The 242 Best Holiday Party Entertainers for Hire in Winchester, MA

Alex K. said “Hired Kevin for a house party, and he was very professional and provided great sounding jazz music! Thanks again Kevin. -Alex”

Channing S. said “Thank you, Mike, for the incredible show! Mike performed for our corporate event of 600 people and knocked it out of the park! The crowd was engaged the…”

Kathleen M. said “Matt did an amazing job and captivated the attention of my entire 2nd grade class!”

Sarah G. said “Dan and the group were amazing. They had a great selection of music for our corporate holiday party moving from cocktail hour to dinner music. Well timed…”

Jenna R. said “Santa John and Mrs Claus were great with the kids and the adults! Definitely will be booking again next year!”

Saman M. said “Scott did a wonderful job. Most of all, Scott is very professional. Our event had a rocky start in sense of communication and lack of volunteers show…”

Dr P. S. said “We are a Boston area alumni organization. The venue we used required a licensed, professional bar tender. EES provided this effectively and at a reasonable…”

Melissa R. said “Santa was amazing !! He was so great with the kids and he is very reasonable for prices. Thank you so much for making Christmas Eve so magical.”

Patty H. said “We hired Joe for our annual Christmas dinner. He was absolutely fantastic! We enjoyed him very much. Very entertaining!”

Dan M. said “Gerry was friendly and professional. His performance exceeded expectations!”

Thomas E. N. said “Dan was simply spectacular. We had a small venue wedding and he adjusted all the music to the attitude of our guests and we found his 4 hours of delightful…”

Cheryl L. said “The Holiday Victorian Carolers made a surprise visit to my brother’s private Christmas Party in Ipswich, Massachusetts. He and the 40 guests were so surprised…”

Mega. said “Gillian is amazing! I’ll definitely be working with her again :)”

Robin H. said “I hired 3 staff workers to assist in setting up, serving and clean up for my brunch. The woman did a fabulous job and they were very professional, courteous…”

Anne L. said “Literally, SpeechLess blew me away! The horns were the highlight of the night at our company gala, it was what everyone was talking about the next day.…”

Whitney B. said “Louis Pettenelli provided a stellar trio of talented musicians for our 1920’s-themed fundraiser event. They were professional and sounded great! Would…”

Harika D. said “Completely blown away, not only by the amazing magic tricks, but by how creative, humorous, engaging, and just fun Magic Fred was for our virtual kids…”

Liz C. said “Santa Bob was amazing! Even the adults were blown away by how cool this was. And the kids can’t stop talking about seeing Santa! I cannot recommend Santa…”

Mj said “We had Munsey's Magic for our son's 6th birthday party and it was a HUGE HIT. Not only were the kids entertained- so were the adults! Would…”

Peter Kostopoulos Music offers you a unique musical entertainment experience. Either as a single performer or as a duet with a female vocalist, we play the standard…

Gina C. said “Yolanda was an amazing bartender and made all of my guests feel very comfortable. She brought a personal field to the event and it didn’t feel like the…”

Marie A. said “Mel was so fun !! Made our party a huge success ❤️”

Elanor B. said “The Brighton Jazz Trio played for a gala I organized at MIT. They were absolutely wonderful, sounded amazing, were so flexible and willing to work with…”

Susan C. said “Fred Woodard and his jazz band could not have done a better job at my recent corporate event in Boston. The stakes were very, very high for my company…”

Elevate your event with ChillyTwixt, the premier mobile bar service that brings the perfect blend of style, convenience, and exceptional cocktails to your doorstep.…

Laura G. said “I booked old Towne carolers for a cousins Christmas event which we do every year. It was simply magical! The children and adults were all mesmerized by…”

Faith M. said “We had Santa Jack come to our neighborhood party! He was amazing and the children loved him. Highly recommend!”

Elan R. said “I saw Zach perform with his trio at a salsa themed event a few months ago. It's really unbelievable his skill playing latin-styled tumbaos. He is…”

Ujjayant said “Very happy with service”

Daniel N. said “The George Farrell Group far exceeded our expectations, there were many comments from our guests as to how great George's Trio sounded and how much…”