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350 Holiday Party Entertainers serving Middletown, CT

Featured

D'Amico Entertaintainment

5.0 (88)
Top Performer
45 Verified bookings

  • West Hartford, CT
  • Jazz Band / Holiday Party Entertainment
  • 15 miles from Middletown
  • Contact for pricing

Matthew G. said “We hired D'amico Entertainment for our grand opening event, and they were absolutely excellent. Performing a four piece jazz ensemble in a cavernous car dealership service department is no easy trick,...”
Featured

Santa Mark CT

5.0 (5)
Top Performer
9 Verified bookings

  • Woodbridge, CT
  • Santa Claus / Holiday Party Entertainment
  • 24 miles from Middletown
  • $175 – $400 per hour

Tamara M. said “Santa Mark was the PERFECT addition to our holiday party. He brought true Christmas Magic. I wasn’t sure how the staff would react to Santa (all adults) but the moment he walked in (he was the...”
Featured

Santa Scott CT

5.0 (7)
Top Performer
10 Verified bookings

  • Oakdale, CT
  • Santa Claus / Holiday Party Entertainment
  • 26 miles from Middletown
  • Contact for pricing

Staci G. said “We were so grateful to have Santa volunteer his time to visit our integrated preschool program. He was wonderful with all of our children and showed a great understanding of their different needs...”
Featured

Gabriel Landstedt, Pianist

5.0 (3)
Top Performer
4 Verified bookings

  • Norwich, CT
  • Pianist / Holiday Party Entertainment
  • 30 miles from Middletown
  • Contact for pricing

Susan C. said “We held a Bridal Shower at The Space in Westerly. Gabriel pleasantly provided some lovely background music on his piano! The crowd was very pleased to have this added experience while enjoying good...”
Featured

Santa Rich

4.91 (13)
Top Performer
33 Verified bookings

  • Milford, CT
  • Santa Claus / Holiday Party Entertainment
  • 31 miles from Middletown
  • Starts at $150 per hour

Michael T. said “Santa Rich is an incredible Santa. He is a great communicator for business. He brings smiles and sentimental moment(s) to all that encounter him. At our Christmas in July event he even gave away Santa...”
Featured

Santa Bubba

5.0 (25)
Top Performer
40 Verified bookings

  • Ashford, CT
  • Santa Claus / Holiday Party Entertainment
  • 35 miles from Middletown
  • $150 – $400 per event

Alysa U. said “Santa Bubba was amazing! He was so patient and kind with the kids. We had 8 kiddos ages 1-5 and they were all so happy! We would absolutely recommend him and plan to use him again in the future! ”
Featured

Santa Dan CT

5.0 (14)
Top Performer
22 Verified bookings

  • Mystic, CT
  • Santa Claus / Holiday Party Entertainment
  • 38 miles from Middletown
  • Starts at $100

Rocco S. said “Our wedding was Christmas weekend (12/22/23) and what better guest to surprise our guests with no other than Saint Nick himself! Best Santa we could have. Kids (and grownups) loved him!”
Featured

The Christmas Carolers, LLC

4.78 (14)
61 Verified bookings

  • Hartford, CT
  • Christmas Carolers / Holiday Party Entertainment
  • 14 miles from Middletown
  • Contact for pricing

Nancy R. said “The Christmas Carolers did a fabulous job at our annual Christmas luncheon. They entertained 140+ people with beautiful and festive sounds of the holiday season.”
Featured

Santa Shane

5.0 (6)
17 Verified bookings

  • Waterbury, CT
  • Santa Claus / Holiday Party Entertainment
  • 21 miles from Middletown
  • Contact for pricing

Rosa A. said “Santa Shane was amazing prompt, engaging, and fun !!”

The Santa Connection

5.0 (25)
Top Performer
43 Verified bookings

  • Hartford, CT
  • Santa Claus / Holiday Party Entertainment
  • 14 miles from Middletown
  • Contact for pricing

Sean M. said “Santa Dave is the real deal! Everyone was impressed with Santa Dave. He made each child feel special and looked incredible. We hope to have him back next year!”

Gomez & Sadlon

4.91 (14)
Top Performer
12 Verified bookings

  • Newtown, CT
  • Jazz Band / Holiday Party Entertainment
  • 35 miles from Middletown
  • $400 – $1,000 per event

Cheryl A. said “Having background music at our son’s rehearsal dinner was the best idea yet. It added such a nice atmosphere to an already special event. The music provided was varied and pleased everyone’s taste....”

Santa John

4.88 (34)
70 Verified bookings

  • Cheshire, CT
  • Santa Claus / Holiday Party Entertainment
  • 14 miles from Middletown
  • Starts at $100

Amanda C. said “Santa John was great! Prompt and professional. The kids loved him. We really appreciate him and our daughter had an amazing birthday thanks to him! ”

Shamrock Santa

2 Verified bookings

  • Hamden, CT
  • Santa Claus / Holiday Party Entertainment
  • 18 miles from Middletown
  • $200 – $350 per event

Sharing the joy of the Christmas season with the young and young at heart in the Connecticut area.

  • Hartford, CT
  • Jazz Band / Holiday Party Entertainment
  • 14 miles from Middletown
  • $500 – $5,000 per event

Celebrate your next event with the vintage charm of the Mama Train Jazz Band! Featuring rich female vocals and lively piano, we are a team of top-notch...

Connecticut Yuletide Carolers

4.90 (22)
Top Performer
41 Verified bookings

  • Guilford, CT
  • Christmas Carolers / Holiday Party Entertainment
  • 19 miles from Middletown
  • Contact for pricing

Voniettee J. said “Group was enjoyed by all the employees. They were professional and on time. The teams loved the selection of songs and participated. Such a pleasant time with all. ”

Ulterior Motif

5.0 (5)
6 Verified bookings

  • Wallingford, CT
  • Classical Ensemble / Holiday Party Entertainment
  • 12 miles from Middletown
  • Starts at $500

Stephanie C. said “Professional, punctual and insanely talented trio! There are not enough good things to say about them! Thank you thank you thank you!”

  • Hartford, CT
  • Jazz Band / Holiday Party Entertainment
  • 14 miles from Middletown
  • $500 – $2,000 per event

Rich P. said “I WILL HIRE THIS GROUP AGAIN THEY WERE PROFESSIONAL AS WELL AS INTERACTIVE WITH THE EVENT THERE MUSICAL EXPERTISE ASTOUNDED MY GUESTS”

Steve Donovan

5.0 (39)
48 Verified bookings

  • Hartford, CT
  • Pianist / Holiday Party Entertainment
  • 14 miles from Middletown
  • Contact for pricing

Lisa B. said “Steve was a lovely addition to our employee appreciation event. He's very talented and was responsive and easy to work with.”

A Joyful Note Piano

5.0 (1)
1 Verified booking

  • Hartford, CT
  • Pianist / Holiday Party Entertainment
  • 14 miles from Middletown
  • $100 – $450 per event

Antwon H. said “A job well done.”

Mibartender

5.0 (50)
76 Verified bookings

  • West Hartford, CT
  • Bartender / Holiday Party Entertainment
  • 15 miles from Middletown
  • Contact for pricing

Emily N. said “It was such a treat having Michelle here to bartend my 40th! I came up with a few signature cocktails and she arrived on time, set up well, and did a great job. Everyone at the party loved the bar!...”

Wild Wild Zest Beverage Bar

5.0 (1)
1 Verified booking

  • Manchester, CT
  • Bartender / Holiday Party Entertainment
  • 16 miles from Middletown
  • $500 – $2,500 per event

Steph H. said “Thank you for the great drinks and service! I truly appreciate your ability to pivot and make everything work when my plans suddenly changed. You're the best! I would definitely hire you again!! ”

Sexy Bartender's

4.89 (8)
9 Verified bookings

  • Bristol, CT
  • Bartender / Holiday Party Entertainment
  • 17 miles from Middletown
  • $30 – $35 per hour

Dawn M. said “Both the hosts and the guests enjoyed her very much. Very entertaining and can converse with nearly anyone. She was a great fit definitely sure to use her again in the future.”

Holly Jolly LLC

5.0 (3)
17 Verified bookings

  • Bristol, CT
  • Santa Claus / Holiday Party Entertainment
  • 17 miles from Middletown
  • Starts at $200

Elaina G. said “Santa Eric is as great as they come - with his authentic beard and mustache wonderful costume, and bells on his shoes, he added so much magic and charm to our event!”

Santa Chip

4.87 (37)
80 Verified bookings

  • Essex, CT
  • Santa Claus / Holiday Party Entertainment
  • 19 miles from Middletown
  • Contact for pricing

Nathan S. said “Santa Chip was great!”

Barbara Lewis Jazz

5.0 (2)
2 Verified bookings

  • Avon, CT
  • Jazz Band / Holiday Party Entertainment
  • 19 miles from Middletown
  • Starts at $250

Amy P. said “We booked Barbara Lewis Band for our Valentine's Day Dinner and Dance at our private business club and the members loved them! They were very professional and a pleasure to work with. I look forward...”

Sazzy Brass

5.0 (1)
1 Verified booking

  • Windsor, CT
  • Jazz Band / Holiday Party Entertainment
  • 20 miles from Middletown
  • $300 – $1,000 per event

Rachel N. said “Who knew a trombonist and trumpeter could sound like an entire jazz band? Jazzy Brass can do it with highly recognizable songs that make you want to sing along. Fly me to the moon and Moondance...”

Liquid Solutions

5.0 (2)
3 Verified bookings

  • Windsor, CT
  • Bartender / Holiday Party Entertainment
  • 20 miles from Middletown
  • Starts at $150

Kaylan T. said “Quin did an amazing job bartending our wedding. He came prepared with his own mixers, table, and ice. The drinks were fantastic and everyone loved him. Would definitely hire again for another event.”

Mr & Mrs Claus of Waterbury

5.0 (8)
11 Verified bookings

  • Waterbury, CT
  • Santa Claus / Holiday Party Entertainment
  • 21 miles from Middletown
  • $200 – $575 per event

Gail B. said “Mr. and Mrs. Claus provided a wonderful addition to our extended family Christmas party. They were obliging, warm and wonderful with our littles. We loved their outfits. This was the second time we...”

Piano / Vocalist

5.0 (3)
3 Verified bookings

  • Westbrook, CT
  • Pianist / Holiday Party Entertainment
  • 21 miles from Middletown
  • $300 – $750 per event

Patty T. said “Paul provided great music for all of our tastes. We all sang along to the Beatles, Elton John, Billy Joel and more! Paul has a great sound system as well. His iPad with all the choices of songs and...”

Mr and Mrs Santa

5.0 (7)
12 Verified bookings

  • Coventry, CT
  • Santa Claus / Holiday Party Entertainment
  • 22 miles from Middletown
  • Contact for pricing

Evi G. said “Wonderful visit from Santa and Mrs. Claus! We had a lot of fun signing songs, reading and ringing bells.”

Santa John Claus

5.0 (5)
14 Verified bookings

  • Beacon Falls, CT
  • Santa Claus / Holiday Party Entertainment
  • 23 miles from Middletown
  • Starts at $350

Wanda H. said “What a wonderful couple! Santa and Mrs. Claus did not disappoint at ALL!! What a truly magical night they made for all us (including the children)!! We look forward to having them back next year.”

Free2BeBrilliant Entertaining

5.0 (1)
1 Verified booking

  • Old Saybrook, CT
  • Bartender / Holiday Party Entertainment
  • 23 miles from Middletown
  • Starts at $240

Nichole S. said “Jackie and her team were incredibly hardworking, kind, and professional! They made my wedding enjoyable!! They followed all covid guidelines! Couldn't have picked a better group!! I strongly suggest...”

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About booking Holiday Party Entertainment in Middletown, CT

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, Connecticut 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, CT area

These Holiday Party Entertainment serve the wider Middletown and Middlesex county area and travel to Portland, Cromwell, Rockfall, Middlefield, Cobalt, Middle Haddam, East Berlin, Durham, Berlin, Rocky Hill, Higganum, Lake Pocotopaug, East Hampton, South Glastonbury, Kensington, Meriden, Haddam, New Britain, East Haddam, Wethersfield, Newington, Glastonbury, East Glastonbury, Marlborough, Moodus, Wallingford, Southington, Plantsville, Milldale, and North Westchester.

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