The 237 Best Holiday Party Entertainers for Hire in Winchester, MA

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

Sheilah B. said “We had Matt for entertainment at our wedding this past weekend. He was absolutely fantastic! We had 7 of our grandchildren there and he involved the older…”

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…”

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…”

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

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…”

Jennifer H. said “Santa and Mrs. Clause were amazing!!! The kids were over the moon, it will truly be a childhood memory they can remember. I could not have asked for a…”

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…”

Martin K. said “Santa Scott did a great job. He arrived on time, made a great entrance to the venue. He spent some time withe the kids and adults. We sang songs, he told…”

Alexandra T. said “We hired Joe to do some strolling magic at our company holiday party. Everyone absolutely loved him and his magic tricks left us all in shock!!! Very…”

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.…”

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

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…”

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 :)”

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…”

Happy Jazz provides the perfect background jazz music for your event. Weddings, Cocktail Hours, Corporate Events, Birthday Parties and more!

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…

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

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…”

Kimberley H. said “We hosted Mrs. Claus at a private event room in a hotel for our 8 grandkids while we attended a wedding. She was very engaged and the kids were very happy…”

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…”

Brad H. said “Santa jack was amazing with the kinda and all around a great guy. Highly recommend him”

Ujjayant said “Very happy with service”

Melissa M. said “They were fantastic, on time and a huge crowd pleaser.”