The Berkshires Kid friendly Vacations

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FAQs: family vacation packages in The Berkshires

How can I find the best family vacation packages in The Berkshires?

For fam-tastic vacation packages in The Berkshires, check the family-friendly filter and add child-charming amenities, like water parks and pools. Read reviews written by other broods to be sure your chosen stay packs plenty of rest and play.

How can I book family-friendly vacations in The Berkshires on a budget?

For family- and wallet-friendly trips, filter your search results by budget. You can also sort by price. When bringing the whole brigade on a budget, consider staying in low season or outside the city or. To save more coin, accommodation with a kitchen can be your friend—a bowl of pasta at home is always cheaper than feeding the team at a restaurant.

What does a family trip to The Berkshires cost?

You could book your amazing family trip to The Berkshires just . But with so many brilliant breaks on offer, there’s something for every wallet. Prices and availability are subject to change. Additional terms may apply.

Can I book an all-inclusive The Berkshires family vacation package?

Check the all-inclusive filter for an all-you-could-ever-wish-for family vacay. Click more of your favorite filters for even more extravagance. Perhaps an ocean view, spa, or hot tub. Maybe a water park, epic kids club, or activities galore.

How can I plan a fun family vacation in The Berkshires?

Search for stays with kid-satisfying extras, like water parks, and teenage-friendly free Wi-Fi, so they can post about all their vacation adventures for all their buddies back home. Book up local attractions, excursions, and experiences—and they might even put their phone down for a few minutes.

How can I find The Berkshires family vacation deals?

Delightful deals often dwell outside high season, so move your travel dates around for top deals. You can also book up a little away from the major The Berkshires landmarks to save cash. Whenever you wish to travel, sort your search results by deals for the most brilliant bargains.

Can I book a The Berkshires family vacation package with free cancellation and/or flexible dates?

Free cancellation makes for a hassle-free family vacation. Filter by payment option to find fully flexible trips, including buy now, pay later options.

Why should I book my The Berkshires family trip with Expedia?

You can easily find fun for all the family with the super-handy filters. It’s easy to build your dream kid-friendly vacation in just a few clicks. And you can bundle your accommodation, airfare, and car rental in just a few more.

Top Kid friendly The Berkshires Hotels

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
  • 13 min walk from Jiminy Peak Mountain Resort
Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (2,155 reviews)

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

Travelers say...
Great views

Reviewed on Nov 30, 2025

Vacation Village in the Berkshires
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
  • 25 min drive from Jiminy Peak Mountain Resort
Book a stay at this business-friendly hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,012 reviews)
Perfect

Reviewed on Dec 1, 2025

Hotel Downstreet, an Ascend Collection Hotel
Stay Berkshires

Stay Berkshires

2 out of 5
1146 Cold Spring Road Williamstown MA
  • 22 min drive from Jiminy Peak Mountain Resort
Stay at this hotel in Williamstown. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Margaret Lindley Park and Lindley Park are located ...
8.2/10 Very Good! (353 reviews)
Nice option to stay near MASS MOCA.

Reviewed on Dec 4, 2024

Stay Berkshires
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.