Winston - Salem Kid friendly Vacations

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Top Kid friendly vacation packages in Winston - Salem

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Winston Salem - University

DoubleTree by Hilton Winston Salem - University

$907
per person
Oct 10 - Oct 17
found 1 hour ago
Roundtrip non-stop flight included
Orlando (MCO) to Greensboro (GSO)
8.4/10 Very Good! (1,003 reviews)
Kimpton Cardinal Hotel by IHG

Kimpton Cardinal Hotel by IHG

$924
per person
Sep 10 - Sep 14
found 4 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Greensboro (GSO)
9/10 Wonderful! (1,003 reviews)
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3 Night Kid friendly vacations in Winston - Salem

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Winston Salem - University

DoubleTree by Hilton Winston Salem - University

$809
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Greensboro (GSO)
8.4/10 Very Good! (1,003 reviews)
Kimpton Cardinal Hotel by IHG

Kimpton Cardinal Hotel by IHG

$809
per person
Oct 30 - Nov 2
found 18 hours ago
Roundtrip flight included
Chicago (CHI) to Greensboro (GSO)
9/10 Wonderful! (1,003 reviews)
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4 Night Kid friendly vacations in Winston - Salem

Price found within the past 48 hours. Click for updated prices.
Hawthorne Inn and Conference Center

Hawthorne Inn and Conference Center

$517
per person
Sep 10 - Sep 14
found 4 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Greensboro (GSO)
8.6/10 Excellent! (1,176 reviews)
The Historic Brookstown Inn, Trademark Collection by Wyndham

The Historic Brookstown Inn, Trademark Collection by Wyndham

$782
per person
Sep 10 - Sep 14
found 4 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Greensboro (GSO)
9.6/10 Exceptional! (1,003 reviews)
Village Inn Clemmons/Winston Salem, Trademark by Wyndham

Village Inn Clemmons/Winston Salem, Trademark by Wyndham

$534
per person
Sep 10 - Sep 14
found 4 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Greensboro (GSO)
8.4/10 Very Good! (1,003 reviews)
This is my go to when I’m in town which is once or twice a year.

Reviewed on Aug 5, 2026

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FAQs: family vacation packages in Winston - Salem

How can I find the best family vacation packages in Winston - Salem?

For fam-tastic vacation packages in Winston - Salem, 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 Winston - Salem 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 Winston - Salem cost?

You could book your amazing family trip to Winston - Salem just $517. 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 Winston - Salem 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 Winston - Salem?

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 Winston - Salem 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 Winston - Salem landmarks to save cash. Whenever you wish to travel, sort your search results by deals for the most brilliant bargains.

Can I book a Winston - Salem 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 Winston - Salem 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.

Things to do

Winston-Salem True Crime Tour

Winston-Salem True Crime Tour

$19
per adult
Winston-Salem True Crime Tour
Carolina History & Haunts Winston-Salem Historical Ghost Tour

Carolina History & Haunts Winston-Salem Historical Ghost Tour

$26
per adult
100% of travellers recommend
Carolina History & Haunts Winston-Salem Historical Ghost Tour
See all activities in Winston - Salem

More vacations you might like

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