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410 Holiday Party Entertainers serving Middletown, NY

Featured

Christopher James Talio

5.0 (6)
Top Performer
4 Verified bookings

  • Cortlandt Manor, NY
  • Jazz Band / Holiday Party Entertainment
  • 31 miles from Middletown
  • $400 – $6,000 per event

Margot A. said “Most important - was an excellent musical experience that guests raved about. In addition, was incredibly professional and prepared even thru a bit of chaos on our end. Highly recommend!”
Featured

Close-Up Magic Of Marco

5.0 (38)
Top Performer
39 Verified bookings

  • Rockaway, NJ
  • Magician / Holiday Party Entertainment
  • 38 miles from Middletown
  • $500 – $3,000 per event

Alexandra M. said “We are absolutely happy with our choice of Magic of Marco! Best bachelorette decision we made. Don’t even hesitate, pick Marco!”
Featured

Farrel Hutchinson Music

4.93 (37)
Top Performer
13 Verified bookings

  • Dover, NJ
  • Pianist / Holiday Party Entertainment
  • 40 miles from Middletown
  • Contact for pricing

Isss E. said “He did exactly what I envisioned, set up was quick and simple, he was very professional and an amazing pianist. Highly recommend! He made my dream ceremony come true!”
Featured

The Music Boutique

5.0 (88)
67 Verified bookings

  • Cornwall, NY
  • Pianist / Holiday Party Entertainment
  • 20 miles from Middletown
  • Contact for pricing

Bernadette M. said “The music boutique was excellent they played classical music for my ceremony and modern music for my cocktail hour it was perfect.”
Featured

Richard Devens

4.88 (24)
53 Verified bookings

  • Poughkeepsie, NY
  • Pianist / Holiday Party Entertainment
  • 31 miles from Middletown
  • Contact for pricing

Jason K. said “Richard was a pleasure to work with and added a wonderful backdrop to our company holiday party. I would use him again without hesitation.”
Featured

Springlight Entertainment

5.0 (43)
82 Verified bookings

  • Fair Lawn, NJ
  • Jazz Band / Holiday Party Entertainment
  • 38 miles from Middletown
  • $600 – $7,000 per event

Nancy L. said “We had Pasha on the trumpet, and Arthur on the guitar, for a three hour gig. They were both wonderful! They arrived on time, they were neat, polite, and professional. They played for three hours and...”

City Winds Flute and Harp Duo

1 Verified booking

  • Boonton, NJ
  • Classical Ensemble / Holiday Party Entertainment
  • 37 miles from Middletown
  • Starts at $150

City Winds Trio and Harp Duo is an established group that has been adding great music to events for the past several years. City Winds Trio has performed...

Summertime Santa

5.0 (9)
Top Performer
9 Verified bookings

  • Oak Ridge, NJ
  • Santa Claus / Holiday Party Entertainment
  • 28 miles from Middletown
  • $150 – $500 per event

Nicol A. said “Such a great Santa! He engages with all ages. My family enjoyed it! ”

Santa Frank

5.0 (14)
Top Performer
27 Verified bookings

  • Hopatcong, NJ
  • Santa Claus / Holiday Party Entertainment
  • 38 miles from Middletown
  • Contact for pricing

Yolenny N. said “Santa Frank was puntual and very professional. All the kids and adults loved him. Great sense of humor. ”

The Alex Slomka Group

5.0 (1)
Top Performer
1 Verified booking

  • Pleasantville, NY
  • Jazz Band / Holiday Party Entertainment
  • 39 miles from Middletown
  • $200 – $3,000 per event

Jean P. P. said “Alex and his band killed it at our engagement party. The sound and the quality of the pieces they played was on point. Love them and super gratefull for their amazing profesionality. ”

Experienced Bartender

5.0 (2)
3 Verified bookings

  • Middletown, NY
  • Bartender / Holiday Party Entertainment
  • $50 per hour

Werner P. said “Fantastic drinks, very punctual and organized, friendly and professional. Everyone at the event loved her! ”

A Plus Party Specialists LLC

5.0 (3)
1 Verified booking

  • Glenwood, NJ
  • Waitstaff / Holiday Party Entertainment
  • 14 miles from Middletown
  • Contact for pricing

Alan S. said “My Wife and I had decided to have my Mom’s 80th Birthday Party at our home. We reached out to Peggy to cater the party. All I can say is what an Amazing job Peggy and her staff did! Friendly and...”

PerfectPitch

5.0 (2)
2 Verified bookings

  • Highland Mills, NY
  • Pianist / Holiday Party Entertainment
  • 17 miles from Middletown
  • $400 – $2,000 per event

Joanne L. said “Noah created wonderful atmosphere. Highly recommended.”

Joe Vincent Tranchina

5.0 (1)
1 Verified booking

  • Greenwood Lake, NY
  • Jazz Band / Holiday Party Entertainment
  • 17 miles from Middletown
  • Starts at $250

Rosie G. said “Joe and his band were great, we loved the Jazz music they provided for our family event of 130 guests. He arrived nice and early and set up ahead of the event, was very communicative and hima nd his...”

Santa Ron

5.0 (8)
12 Verified bookings

  • Sussex, NJ
  • Santa Claus / Holiday Party Entertainment
  • 19 miles from Middletown
  • Contact for pricing

Kelly B. said “Santa Ron is awesome! He is so great with the kids. This is our second year having him at our family Christmas party.”

Neil Alexander

5.0 (1)
1 Verified booking

  • Newburgh, NY
  • Jazz Band / Holiday Party Entertainment
  • 22 miles from Middletown
  • Contact for pricing

Reisa A. said “Neil is a truly first class keyboard player. He is extremely professional and a wonderful person to work with. I am amazed at his level of talent! He is a chameleon and a wizard on the keyboard!!! ...”

East Coast Jazz Trio

5.0 (1)
1 Verified booking

  • Beacon, NY
  • Jazz Band / Holiday Party Entertainment
  • 24 miles from Middletown
  • Contact for pricing

Cameron M. said “Mike did an excellent job communicating ahead of time, organizing the band, asking about requests, and learning the timeline for our wedding. On the day of, the trio showed up on time, sounded...”

Real Beard Santa John

3 Verified bookings

  • Stockholm, NJ
  • Santa Claus / Holiday Party Entertainment
  • 25 miles from Middletown
  • Contact for pricing

Real beard Santa In home visits as well as company and corporate parties over 48 years experience

Santa Malcolm

5.0 (10)
23 Verified bookings

  • Ringwood, NJ
  • Santa Claus / Holiday Party Entertainment
  • 25 miles from Middletown
  • $200 – $1,500 per event

Michael B. said “Santa Malcom was incredible! Far exceeded my expectations - we hoped for some cute pictures, ended up having that plus amazing singing and story telling! Santa Malcolm had some of the older kids leave...”

John Bernstein-Pianist

5.0 (1)
2 Verified bookings

  • Grahamsville, NY
  • Pianist / Holiday Party Entertainment
  • 29 miles from Middletown
  • Starts at $75 per hour

Brendan D. said “Incredible musician. Provided exactly the ambiance I wanted for my cocktail hour. Would highly reccomend”

Cassotis Music LLC

1 Verified booking

  • Mahwah, NJ
  • Pianist / Holiday Party Entertainment
  • 29 miles from Middletown
  • Starts at $420

Zoe is a pianist, whose solo piano performances range across musical styles, including Renaissance, Baroque, Romantic, Impressionism, Classical Jazz, and Stride...

Santa Jerry

5.0 (3)
7 Verified bookings

  • Mahwah, NJ
  • Santa Claus / Holiday Party Entertainment
  • 29 miles from Middletown
  • Starts at $75

Holly F. said “Santa Jerry was at our extended family party and was just captivating for the kids. He read to them and spent time with each of them as he handed out gifts and chatted with them. Great experience and...”

The Real NY Santa

5.0 (3)
14 Verified bookings

  • Highland, NY
  • Santa Claus / Holiday Party Entertainment
  • 31 miles from Middletown
  • Contact for pricing

Janet C. said “The Real NY Santa was absolutely great! Professional, courteous and kind to the children. He looks the part and everyone loved him. I highly recommend!”

Magic Variety Show by Steve J

5.0 (1)
3 Verified bookings

  • Poughkeepsie, NY
  • Magician / Holiday Party Entertainment
  • 31 miles from Middletown
  • Contact for pricing

Stephanie said “Steve was terrific! The kids ALL had a blast, which is no small feat for an audience encompassing pre-K through 12th grade! The faculty and staff loved it as well, and left talking about his great...”

Blake Rowe Music

5.0 (3)
4 Verified bookings

  • Croton On Hudson, NY
  • Pianist / Holiday Party Entertainment
  • 32 miles from Middletown
  • $300 – $500 per event

Matthew W. said “Blake was punctual, professional, and played great at my wedding. Thanks for contributing to our special day!”

Santa Ken

5.0 (2)
2 Verified bookings

  • Valley Cottage, NY
  • Santa Claus / Holiday Party Entertainment
  • 33 miles from Middletown
  • Contact for pricing

Maya . A. D. B. M. said “Very genuine, patient, kind with kids and looks like the real one! ”

Cabana-Santa LLC

5.0 (20)
34 Verified bookings

  • Andover, NJ
  • Santa Claus / Holiday Party Entertainment
  • 36 miles from Middletown
  • Contact for pricing

Michele S. said “Cabana Santa was awesome. He interacted with everyone. The kids loved him. ”

Mr & Mrs Santa Claus Paul

5.0 (19)
32 Verified bookings

  • Haledon, NJ
  • Santa Claus / Holiday Party Entertainment
  • 37 miles from Middletown
  • Contact for pricing

Jannett H. said “Santa and Mrs Santa Claus were outstanding during a recent photoshoot I did with them for my children. Loved how understanding they were. Santa interacted well with the children, especially in working...”

Santa Rick

5.0 (11)
28 Verified bookings

  • Boonton, NJ
  • Santa Claus / Holiday Party Entertainment
  • 37 miles from Middletown
  • Contact for pricing

Antonio E. said “Great job ”

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About booking Holiday Party Entertainment in Middletown, NY

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 Middletown, New York 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 Middletown 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 Middletown, NY area

These Holiday Party Entertainment serve the wider Middletown and Orange county area and travel to New Hampton, Howells, Wallkill, Slate Hill, Circleville, Goshen, Otisville, Johnson, Bullville, Bloomingburg, Westbrookville, Campbell Hall, Florida, Cuddebackville, Wurtsboro, Westtown, Thompson Ridge, Chester, Burlingham, Pine Island, Maybrook, Huguenot, Montgomery, Sugar Loaf, Blooming Grove, Rock Tavern, Summitville, Unionville, Pine Bush, and Walker Valley.

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