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491 Wedding Entertainers serving Winchester, MA

Featured

Orchid Reed Band

5.0 (6)
Top Performer
7 Verified bookings

  • Somerville, MA
  • Wedding Band / Wedding Entertainment
  • 5 miles from Winchester
  • Contact for pricing

Jessica P. said “We hired Orchid Reed for our department’s lunch party and they were excellent! They were able to accommodate a last minute location change with no issues. The musicians are amazingly talented and we...”
Featured

Matt Roberts: Clean Comedy Magic

5.0 (74)
Top Performer
120 Verified bookings

  • Boston, MA
  • Magician / Wedding Entertainment
  • 8 miles from Winchester
  • Contact for pricing

Jeanette B. said “Matt did table side magic for 150+ seniors for our annual National Asisted Living Week Luncheon this past week and he was phenomenal! Very impressive, got the crowd going between dancing & dinner &...”
Featured

Rowan Gemma, Violinist and Composer

4.98 (31)
Top Performer
56 Verified bookings

  • Boston, MA
  • Violinist / Wedding Entertainment
  • 8 miles from Winchester
  • Contact for pricing

Katie C. said “Rowan was absolutely fantastic to work with from start to finish. He was incredibly accommodating and loved all of our song selections, including some of our wild ideas. And he is unbelievably...”
Featured

Chandler Boston Magician

5.0 (11)
Top Performer
15 Verified bookings

  • Boston, MA
  • Magician / Wedding Entertainment
  • 8 miles from Winchester
  • $500 – $2,000 per event

Peter C. said “Chandler's magic was amazing. He was also quite entertaining. We hired him for an annual holiday party of about 35 people. Everyone was thoroughly impressed and enthralled. He made the evening a...”
Featured

AJ Piano Works - Restaurant, Bar, & Hotel Lounge Pianist & Singer

5.0 (17)
Top Performer
24 Verified bookings

  • Boston, MA
  • Pianist / Wedding Entertainment
  • 8 miles from Winchester
  • $200 – $800 per event

Sam P. said “I would highly recommend AJ. He prepared three songs for our wedding ceremony and played prelude music while guests arrived. He was very communicative and accommodating to our requests. A fantastic...”
Featured

Dan Alan Levine Music

5.0 (6)
Top Performer
18 Verified bookings

  • Boston, MA
  • Pianist / Wedding Entertainment
  • 8 miles from Winchester
  • $325 – $2,500 per event

Patricia L. said “Delightful music for my daughter's bridal shower!”
Featured

Gillian Berkowitz

5.0 (48)
Top Performer
58 Verified bookings

  • Natick, MA
  • Pianist / Wedding Entertainment
  • 16 miles from Winchester
  • Starts at $500

Bora Y. said “Gillian was an absolute joy to have at our intimate family celebration. She has such a calm and sweet demeanor, and she approached every guest with genuine attention. She took the time to ask how...”
Featured

Great Scott Productions

4.82 (77)
Top Performer
160 Verified bookings

  • Rockland, MA
  • Magician / Wedding Entertainment
  • 25 miles from Winchester
  • Starts at $100

Berry X. said “we had a great time with The Great Scott!”
Featured

Dave Macklin Band

5.0 (25)
21 Verified bookings

  • Brighton, MA
  • Dance Band / Wedding Entertainment
  • 7 miles from Winchester
  • Contact for pricing

Maddie S. said “Loved the communication, dedication, and entertainment!”
Featured

Serenade Events

4.27 (160)
397 Verified bookings

  • Boston, MA
  • String Quartet / Wedding Entertainment
  • 8 miles from Winchester
  • $150 – $1,500 per event

Marie P. said “She did a great job”
Featured

Mega Magic- Magician Mike D'Urzo

5.0 (23)
23 Verified bookings

  • Boston, MA
  • Magician / Wedding Entertainment
  • 8 miles from Winchester
  • Contact for pricing

Kristina T. said “Mike put on an awesome show. He was punctual, prepared and very organized. He was engaging with the crowd and was just an absolute pleasure to be around. Everyone was amazed by his talent. Fun was...”
Featured

Cape Cod String Quartet

5.0 (62)
24 Verified bookings

  • Boston, MA
  • Violinist / Wedding Entertainment
  • 8 miles from Winchester
  • Contact for pricing

Kathy B. said “I reached out to Dan TWO days before our surprise wedding. Dan was incredibly responsive. My expectations weren’t very high because I booked in such a rush. Dan made our night so incredibly magical...”
Featured

Frank the Dj

5.0 (1)
4 Verified bookings

  • Boston, MA
  • Wedding DJ / Wedding Entertainment
  • 8 miles from Winchester
  • Contact for pricing

Chris P. said “DJ Frank was very professional, accommodating, and prompt! He provided entertainment and organization to a wonderful 50th wedding anniversary party in a wonderful venue! DJ Frank kept the music...”
Featured

Vibrant

4.93 (27)
19 Verified bookings

  • Boston, MA
  • Wedding Band / Wedding Entertainment
  • 8 miles from Winchester
  • Starts at $3,000

Kathryn J. said “Vibrant exceeded all expectations for our wedding. They were total pro’s and learned two new songs for us, which sounded like they had been practicing and performing for years. They were highly...”
Featured

Jason Ji Guitarist

5.0 (14)
19 Verified bookings

  • Boston, MA
  • Guitarist / Wedding Entertainment
  • 8 miles from Winchester
  • Contact for pricing

Jessica A. said “Jason was outstanding in every way. He played 3 hours supporting vocalist Connor Antico. Thank you Jason, looking forward to when you work again with Connor. Thank you.”
Featured

Angela Zorrilla Music Services

5.0 (9)
13 Verified bookings

  • Quincy, MA
  • Violinist / Wedding Entertainment
  • 15 miles from Winchester
  • Contact for pricing

Ryan D. said “Angela helped me with my surprise proposal. She was very communicative and reduced so much of my stress throughout the process. And the music was beautiful. Highly recommend. ”
Featured

The Donnino Mentalists - Beyond Imagination!

5.0 (16)
14 Verified bookings

  • Westwood, MA
  • Magician / Wedding Entertainment
  • 17 miles from Winchester
  • Starts at $400

Christine G. said “The entire Donnino family was amazingly entertaining. Their performance left our guests in awe! As a family campground, it was the perfect act to book for an evening that was appropriate for all ages....”
Featured

IT Factor Live Entertainment

4.42 (15)
10 Verified bookings

  • Weymouth, MA
  • Wedding DJ / Wedding Entertainment
  • 19 miles from Winchester
  • $400 – $2,500 per event

Sloane K. said “We had a great time with DJ Benson!! Made our day so special and fun! His son was also such a joy and had great dance moves!!!”
Featured

Munsey's Magic

5.0 (84)

  • Medford, MA
  • Magician / Wedding Entertainment
  • 3 miles from Winchester
  • Contact for pricing

L N. said “I hosted a surprise party for my friends 28th birthday. We had 16 guests. Not only did Jim carefully cooperate with me for the surprise to happen, he was an incredibly thoughtful guest! There was a...”
Featured

KTO Band

5.0 (2)

  • Boston, MA
  • Wedding Band / Wedding Entertainment
  • 8 miles from Winchester
  • Contact for pricing

Courtney H. said “We hired KTO band for our wedding two weeks ago and not only was Katie and her team wonderful to work with, the band was a huge highlight of our wedding and all of our guests made sure we knew so!...”
Featured

  • Boston, MA
  • Wedding Band / Wedding Entertainment
  • 8 miles from Winchester
  • Contact for pricing

Zach A. L. R. said “Cover story performed at our wedding this past summer, they did an excellent job, their performance was superb! They really went above and beyond to ensure the event was a success! I would highly...”
Featured

Memento

5.0 (1)
New member

  • Boston, MA
  • Photo Booths / Wedding Entertainment
  • 8 miles from Winchester
  • Contact for pricing

Marco F. said “Memento Photo Booth was absolutely incredible! From the initial communication through the end of our event, the team was professional, responsive, organized, and genuinely committed to making the...”
Featured

  • Littleton, MA
  • Magician / Wedding Entertainment
  • 20 miles from Winchester
  • Starts at $295

I use the art of magic to bring wonder, laughter, and memorable moments to audiences of all ages. From children’s birthday parties to strolling magic at...

Jack Miller Magic

5.0 (3)
Top Performer
11 Verified bookings

  • Arlington, MA
  • Magician / Wedding Entertainment
  • 3 miles from Winchester
  • Starts at $400

Srividya M. said “Jack made the event so much fun and catered to all ages it was a success!”

Mel Stiller

5.0 (8)
Top Performer
11 Verified bookings

  • Waltham, MA
  • Pianist / Wedding Entertainment
  • 7 miles from Winchester
  • Starts at $300

Pamela P. said “Mel was excellent. He came on time, played a list of requested music and the crowd really loved having a piano player at this function. I would highly recommend him.”

Dave MacDonald

4.92 (149)
Top Performer
394 Verified bookings

  • Chelmsford, MA
  • Caricaturist / Wedding Entertainment
  • 16 miles from Winchester
  • $100 – $150 per hour

Megan R. said “We had a small “corporate” event of about 60ish people. Dave banged out tons of portraits for my employees and they all loved it! 10/10 recommend Dave and will hire again when needed. Thanks Dave!”

Santiago Lopez - Professional Guitarist

5.0 (1)
1 Verified booking

  • Somerville, MA
  • Guitarist / Wedding Entertainment
  • 5 miles from Winchester
  • Contact for pricing

Guillermo V. said “Santiago was very professional and sounded great. Takes requests from the crowd and showed up on time. ”

Peter O'Malley is Magic

5.0 (4)
3 Verified bookings

  • Boston, MA
  • Magician / Wedding Entertainment
  • 8 miles from Winchester
  • Contact for pricing

Lorie K. said “Peter O'Malley is a true magician. He engages the crowd and makes it fun for all. ”

Caricatures by Josh

5.0 (9)
21 Verified bookings

  • Salem, MA
  • Caricaturist / Wedding Entertainment
  • 13 miles from Winchester
  • Starts at $100 per hour

Candice M. said “Josh was very professional, easy to work with, and created awesome caricatures of our students for our school event!”

The Magic of Joe Ferranti

5.0 (26)
Top Performer
33 Verified bookings

  • Wilmington, MA
  • Magician / Wedding Entertainment
  • 7 miles from Winchester
  • Starts at $300

Ester D. said “Really good! Everybody enjoyed the card tricks”

Cam Olver

5.0 (6)
Top Performer
9 Verified bookings

  • Brighton, MA
  • Guitarist / Wedding Entertainment
  • 7 miles from Winchester
  • $200 – $600 per event

Taylor B. said “I asked for a last minute, kind of broad request for a retail store event and Cam responded quickly with examples of what songs he would play, really showing that he knew our brand and what vibes we...”

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About booking Wedding Entertainment in Winchester, MA

Wedding entertainment brings your celebration to life, creating unforgettable moments on your big day. From talented harpists to interactive fire performers to a talented wedding DJ, the right entertainment sets the tone and keeps the energy flowing. The perfect wedding entertainers also add a personal touch, making your wedding day feel unique and tailored to your preferences and vision.

The cost of hiring unique wedding entertainment in Winchester, Massachusetts will vary depending on the types of performers you want to hire and how long you want them to entertain. Wedding performers require varying spaces to perform, so consider your venue when reviewing wedding entertainment ideas. Contact the wedding entertainers above to discuss your special day and receive a customized quote.

While exploring Winchester wedding entertainment companies, thoroughly review profile information, look at photos, and watch videos to understand the type of performance or service they offer. Read reviews from past clients to gain valuable insight into their experience level and ability to meet your expectations. Remember to include important details like venue information, wedding themes, and preferences to receive the most accurate quote.

Once you find the entertainer you want to hire, finalize the booking on GigSalad. Our full-service platform makes it easy to book wedding entertainment. 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 enjoy your wedding day!

Wedding Entertainment serving the Winchester, MA area

These Wedding Entertainment serve the wider Winchester and Middlesex county area and travel to West Medford, Woburn, Stoneham, Arlington, Medford, Arlington Heights, Melrose, Malden, Belmont, Lexington, Burlington, Wakefield, Somerville, Waverley, Everett, Reading, North Waltham, Cambridge, Watertown, New Town, Charlestown, Saugus, Chelsea, Allston, Wilmington, Pinehurst, Revere, Hanscom Afb, Nonantum, and Waltham.

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