- Leesburg, VA
- Photo Booths / Family Entertainment
- 33 miles from Winchester
- $499+
MoovBooth is the Hype Man for your next event. Our engaging specialized 360 video and photo booth services enhance your event experience and create shareable...
The 13 Best Family Entertainers for hire in Winchester, VA
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206 Family Entertainers serving Winchester, VA
- Inwood, WV
- Magician / Family Entertainment
- 14 miles from Winchester
- $200 - $1000
Jamie C. said
“Great communication, reliable, funny, engaging with the residents, and a great vendor to work with! ”
- Front Royal, VA
- Face Painter / Family Entertainment
- 19 miles from Winchester
- Contact for rates
Allison H. said
“Pamela was awesome! She is ridiculously talented - everyone at our event was saying they’d never seen such beautiful designs. She was so wonderful with the kids at our event - many of whom were... ”
- Aldie, VA
- Photo Booths / Family Entertainment
- 32 miles from Winchester
- $300 and up
Susan H. said
“Students and staff loved the results of the photobooth. Highly recommended ”
- Ashburn, VA
- Face Painter / Family Entertainment
- 38 miles from Winchester
- Starting at $140/hour, 2 hour minimum
Lynn H. said
“We are so happy we hired Fairy Tree painting for our 6 hour fundraising event. Melissa worked non-stop through the entire 6 hours. Both the kids and their parents loved the face painting designs... ”
- Ashburn, VA
- Magician / Family Entertainment
- 38 miles from Winchester
- $300 and up
Varun L. said
“Very entertaining show. Both adults and kids enjoyed it. Sly was able to engage the audience throughout the show. ”
- Warrenton, VA
- Caricaturist / Family Entertainment
- 38 miles from Winchester
- $250-$600+
Catherine P. said
“Matthew was very punctual, arriving at the venue for our wedding reception with plenty of time to set up his work station. He was courteous and polite to all of our guests, and drew awesome... ”
- Winchester, VA
- Photo Booths / Family Entertainment
- $400+
Elevate your event to the next level with a photo booth! Our photo booth services include two different booths to choose from. Our digital package is equipped...
- Winchester, VA
- Photo Booths / Family Entertainment
- $400 and up
We provide a photo booth experience for you and your guests to enjoy at your special event.
Four of Hearts Illusion
- Winchester, VA
- Magician / Family Entertainment
- $300-$2500
Kristen V. said
“Having been a few years since the last time I has seen a "Magic Show", I wasn't expecting what was in store. I had brought my girlfriend and knew in the first 5 minutes buying tickets was a great... ”
Donna Mays Design
- Berkeley Springs, WV
- Face Painter / Family Entertainment
- 31 miles from Winchester
- Contact for rates
Cary H. said
“Our family is so pleased with the face painting the children received at my son's 5th birthday. The designs were very detailed and didn't take very long. Donna was so very kind with all the... ”
- Leesburg, VA
- Event Planner / Family Entertainment
- 33 miles from Winchester
- $2,000 and up
At Ol’ Fashion Flare, we specialize in transforming events into extraordinary experiences—anywhere! Whether you’re planning an elegant wedding, a corporate...
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About booking Family Entertainment in Winchester, VA
Family events come to life with entertainment that delivers fun, laughter, and unforgettable memories for every generation. The right performers set the tone, whether it’s a lively musician or DJ getting everyone dancing, or a magician who amazes kids and adults alike. From face painters and balloon twisters to jugglers, clowns, and interactive games, professional entertainers transform birthdays, picnics, reunions, and community gatherings into joyful celebrations.
The cost of hiring family entertainers in Winchester, Virginia will vary depending on the type of entertainment, their experience, and the length of the performance. Services like balloon twisting may be cheaper than more involved performances like magic shows. Contact the local acts above to discuss your event and receive a customized quote.
As you explore Winchester family entertainers, check out profiles to learn about their party packages, browse photos, and watch promotional videos. Then, read reviews from past clients to see how they’ve brought the fun to similar events. When requesting a quote, communicate things like your event location, audience size, performance space, and desired atmosphere to get the most accurate pricing.
Once you find the performer you want to hire, finalize the booking on GigSalad. Our full-service platform makes it easy to book family-friendly entertainment. You can message the acts, confirm the details of your agreement, and make a secure payment all in one place. Every GigSalad event is covered by our Worry-Free Guarantee, so you can rest easy knowing we’ve got your back. Just sit back and let the family fun begin!
Family Entertainment serving the Winchester, VA area
These Family Entertainment serve the wider Winchester and Winchester City county area and travel to Stephenson, Clear Brook, Brucetown, Stephens City, Boyce, Ridgeway, White Post, Berryville, Millwood, Gore, Cross Junction, Bunker Hill, Summit Point, Middletown, Middleway, Gerrardstown, High View, Inwood, Glengary, Rippon, Good, Capon Bridge, Paris, Star Tannery, Strasburg, Capon Springs, Charles Town, Bloomery, Ranson, and Bluemont.