. The property is really well maintained, and the room was a ..."

Reviewed on Jun 6, 2025

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Cozy Corner Motel

284 Sand Springs Rd. Rte 7, Williamstown, MA

Fully refundableReserve now, pay when you stay

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! (822 reviews)

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

Travelers say...

"Great classic motel. Clean. Friendly, helpful staff."

Reviewed on Jun 12, 2025

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Vacation Village in the Berkshires

276 Brodie Mountain Rd, Williamstown, MA

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! (1,825 reviews)

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

Travelers say...

"Love it's peace and beautiful~"

Reviewed on Jun 13, 2025

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Hotel Downstreet, Ascend Hotel Collection

40 Main St, North Adams, MA

Fully refundableReserve now, pay when you stay

This hotel features an indoor pool and a 24-hour gym. Enjoy the hot tub and perks like free self parking and free WiFi. A communal living room, express check-out, ...

8.6/10 Excellent! (1,002 reviews)

"Beautiful and clean rooms. Very professional staff."

Reviewed on Jun 14, 2025

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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

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! (933 reviews)

"Summer stay not during ski season. Staff very helpful, welcoming, friendly. Room was clean and nice although some people might consider the main lodging building where I stayed would be outdated. But it was a very good experience all around. Beautiful natural surroundings all around the area so it’s ..."

Reviewed on Jun 9, 2025

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Econo Lodge Lee - Great Barrington

980 Pleasant Street, Lee, MA

Fully refundableReserve now, pay when you stay

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 (597 reviews)

Good Little Hotel

"For the price, it's a great deal. The hot water is not hot at bedtime (I was gone most of the time, only needed the place to sleep, so I got up very early to take my showers)"

Reviewed on May 26, 2025

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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

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9.2/10 Wonderful! (703 reviews)

Hotels with Childcare in The Berkshires

Devonfield Inn B&B

85 Stockbridge Rd., Lee, MA

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9.8/10 Exceptional! (126 reviews)

Book a stay at the best kid-friendly hotels in The Berkshires

How much does it cost to stay in a family hotel in The Berkshires?

You can book a stay at a kid-friendly resort in The Berkshires from just per night. Our prices range up per night if you want to enjoy the high life.

How many family-friendly hotels are there in The Berkshires?

With over 1,095 hotels in The Berkshires, you have a great selection of kid-friendly places to stay. Whether you’re looking for a cheap-and-cheerful property with plenty of space or an activity-filled kid-friendly resort, there’s a getaway to suit your style and your budget at Travelocity.

What is Travelocity’s cancellation policy for family hotels in The Berkshires?

We offer free cancellation on select hotels. Policies can vary per property so it's best to check before you book. If you need to amend or cancel your vacation, just visit our Customer Service Portal. 

What are the best kid-friendly hotels in The Berkshires?

At Travelocity, you can book the best family-friendly The Berkshires hotel for you and your family by filtering your search by price, property type, and a range of amenities such as breakfast included or free airport shuttle. Use the map to see where the hotels are and the attractions they’re near.

What should I expect in the family-friendly hotels in The Berkshires?

When you book a kid-friendly The Berkshires resort, you can expect fun for all the family. Think pools, waterparks, and hot tubs. Think babysitting, kids’ menus, games rooms, and sport facilities—discover your ideal family vacation. Many resorts keep the kids happy, so you can indulge in bars, restaurants, and spas. Check details for each property as offers may vary.

How can I find family hotel deals in The Berkshires?

Just enter your travel dates and sort your results by price. You can even filter your results by budget, so you’ll only see the deals that are right for your pocket. It’s easy to find great deals on family-friendly hotels in The Berkshires with Travelocity. 

When is the cheapest time to go to The Berkshires with your family?

The cheapest time to visit The Berkshires is usually .

When is the best time to go to The Berkshires with your kids?

The most popular months are and are great for booking in at a The Berkshires kid-friendly resort. If you want a quieter vacation—or the kids aren’t in school yet— are usually less busy, but you can find incredible deals all year round with Travelocity. 

Why book a The Berkshires child-friendly hotel with Travelocity?

Because we search the entire market, so you don’t have to. You’ll find great deals on everything from weekend trips to two-week family vacations. Whatever your budget or your wish list, we’ve got what you’re looking for.