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372 Holiday Party Entertainers serving Pickering, ON

Featured

Santa Jamie

5.0 (1)
Top Performer
3 Verified bookings

  • Oshawa, ON
  • Santa Claus / Holiday Party Entertainment
  • 12 miles from Pickering
  • Starts at $250

Heather R. said “Santa Jamie came to our gymnastics class for children with autism. He was absolutely incredible! He took the time to get to know each child. When a child was hesitant to come see him he took their...”
Featured

Heather's Hospitality

5.0 (3)
Top Performer
2 Verified bookings

  • Toronto, ON
  • Waitstaff / Holiday Party Entertainment
  • 20 miles from Pickering
  • Starts at $18 per hour

Catherine C. said “Heather was professional and prompt. She was very attentive and made sure my guests were well taken care of. Would definitely book her again! ”
Featured

Rosemary Reid - Toronto's Female Magician

4.95 (58)
Top Performer
94 Verified bookings

  • Toronto, ON
  • Magician / Holiday Party Entertainment
  • 20 miles from Pickering
  • Contact for pricing

Gen S. said “We booked Rosemary for a large client event and she was dressed in a stunning dress, captivating our clients with her magic. It was a pleasure working with her and I'd re-book her if we have the...”
Featured

Alexander Solo Piano

4.95 (48)
Top Performer
85 Verified bookings

  • Toronto, ON
  • Pianist / Holiday Party Entertainment
  • 20 miles from Pickering
  • Starts at $150

Deirdre D. said “Alexander performed at a Memorial Service for my brother. I trusted him to choose the gospel selections and Alexander did not disappoint! He was professional and prepared. He delivered as promised...”
Featured

Robert Chan Magic

5.0 (7)
Top Performer
8 Verified bookings

  • Toronto, ON
  • Magician / Holiday Party Entertainment
  • 20 miles from Pickering
  • Contact for pricing

Inger H. said “We were a small group of 14. All participated and had a great time with Robert! Would definitely recommend him”
Featured

Fluid Event Services

5.0 (1)
Top Performer
2 Verified bookings

  • Toronto, ON
  • Bartender / Holiday Party Entertainment
  • 20 miles from Pickering
  • $40 – $10,000 per hour

Bedston M. said “For many years, Carla has helped us doing events and bartending our social gatherings. Mostly for family and friends. Her homemade Hibiscus Drink is a favourite and we would recommend her and her team...”
Featured

Private Pour Co.

5.0 (18)
Top Performer
19 Verified bookings

  • Toronto, ON
  • Bartender / Holiday Party Entertainment
  • 20 miles from Pickering
  • Contact for pricing

Sharon H. said “We had a fantastic experience with Will and Parmida at our cocktail party. They were friendly, professional and engaging and really helped make our 1930's cocktail evening a success. Their flexibility...”
Featured

IllusioniStorm

5.0 (16)
Top Performer
24 Verified bookings

  • Toronto, ON
  • Magician / Holiday Party Entertainment
  • 20 miles from Pickering
  • Starts at $400

Sydney B. said “Storm was amazing at every step of the process. Very kind, thoughtful, easy to work with, and with tricks that kept everyone guessing, we would absolutely recommend him for any occasion. ”
Featured

Ken Margoe - Illusionist

5.0 (2)
Top Performer
1 Verified booking

  • Toronto, ON
  • Magician / Holiday Party Entertainment
  • 20 miles from Pickering
  • $500 – $5,000 per event

Marcus C. said “Our magician made my birthday party unforgettable with card tricks that had the whole room leaning in and second-guessing everything we saw. His mentalist segment was the highlight – he read people...”
Featured

V & G Entertainment

5.0 (36)
Top Performer
77 Verified bookings

  • Toronto, ON
  • Classical Ensemble / Holiday Party Entertainment
  • 20 miles from Pickering
  • Contact for pricing

John S. said “It was really nice music performance”
Featured

Santa Dave Hastings

5.0 (10)
Top Performer
14 Verified bookings

  • Newmarket, ON
  • Santa Claus / Holiday Party Entertainment
  • 24 miles from Pickering
  • Starts at $300 per hour

Christina T. said “Santa Dave was incredible! He was wonderful, easy to work with, and so jolly! We got so many amazing complements on him being such an authentic Santa. We will be booking again for sure! ”
Featured

Sergey Krutik Music

5.0 (5)
10 Verified bookings

  • Markham, ON
  • Pianist / Holiday Party Entertainment
  • 13 miles from Pickering
  • Contact for pricing

Lori C. said “Played beautifully all night ... thank you so much for helping to make our event so special!!”
Featured

Adam Swaye

5.0 (3)
3 Verified bookings

  • Toronto, ON
  • Magician / Holiday Party Entertainment
  • 20 miles from Pickering
  • Contact for pricing

Gabriela G. said “Adam was excellent during the time he spent with us, interacting with all the guests, and everyone was impressed by his show around and great personality! ”
Featured

Santa Real Beard

4.87 (31)
64 Verified bookings

  • Toronto, ON
  • Santa Claus / Holiday Party Entertainment
  • 20 miles from Pickering
  • Contact for pricing

Andre C. said “Santa was incredible, very responsible for all our messages and very well spoken with the kids. He had answers for all the kids questions. The whole family loved him! I would for sure book him again.”
Featured

The Kensie Jazz and Dance Band

5.0 (53)
20 Verified bookings

  • Toronto, ON
  • Jazz Band / Holiday Party Entertainment
  • 20 miles from Pickering
  • Starts at $875

Roxanne M. said “The musician was superbly talented - great musician and vocalist. Highly recommended!!!”
Featured

The Tavares Jazz Band

5.0 (26)
37 Verified bookings

  • Toronto, ON
  • Jazz Band / Holiday Party Entertainment
  • 20 miles from Pickering
  • Contact for pricing

Elric A. said “Would give them 6 stars if it was possible. The Tavares Jazz Band performed at our wedding and it was an absolute hit! The music was amazing and created the exact atmosphere we were looking for. All...”
Featured

Roman Royss

5.0 (1)
3 Verified bookings

  • Toronto, ON
  • Magician / Holiday Party Entertainment
  • 20 miles from Pickering
  • Contact for pricing

Ahmed R. said “Roman was a great act for our corporate client event. He engaged all the people in the audience, was really easy to work with and was on time and committed. Highly recommend him. As a result we...”
Featured

The Sean Stanley Trio

4.90 (20)
30 Verified bookings

  • Toronto, ON
  • Jazz Band / Holiday Party Entertainment
  • 20 miles from Pickering
  • $400 – $2,000 per event

Tricia G. said “Sean and Kyle were wonderful to work with! They played the perfect sound for our event, and arrived on time with everything needed to put on a great show. They made all the difference! I look...”
Featured

  • Toronto, ON
  • Magician / Holiday Party Entertainment
  • 20 miles from Pickering
  • $350 – $3,500 per event

Mary G. said “Gambit Magician was very accommodating with the types of magic he did - children and family friendly. He was very personable and kind to the tenants and staff of our YWCA Toronto program. Thanks for...”
Featured

Tiffany Jazz Trio

5.0 (22)
3 Verified bookings

  • Toronto, ON
  • Jazz Band / Holiday Party Entertainment
  • 20 miles from Pickering
  • $500 – $2,500 per event

Rachel M. said “We had the pleasure of enjoying a lovely performance by the Tiffany Hanus Jazz Trio in honour of my mother's 60th Birthday celebration. Tiffany was very easy to work with, and it was such a treat to...”
Featured

Mega Magic- Magician Mike D'Urzo

5.0 (23)
23 Verified bookings

  • Toronto, ON
  • Magician / Holiday Party Entertainment
  • 20 miles from Pickering
  • Contact for pricing

Graham W. said “Mike was a great entertainer and showman who greatly elevated our event!”
Featured

Christmas Past

5.0 (6)
18 Verified bookings

  • Etobicoke, ON
  • Santa Claus / Holiday Party Entertainment
  • 26 miles from Pickering
  • Starts at $275

Marie M. said “Santa Sampson was just phenomenal! Great with the students, families, and staff... He engaged with the kids and was truly magical. Thank you so much! ”
Featured

Louis Pettinelli Entertainment

4.92 (70)
249 Verified bookings

  • Mississauga, ON
  • Jazz Band / Holiday Party Entertainment
  • 33 miles from Pickering
  • Starts at $300

Alayna B. said “We hired Louis Pettinelli Entertainment for a trio including a violin, piano, and cello for our wedding reception and they did such an amazing job! They really made the evening so special. They played...”
Featured

  • Toronto, ON
  • Magician / Holiday Party Entertainment
  • 20 miles from Pickering
  • Starts at $2,000

Ashley H. said “Ben was absolutely FANTASTIC. We hosted a corporate event at Terroni on Adelaide in Toronto. During the planning process, Ben responded quickly, asked and answered any questions he or we had, and...”
Featured

  • York, ON
  • Bartender / Holiday Party Entertainment
  • 21 miles from Pickering
  • Contact for pricing

We specialize in delivering premier hospitality services designed to enhance both corporate functions and private celebrations. Our dedicated team is...
Featured

  • Mississauga, ON
  • Magician / Holiday Party Entertainment
  • 33 miles from Pickering
  • $385 – $10,000 per event

Patrick S. said “This guy is good! We had other magicians perform at our event but Roberto topped them all. Hire him!”

Magic Dmitry

5.0 (8)
Top Performer
20 Verified bookings

  • Woodbridge, ON
  • Magician / Holiday Party Entertainment
  • 26 miles from Pickering
  • $300 – $750 per event

Jamie M. said “Magic Dmitry was so wonderful! The tricks were amazing, he included all of my guests, and he was super communicative throughout the process. Everyone enjoyed the show, and I would highly recommend him...”

  • Toronto, ON
  • Jazz Band / Holiday Party Entertainment
  • 20 miles from Pickering
  • Contact for pricing

If you need a little vintage flavour at your event, look no further than The Nightbird Band, who will effortlessly transport you back to simpler times, when...

Ron Martin Magician and Illusionist

4.97 (12)
Top Performer
12 Verified bookings

  • Brampton, ON
  • Magician / Holiday Party Entertainment
  • 35 miles from Pickering
  • $400 per event

Kelley C. said “Ron was great fun for all, very personal and professional. Amazed us with his magic & Illusions. Would 💯 recommend Ron!!”

Tanya Lyn Events

4.97 (23)
Top Performer
41 Verified bookings

  • Whitby, ON
  • Bartender / Holiday Party Entertainment
  • 8 miles from Pickering
  • Starts at $300

Vanessa J. said “All my guest commented on how nice and helpful the bartender was, I'm especially grateful for how well she went with the flow of the day. And she gave me a new drink recipe I'm still enjoying. Thank...”

Raise The Bar Co.

5.0 (15)
Top Performer
17 Verified bookings

  • Toronto, ON
  • Bartender / Holiday Party Entertainment
  • 20 miles from Pickering
  • $50 per hour

Natasha A. said “I had a great experience with Pamela this weekend! She was professional, prompt, and loved by the whole party. She made everything run so smoothly, and I will certainly be using them again for my next...”

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About booking Holiday Party Entertainment in Pickering, ON

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 Pickering, Ontario 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 Pickering 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 Pickering, ON area

These Holiday Party Entertainment serve the wider Pickering area and travel to Dunbarton, Rosebank Station, Ajax, Whitevale, Port Union, Brougham, Greenwood, West Hill, Locust Hill, Whitby, Scarborough, Scarborough Township, Claremont, Agincourt, Brooklin, Brimley, Unionville, Scarborough Junction, Oshawa, Newtonville, Stouffville, Whitchurch-stouffville, Ashburn, Markham, Banbury-Don Mills, Don Mills, Myrtle Station, Goodwood, Courtice, and Gormley.