Western Massachusetts Kid friendly Holidays

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FAQs: family holidays in Western Massachusetts

How can I find the best family-friendly holidays in Western Massachusetts?

At Expedia, it’s super-easy to find family-friendly holidays in Western Massachusetts in our vast inventory. Use our handy filters to find hotels and resorts with the best reviews, most amenities and lowest price tags. You can also hunt out great flights and smashing deals on car hire, so you can book the whole shebang in one place.

Are there any cheap Western Massachusetts family holidays?

Avoid forking out for multiple hotel rooms by booking a villa or apartment with a kitchen and give your brood plenty of space and all the meals they love at a fraction of the cost. Find the most affordable family holidays by filtering your search by price. Generally, Western Massachusetts family getaways start at . Prices and availability are subject to change and additional terms may apply.

Can I book an all-inclusive Western Massachusetts family holiday package?

All-inclusive holidays can keep the costs down when you’re travelling as a family. Think unlimited mocktails for the little'uns and double doses of gin for the bigguns. Use our all-inclusive filter to see what’s available in Western Massachusetts and book the whole package in just a few clicks.

How can I book the best family activity holiday in Western Massachusetts?

Family holidays are all about spending quality time together, laughing, playing and bonding as you try new things. Pack your trip full of family activities they’ll love and make memories that’ll last a lifetime.

Can I find luxury family holidays in Western Massachusetts?

To treat the kids to a luxury holiday they’ll never forget, take a look at the most indulgent hotels and resorts in Western Massachusetts by using our 5-star filter. To really travel in style, use the first-class filter to find the best flights, too.

How can I search for Western Massachusetts family holiday deals?

Start by entering your dates, then use the family-friendly filter to narrow down your search to show the best available Western Massachusetts family holiday deals. If your travel dates are flexible, play around to see if you can find cheaper options or more availability at different times.

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

Plans change, so booking a family holiday with free cancellation is a great way to ensure you don’t lose out if they do. Use the fully refundable and reserve now pay later filters to find flexibility. Make sure you always check terms and conditions, too.

Why should I book my Western Massachusetts family trip with Expedia?

Forget family fights and start thinking about family flights. Our huge selection of easy to browse family-friendly holidays means you can find and book your dream family trip to Western Massachusetts in no time.

Top Kid friendly Western Massachusetts Hotels

Vacation Village in the Berkshires
Vacation Village in the Berkshires
3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
  • 1 hour drive from Six Flags New England
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness centre and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,847 reviews)

Families like: Kids' swimming pool, playground, games room, skiing nearby

Travellers say...
"amazing for the price and overall SOOO clean"

Reviewed on 28 Jun 2025

Vacation Village in the Berkshires
La Quinta Inn & Suites by Wyndham Springfield MA
La Quinta Inn & Suites by Wyndham Springfield MA
3 out of 5
100 Congress Street, Springfield, MA
  • 12 min drive from Six Flags New England
Stay at this family-friendly hotel in Springfield. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. ...
8/10 Very Good! (1,269 reviews)

Families like: Indoor pool, games room, cots, rollaway/extra beds

Travellers say...
"Staff was all super friendly and helpful. Location was where I needed it to be. Renovation was going on, which meant I had to go up 2 floors on the elevator to find a working ice machine. Pool is not as attractive in person as it is in the photo."

Reviewed on 30 Jun 2025

La Quinta Inn & Suites by Wyndham Springfield MA
D. Hotel Suites & Spa
D. Hotel Suites & Spa
3 out of 5
1 Country Club Rd, Holyoke, MA
  • 39 min drive from Six Flags New England
Stay at this 3-star spa hotel in Holyoke. Enjoy a full-service spa, 2 restaurants and room service. Our guests praise the breakfast and the pool in their reviews. ...
9.2/10 Wonderful! (2,282 reviews)
"Room was clean and staff was wonderful, only issue was loose toilet seat, and you needed to hold the handle down to flush toilet"

Reviewed on 2 Jul 2025

D. Hotel Suites & Spa
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.

More holidays you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.