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210 Family Entertainers serving Winchester, VA

Featured

  • Leesburg, VA
  • Photo Booths / Family Entertainment
  • 33 miles from Winchester
  • Starts at $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...

Oyster Eye Design Face Painting

5.0 (6)
Top Performer
8 Verified bookings

  • Charles Town, WV
  • Face Painter / Family Entertainment
  • 18 miles from Winchester
  • $275 – $600 per event

Brian B. said “Cassidy was so fantastic! Her artistic talent is amazing but more importantly she’s a people person. She connected with each of her “canvases” and brought out their personalities in her art. Beyond...”

Four of Hearts Illusion

4.92 (3)
2 Verified bookings

  • Winchester, VA
  • Magician / Family Entertainment
  • Contact for pricing

Clare P. said “I hired J. to provide strolling magic during my wedding cocktail hour. He was early to his gig and was a crowd pleaser. All the wedding guests raved about him and he made the cocktail hour an...”

Chuck Thomas

5.0 (8)
7 Verified bookings

  • Inwood, WV
  • Magician / Family Entertainment
  • 14 miles from Winchester
  • $200 – $1,000 per event

Jamie C. said “Great communication, reliable, funny, engaging with the residents, and a great vendor to work with!”

Sweet Expressions

5.0 (2)
7 Verified bookings

  • Front Royal, VA
  • Face Painter / Family Entertainment
  • 19 miles from Winchester
  • Contact for pricing

Nicole H. said “She was very talented and exceeded expectations! Thank you!”

C.C's Photobooths

5.0 (1)
6 Verified bookings

  • Aldie, VA
  • Photo Booths / Family Entertainment
  • 32 miles from Winchester
  • Starts at $300

Susan H. said “Students and staff loved the results of the photobooth. Highly recommended”

Sly's Magic - #1 in Corporate and Adult Magic

5.0 (4)
7 Verified bookings

  • Ashburn, VA
  • Magician / Family Entertainment
  • 38 miles from Winchester
  • $300 – $2,000 per event

Varun L. said “Very entertaining show. Both adults and kids enjoyed it. Sly was able to engage the audience throughout the show.”

Matthew Draws Stuff

5.0 (5)
7 Verified bookings

  • Warrenton, VA
  • Caricaturist / Family Entertainment
  • 38 miles from Winchester
  • Starts at $250

Cassidy G. said “He was so awesome at a birthday party! Everyone loved him!”

  • Berkeley Springs, WV
  • Face Painter / Family Entertainment
  • 31 miles from Winchester
  • Starts at $150 per hour

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...”
Featured

Miss Dianne Storyteller Extraordinaire

4.64 (9)
27 Verified bookings

  • Winchester, VA
  • Arts/Entertainment Speaker / Family Entertainment
  • $50 – $200 per event

Sharon H. said “Mrs Santa stole the show with her presentation of Twas the Night Before Christmas”

  • Leesburg, VA
  • Event Planner / Family Entertainment
  • 33 miles from Winchester
  • Starts at $2,000

At Ol' Fashion Flare, we create unforgettable events through elegant design, seamless planning, and exceptional hospitality. From weddings and 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.