Banner image for Holiday Party Entertainment
0%

Just a couple more things…

We need some additional information to ensure we find the perfect talent for your event!

339 Holiday Party Entertainers serving Winchester, VA

Featured

Santa Frank

4.98 (32)
Top Performer
71 Verified bookings

  • Charles Town, WV
  • Santa Claus / Holiday Party Entertainment
  • 18 miles from Winchester
  • Contact for pricing

Klaudia A. said “We had a lovely time. Santa was easy going and kind - chatting up the kids and keeping things stress free for the parents. Definitely, will recommend to family and friends. ”

Santa Michael

5.0 (4)
Top Performer
13 Verified bookings

  • Martinsburg, WV
  • Santa Claus / Holiday Party Entertainment
  • 22 miles from Winchester
  • Starts at $125 per hour

Kelsey S. said “Both Santa and Mrs. Claus were both friendly, patient, and made the whole experience! 10/10 best around! Can't wait to have them next year! ”

Kathy Farmer & Friends Jazz Band

5.0 (3)
3 Verified bookings

  • Ashburn, VA
  • Jazz Band / Holiday Party Entertainment
  • 38 miles from Winchester
  • Starts at $500

Josh J. said “We had the absolute pleasure of having Kathy and her piano player, Zenon, provide live jazz for our Night to Shine Respite Room, and they were wonderful. This space was specifically for the caregivers...”

The Daniel Kelly II Trio

5.0 (2)
2 Verified bookings

  • Winchester, VA
  • Jazz Band / Holiday Party Entertainment
  • $200 – $900 per event

Marlena N. said “The trio played for my parents 50th wedding anniversary party. They sounded great, looked professional and were extremely courteous. All the guests commented how they were the prefect for the...”

SantaBlueEyes

4 Verified bookings

  • Winchester, VA
  • Santa Claus / Holiday Party Entertainment
  • $200 per hour

Parades, Studio Sessions, indoor/outdoor activities, Home visits, Corporate events, Annual photos with Santa, Pet friendly, Elves and Mrs. Claus available,

Four of Hearts Illusion

4.92 (3)
2 Verified bookings

  • Winchester, VA
  • Magician / Holiday Party 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...”

Santa Al

1 Verified booking

  • Stephens City, VA
  • Santa Claus / Holiday Party Entertainment
  • 8 miles from Winchester
  • Contact for pricing

Santa Claus holiday performer accompanied by Mrs. Claus to make your Christmas holiday event memorable.

Box5 Santa

5.0 (3)
2 Verified bookings

  • Middletown, VA
  • Santa Claus / Holiday Party Entertainment
  • 13 miles from Winchester
  • Starts at $150

Jenn D. said “I can not say enough great things about Box5 Santa. He has joined us for multiple events and we have never been disappointed. Kids of all ages adore him! From his suit to his personality it is all...”

Chuck Thomas

5.0 (8)
7 Verified bookings

  • Inwood, WV
  • Magician / Holiday Party 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!”

Santa Claus Bill

4.43 (7)
7 Verified bookings

  • Front Royal, VA
  • Santa Claus / Holiday Party Entertainment
  • 19 miles from Winchester
  • Contact for pricing

Patricia M. said “Bill was terrific as Santa for our party of 50 with 20 children. He even brought his wife Mrs Claus who was very engaging and lovely with the children. We definitely recommend them!”

Santa Jerry

5.0 (6)
15 Verified bookings

  • Front Royal, VA
  • Santa Claus / Holiday Party Entertainment
  • 19 miles from Winchester
  • Starts at $300

Paige K. said “Santa Jerry brought the holiday spirit to our little elf and all of her friends. He communicated very well prior to the event. Which helped with planning his surprise entrance. He read stories and...”

Santa MikeEllis

5.0 (4)
11 Verified bookings

  • Martinsburg, WV
  • Santa Claus / Holiday Party Entertainment
  • 22 miles from Winchester
  • Starts at $175 per hour

Derrick J. said “Santa Mike was everything we needed him to be and some... We are extremely grateful and would like to use him for any Santa events going forward”

Joe Whitney Jazz

5.0 (3)
4 Verified bookings

  • Purcellville, VA
  • Jazz Band / Holiday Party Entertainment
  • 24 miles from Winchester
  • Contact for pricing

Jessica B. said “J2B (Joe Jazz Band) was just what we wanted for our 320 person event! Some nice jazz for everyone to focus on and enjoy...or to have something nice in the background while in conversation. We will...”

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

5.0 (4)
7 Verified bookings

  • Ashburn, VA
  • Magician / Holiday Party 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.”

Santa’s Helper Rickalaus

5.0 (1)
2 Verified bookings

  • Ashburn, VA
  • Santa Claus / Holiday Party Entertainment
  • 38 miles from Winchester
  • Contact for pricing

Alex A. said “Santa's Helper Rickalaus has joined us for the last few years at our client holiday party and he is absolutely wonderful! Santa Rick is communicative, kind, professionally, reasonably-priced, and...”

Refined Mixology LLC

1 Verified booking

  • Gainesville, VA
  • Bartender / Holiday Party Entertainment
  • 40 miles from Winchester
  • Contact for pricing

Refined Mixology offers professional mobile bartending for weddings, private parties, and corporate events. I create high-quality cocktails and mocktails with a...

Start getting quotes

Tell us what you need and we’ll match you with the best options for your event. Receive messages and free, no-obligation quotes from interested talent right away.

Get quick quotes

Book with confidence

When you hire a Winchester Holiday Party Entertainer through GigSalad, you’re backed by our Worry-Free Guarantee. From secure payments to reliable support, we’ve got your back.

Learn more

About booking Holiday Party Entertainment in Winchester, VA

The holidays offer special opportunities to create joy and connection with people you care about the most, and the right entertainment can make your celebration truly shine. From Christmas carolers setting a festive mood to Santas delighting children or DJs keeping the dance floor busy, professional entertainers bring the magic that makes a party memorable. Whether you’re planning a large corporate holiday party or a cozy family Christmas party, you can find the right performer to help you create unforgettable moments.

The cost of hiring holiday party entertainers in Winchester, Virginia will vary depending on the type of holiday entertainment, their experience, and the length of the performance. A short Santa visit at your family Christmas party will cost less than a live band performing at a holiday corporate event. Contact the local entertainers above to discuss your event details and receive a customized quote.

As you search for Winchester holiday party entertainers, view their profiles to read about their services, browse photos, and watch promotional videos. Then, check out reviews from past clients to see what it would be like to work with them. When requesting a quote, include key details like the venue, audience size, expected performance time, and event goals to ensure you receive the most accurate pricing.

Once you find the holiday act you want to hire, finalize the booking on GigSalad. Our full-service platform makes it easy to book holiday party entertainers. You can message the performers, 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 relax and let the holiday magic unfold!

Holiday Party Entertainment serving the Winchester, VA area

These Holiday Party 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.