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365 Holiday Party Entertainers serving Winston-Salem, NC

Featured

MJ Santa

5.0 (31)
Top Performer
59 Verified bookings

  • Winston-Salem, NC
  • Santa Claus / Holiday Party Entertainment
  • Starts at $225 per hour

Jill W. said “MJ was a great Santa for us at our Hometown Christmas event held in Elon. He was great at communication, looked the part and was flexible to our needs I recommend him for community events!”
Featured

Santa Larry

5.0 (8)
Top Performer
10 Verified bookings

  • Winston-Salem, NC
  • Santa Claus / Holiday Party Entertainment
  • Starts at $200

Kala R. said “Santa Larry is truly the ultimate Santa Claus. We hired him for a residential event, and he was nothing short of magical and a breath of fresh air. He genuinely brought the Christmas spirit to life...”
Featured

Ovations Big Band

5.0 (1)
6 Verified bookings

  • Greensboro, NC
  • Jazz Band / Holiday Party Entertainment
  • 25 miles from Winston-Salem
  • $1,000 – $10,000 per event

Bonnie S. said “Very professional to work with and attention to details. Had a stage layout drawing from them and a face to face meeting to discuss all details. They were perfect for the 35th anniversary celebration...”

Champlain Music

5.0 (9)
Top Performer
11 Verified bookings

  • Greensboro, NC
  • Classical Ensemble / Holiday Party Entertainment
  • 25 miles from Winston-Salem
  • $400 – $1,500 per event

Karen S. said “The folks at Champlain Music were wonderful to work with. They coordinated the music our daughter wanted at her wedding ceremony and she was very pleased with the results. They listened to what...”

Prelude Productions

5.0 (11)
20 Verified bookings

  • Clemmons, NC
  • Jazz Band / Holiday Party Entertainment
  • 9 miles from Winston-Salem
  • Starts at $500

Alyssa A. said “We had a trio play at our annual wine tasting event, and the band was amazing! All of our guests were raving about them. Highly, highly recommend.”

Santa PapaJoe

5.0 (6)
19 Verified bookings

  • Kernersville, NC
  • Santa Claus / Holiday Party Entertainment
  • 10 miles from Winston-Salem
  • Contact for pricing

Zachery said “Shower up on time, and ready! Great with kids of all ages ”

Santa Kelly

1 Verified booking

  • Salisbury, NC
  • Santa Claus / Holiday Party Entertainment
  • 32 miles from Winston-Salem
  • Starts at $150 per hour

Hi, I’m Santa Kelly, a professional, real-bearded Santa with something a little special—an elf-like ear! I tell children it’s one of the reasons I was chosen to...

Matt Novak

5.0 (18)
Top Performer
16 Verified bookings

  • Greensboro, NC
  • Magician / Holiday Party Entertainment
  • 25 miles from Winston-Salem
  • Contact for pricing

Lisa R. said “Matt was amazing! He came to my son's 18th birthday party and took the time to mingle with guests of all ages. He was professional, engaging, and incredibly talented. Everyone was impressed by his...”

Chrishawn Darby Trio

5.0 (1)
Top Performer
2 Verified bookings

  • Greensboro, NC
  • Jazz Band / Holiday Party Entertainment
  • 25 miles from Winston-Salem
  • Starts at $500

Michelle J. said “My team wanted to create a jazz club atmosphere for our residents to enjoy an evening of live music, and the Chrishawn Darby Trio delivered! They brought the smooth jazz, and our residents loved every...”

Santa John

5.0 (2)
Top Performer
5 Verified bookings

  • Asheboro, NC
  • Santa Claus / Holiday Party Entertainment
  • 36 miles from Winston-Salem
  • Contact for pricing

Marie M. N. said “Santa John was perfect! He delighted the children , was warm and friendly. Even our shy little one sat in his lap. Definitely recommend . ”

Santa Eric

4.98 (48)
Top Performer
92 Verified bookings

  • Reidsville, NC
  • Santa Claus / Holiday Party Entertainment
  • 37 miles from Winston-Salem
  • Starts at $125

Liz R. said “Santa Eric has come to our annual class party for the past 4 years. We all love sharing our "heart's desire" with him. BTW, everyone in the class is now 73-74 years old. We've been friends since...”

Ed McCarty's Characters

5.0 (24)
Top Performer
46 Verified bookings

  • Gibsonville, NC
  • Santa Claus / Holiday Party Entertainment
  • 39 miles from Winston-Salem
  • Starts at $75

Kait E. said “Santa Ed was so so great! He was patient and silly and so fun - all kids and parents raved about how much better he was than the Santa's we've used before. Would definitely recommend him and hope to...”

Tin Roof Cats

5.0 (1)
1 Verified booking

  • Winston-Salem, NC
  • Jazz Band / Holiday Party Entertainment
  • Contact for pricing

Leslie B. said “The Epiphany Project exceeded all expectations for our August 24, 2019 wedding reception! Phenomenal set-list and outstanding sound. They knew when to turn it up and when to slow it down. Their...”

Santa Claus Neil

5.0 (9)
9 Verified bookings

  • Winston-Salem, NC
  • Santa Claus / Holiday Party Entertainment
  • Starts at $75

Troy B. said “Neil was without a doubt one of the best Santas I've ever had the pleasure of working with. He was perfectly on time (despite having a setback out of his control earlier in the day), gave us choices...”

The Parlor Magic Experience

5.0 (5)
1 Verified booking

  • Winston-Salem, NC
  • Magician / Holiday Party Entertainment
  • $2,500 – $3,500 per event

Ryan J. said “Lyndy’s one-of-a-kind mixture of comedy and magic resulted in laughter and enjoyment by our many guests. Reviews from attendees were glowingly positive. A fun treat for all ages!”

Around The Rim Bartending

5.0 (2)
1 Verified booking

  • Winston-Salem, NC
  • Bartender / Holiday Party Entertainment
  • $500 – $1,000 per event

Cody K. said “My wife and I could not have been happier with booking Around the Rim Bartending for our wedding. Sharice was very responsive with everything that came to planning before the big day, was very easy to...”

Freeport

5.0 (4)
7 Verified bookings

  • Winston-Salem, NC
  • Jazz Band / Holiday Party Entertainment
  • Contact for pricing

Lori T. said “I cannot say enough good things about my experience with these guys! I actually had the smaller version of the band called Jazzen. They were perfect for the intimate space and party I had (surprise...”

Seasons Best Carolers

5.0 (1)
4 Verified bookings

  • Winston-Salem, NC
  • Christmas Carolers / Holiday Party Entertainment
  • Starts at $350

Jim H. said “We would certainly use the group again and would recommend them to others.”

Piedmont Santa

5.0 (2)
4 Verified bookings

  • Winston-Salem, NC
  • Santa Claus / Holiday Party Entertainment
  • Starts at $150

Jenny I. said “We were very pleased with Piedmont Santa's visit this past weekend. He was great with all the kids and looked authentic!”

Santa Kurt

5.0 (6)
6 Verified bookings

  • Winston-Salem, NC
  • Santa Claus / Holiday Party Entertainment
  • Contact for pricing

Amy W. said “Santa Kurt was a wonderful addition to our company Christmas party! He was very interactive with all the adults and children! Great communication. ”

Owen Wood Piano

5.0 (5)
8 Verified bookings

  • Winston-Salem, NC
  • Pianist / Holiday Party Entertainment
  • Contact for pricing

Eric G. said “I can highly recommend Owen Wood. He served as our guest musician and vocalist at our church this past Sunday and our members truly enjoyed him. He arrived early to set up. He was great on the...”

Piano magic

2 Verified bookings

  • Winston-Salem, NC
  • Pianist / Holiday Party Entertainment
  • Contact for pricing

I enjoy entertaining audiences with the piano. My repertoire includes ragtime standards, spirituals, showtunes, Holiday favorites, and easy-listening music. I...

Justin Nelson Jazz

5.0 (30)
41 Verified bookings

  • Winston-Salem, NC
  • Pianist / Holiday Party Entertainment
  • Starts at $150

Sherry V. said “Justin provided music for a holiday-themed rehearsal dinner for our son’s wedding. He was pleasant and very versatile. When the group was ready for some music that was more than in the background,...”

Santa Don

5.0 (18)
30 Verified bookings

  • Winston-Salem, NC
  • Santa Claus / Holiday Party Entertainment
  • Contact for pricing

Miryam B. said “This is the second year Mr. Don has come to our Christmas event. The kids love it and the pictures come out great! He is easy to communicate with and very nice overall. Thank you for making our...”

Carolers of Christmas Past

5.0 (11)
22 Verified bookings

  • Clemmons, NC
  • Christmas Carolers / Holiday Party Entertainment
  • 9 miles from Winston-Salem
  • Contact for pricing

James S. said “For folks unable to see their grandchildren at Christmas, Carolers of Christmas Past brought some Christmas cheer to their front door. Their performance was awesome !”

Idaho Magician Josh Clemente

5.0 (3)
3 Verified bookings

  • Clemmons, NC
  • Magician / Holiday Party Entertainment
  • 9 miles from Winston-Salem
  • Starts at $285

Kyley J. said “Josh provided entertainment for a large group for hours. He captivated all ages with his magic. He was great!”

Santa Barry W

4.91 (22)
42 Verified bookings

  • Germanton, NC
  • Santa Claus / Holiday Party Entertainment
  • 11 miles from Winston-Salem
  • $110 – $125 per hour

Tiffany M. said “The kids loved meeting Santa! He was cheerful, funny, captivating, and kids and adults had a great time! We spoke on the phone before event and he was very thorough in what to expect. Highly recommend...”

Captain Jim & Crew Entertainment Services

4.98 (7)
6 Verified bookings

  • Colfax, NC
  • Magician / Holiday Party Entertainment
  • 13 miles from Winston-Salem
  • Contact for pricing

Rachael S. said “We had Jim and his assistant Louisa at our Wizards and Wands (Harry Potter) themed event. Jim dressed as a wizard, added Harry Potter quotes and sayings to his act, and became a part of our theme, not...”

Signature Sips NC

1 Verified booking

  • High Point, NC
  • Bartender / Holiday Party Entertainment
  • 17 miles from Winston-Salem
  • Starts at $150

Mobile bartending service --Licensed and insured certified. We'll bring our signature libations in conjunction with your vision for your event. The...

High Point Santa Claus

4.99 (19)
1 Verified booking

  • High Point, NC
  • Santa Claus / Holiday Party Entertainment
  • 17 miles from Winston-Salem
  • Starts at $250

Kristin T. said “Santa Cliff was so awesome! He really makes you believe in Santa Claus!”

Abigail Lockhart Piano

4.93 (13)
28 Verified bookings

  • High Point, NC
  • Pianist / Holiday Party Entertainment
  • 17 miles from Winston-Salem
  • $60 – $100 per hour

Chandler M. said “Abigail came in and played for our senior living community's happy hour event. She was pinch-hitting for our regular players, which can be challenging because our members can be particular about their...”

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About booking Holiday Party Entertainment in Winston-Salem, NC

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 Winston-Salem, North Carolina 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 Winston-Salem 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 Winston-Salem, NC area

These Holiday Party Entertainment serve the wider Winston-Salem and Forsyth county area and travel to Walkertown, Pfafftown, Bethania, Wallburg, Clemmons, Kernersville, Lewisville, Rural Hall, Germanton, Tobaccoville, Bermuda Run, Colfax, Welcome, Belews Creek, King, Advance, Walnut Cove, Oak Ridge, High Point, East Bend, Thomasville, Stokesdale, Jamestown, Pine Hall, Pinnacle, Lexington, McCain, Archdale, Trinity, and Summerfield.