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410 Holiday Party Entertainers serving Webster, MA

Featured

Santa Bubba

5.0 (25)
Top Performer
40 Verified bookings

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

Bridget said “Santa Bubba was a great addition to our family brunch! He had a nice list, a bell, pictures of the reindeer and even called his elves from the North Pole! He was so nice to the kids (and adults...”
Featured

Santa Phil, Mrs Claus and their Magic Tesla

4.94 (19)
Top Performer
52 Verified bookings

  • Providence, RI
  • Santa Claus / Holiday Party Entertainment
  • 29 miles from Webster
  • $200 – $500 per event

Dana M. said “Mr. & Mrs., Claus were a big hit at our recent children's Christmas Party. It was nice that they took some time at the end of the gift giving to sit and talk with all of the children gathered...”
Featured

D'Amico Entertaintainment

5.0 (88)
Top Performer
45 Verified bookings

  • Providence, RI
  • Jazz Band / Holiday Party Entertainment
  • 29 miles from Webster
  • Contact for pricing

John B. said “Excellent communication throughout the process. Violinist was excellent and performed all the requested songs perfectly. This was absolutely worth every penny.”
Featured

Bruce Kalver - Magician

5.0 (4)
Top Performer
7 Verified bookings

  • Cranston, RI
  • Magician / Holiday Party Entertainment
  • 29 miles from Webster
  • Starts at $300

Evan W. said “Bruce is a legend in the industry and 100% worth inviting to your next event. Was very funny and his 60 years of experience shined through - still have no idea how his hands were able to move so fast....”
Featured

Gillian Berkowitz

5.0 (48)
Top Performer
58 Verified bookings

  • Natick, MA
  • Pianist / Holiday Party Entertainment
  • 32 miles from Webster
  • Starts at $500

Amy S. said “Gillian was so wonderful! Her playing was delightful and warm and set the perfect tone for our intimate holiday party. Would highly recommend!”
Featured

Gabriel Landstedt, Pianist

5.0 (3)
Top Performer
4 Verified bookings

  • Norwich, CT
  • Pianist / Holiday Party Entertainment
  • 38 miles from Webster
  • Contact for pricing

Diane N. said “We had the pleasure of having Gabriel, a classical pianist to perform during our celebration of life event. He was an absolute pleasure & exceeded all our expectations. He was warm, professional &...”
Featured

GL3 Magic

5.0 (1)
1 Verified booking

  • Shrewsbury, MA
  • Magician / Holiday Party Entertainment
  • 19 miles from Webster
  • Contact for pricing

Alyssa M. said “Isaac was great for our annual Halloween Party! His communication, timeliness and willingness to be flexible are to be commended. We had mainly teenagers and parents, and he truly astounded all with...”
Featured

Jolly Santa JD

5.0 (2)
2 Verified bookings

  • North Scituate, RI
  • Santa Claus / Holiday Party Entertainment
  • 21 miles from Webster
  • Starts at $250

Joe K. said “Santa JD was beyond fantastic at our holiday party we held. He looked the part for sure and the way he interacted with the children was beyond my expectations. The children had a great experience...”
Featured

Andrew Kaplan

4.87 (25)
47 Verified bookings

  • West Warwick, RI
  • Pianist / Holiday Party Entertainment
  • 30 miles from Webster
  • Starts at $125

Rebecca L. said “Andrew played at my company's holiday party. It was excellent and everyone enjoyed it. He communicated well and responded quickly to messages.”
Featured

Santa Gary

5.0 (5)
7 Verified bookings

  • Leominster, MA
  • Santa Claus / Holiday Party Entertainment
  • 33 miles from Webster
  • Starts at $150 per hour

Joy R. said “We had a party of about 40 people at our house. A mix of adults, teenagers and little ones. Santa was very responsive and great at figuring out what we needed for our event. He looks very professional...”
Featured

The "D" TRAIN

5.0 (1)
1 Verified booking

  • Warwick, RI
  • Jazz Band / Holiday Party Entertainment
  • 34 miles from Webster
  • $300 – $4,000 per event

Triah said “Brian and his crew are amazing. Very professional, very punctual and catered to our needs. They are great musicians who brought a certain flair to the event to make it unique. I would work with...”
Featured

  • Cumberland, RI
  • Santa Claus / Holiday Party Entertainment
  • 25 miles from Webster
  • $100 – $150 per hour

Tia C. said “From the moment Soul Santa Solomon stepped into the room, everything shifted. His presence is vibrant, warm, and absolutely electric. He doesn’t just play the role of Santa—he embodies the spirit of...”
Featured

  • Hope, RI
  • Horse Drawn Carriage / Holiday Party Entertainment
  • 28 miles from Webster
  • Contact for pricing

New England Carriage Company provides professional, compassionate horse-drawn services throughout RI, MA, CT, NH, VT, and parts of ME. We specialize in...
Featured

  • Cranston, RI
  • Bartender / Holiday Party Entertainment
  • 29 miles from Webster
  • Contact for pricing

Daniel D. said “I recently attended a craft cocktail workshop hosted by Say Yes to the Cocktail, and I must say it exceeded my expectations. The knowledgeable instructors provided a hands-on experience, teaching...”

Santa Dan & Mrs. Claus

5.0 (9)
Top Performer
12 Verified bookings

  • Webster, MA
  • Santa Claus / Holiday Party Entertainment
  • Contact for pricing

Jessica P. said “We had an amazing experience with Santa Dan! He was able to ensure that we kept the magic of Christmas alive for our little ones at a family Christmas party. He was great with the kids and we can’t...”

Rich Kringle

5.0 (21)
Top Performer
57 Verified bookings

  • Worcester, MA
  • Santa Claus / Holiday Party Entertainment
  • 15 miles from Webster
  • $225 per hour

Kristen S. said “Rich Kringle was the best Santa we could have hoped for to visit our preschool. The kids absolutely loved him. He was very soft spoken, and gave each child individualized attention as he asked them...”

North Pole Santa John

4.84 (24)
Top Performer
52 Verified bookings

  • Framingham, MA
  • Santa Claus / Holiday Party Entertainment
  • 29 miles from Webster
  • $175 – $250 per hour

Sarah K. said “Santa John was amazing! He was super friendly and made the kids feel right at home. The kids loved seeing Santa and everyone was so excited to get their presents. It was a fun, festive and memorable...”

Mel Stiller

5.0 (8)
Top Performer
11 Verified bookings

  • Waltham, MA
  • Pianist / Holiday Party Entertainment
  • 40 miles from Webster
  • Starts at $300

Chris C. said “Well done, Mel! The crowd had a great time singing along with the easy playing style of Mr. Stiller. Thanks again!”

Medway Santa Claus

4.96 (25)
61 Verified bookings

  • Medway, MA
  • Santa Claus / Holiday Party Entertainment
  • 26 miles from Webster
  • Contact for pricing

Carole C. said “Medway Santa was awesome! The kids and adults had so much fun! He provided a special memory! ”

The Laurel Tree

4.99 (23)
27 Verified bookings

  • Cranston, RI
  • Waitstaff / Holiday Party Entertainment
  • 29 miles from Webster
  • Contact for pricing

Michael D. said “You girls were great. Very professional, curtious and well organized. I felt like I was in good hands and could relax with you handling things.”

Santa New England Bob

4 Verified bookings

  • Cranston, RI
  • Santa Claus / Holiday Party Entertainment
  • 29 miles from Webster
  • $75 – $500 per event

Santa New England Christmas party’s or anytime winter spring summer or fall Xmas eve book now goes fast my beard is the real deal No fake beard here ...

Santa John J

New member

  • Northborough, MA
  • Santa Claus / Holiday Party Entertainment
  • 22 miles from Webster
  • Contact for pricing

Since 1995, I have had the extraordinary privilege of portraying Santa Claus. For me, being Santa has never been simply about putting on a costume and saying,...

The Crafted Pour Bartending

5.0 (1)
New member

  • Framingham, MA
  • Bartender / Holiday Party Entertainment
  • 29 miles from Webster
  • Contact for pricing

Jay C. said “Great service and very easy to work with. Jason was awesome suggesting everything we needed and making sure the party went off without a hitch. I highly recommend. ”

  • East Greenwich, RI
  • Pianist / Holiday Party Entertainment
  • 34 miles from Webster
  • Starts at $250

Services Offered: Vocal Soloist (English, Italian, Latin) Pianist (or mobile keyboard) Organist Vocal & Piano/Organ Duet Music Coordinator (Form a small vocal...

Party Easers

5.0 (14)

  • Cranston, RI
  • Waitstaff / Holiday Party Entertainment
  • 29 miles from Webster
  • Contact for pricing

Jen N. said “Wow, such a fantastic service! Not only did Nancy and her team take care of setting up, serving and clearing everything, they also took care of prepping the appetizers, passing hors d'oeuvres and...”

Roberto the Magician

4.88 (78)
Top Performer
111 Verified bookings

  • Worcester, MA
  • Magician / Holiday Party Entertainment
  • 15 miles from Webster
  • Contact for pricing

Samir P. said “We really enjoyed working with Roberto. He had great communication, flexibility, and he was really easy to work with. The kids and adults alike enjoyed his performance and he played to the crowd...”

Dennis The Magician

5.0 (29)
Top Performer
50 Verified bookings

  • Millville, MA
  • Magician / Holiday Party Entertainment
  • 15 miles from Webster
  • $125 – $250 per event

Kim S. said “Kept the kids engaged. The live bunny at the end was super cute! The kids loved it!”

Pepere Santa

5.0 (3)
Top Performer
8 Verified bookings

  • Woonsocket, RI
  • Santa Claus / Holiday Party Entertainment
  • 19 miles from Webster
  • Contact for pricing

Karissa M. said “We had such a great experience with Santa!! Such a fun day for all the children involved. Santa really customized our experience and gave each child their own spotlight! ”

Santa Ray

4.97 (32)
Top Performer
70 Verified bookings

  • Monson, MA
  • Santa Claus / Holiday Party Entertainment
  • 23 miles from Webster
  • Starts at $100

Kerri G. said “Did a great job with the kids ”

Santa Steve

5.0 (1)
Top Performer
7 Verified bookings

  • Pawtucket, RI
  • Santa Claus / Holiday Party Entertainment
  • 28 miles from Webster
  • Contact for pricing

Julie B. said “Santa Steve arrived on time & did a great job entertaining and taking pictures with our customers who attended our Christmas party. 10/10 would recommend! He even brought a bag of toys for the...”

Koncocted By Kelseigh Lee

5.0 (7)
Top Performer
1 Verified booking

  • Providence, RI
  • Bartender / Holiday Party Entertainment
  • 29 miles from Webster
  • Starts at $250

Marianna P. said “Kelseigh was incredible! She has helped us with our office Halloween event. Highly recommend ! We will definitely be working together again the the future. She was extremely organized, on time, drinks...”

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About booking Holiday Party Entertainment in Webster, MA

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 Webster, Massachusetts 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 Webster 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 Webster, MA area

These Holiday Party Entertainment serve the wider Webster and Worcester county area and travel to Dudley, Fabyan, Quinebaug, Grosvenor Dale, North Grosvenordale, Thompson, Oxford, East Woodstock, North Oxford, Douglas, Manchaug, Charlton, Southbridge, Woodstock, Charlton City, South Woodstock, Sutton, West Millbury, Charlton Depot, Putnam, Auburn, Rochdale, Sturbridge, Pascoag, Pomfret, Millbury, Burrillville, Whitinsville, Ballouville, and Harrisville.