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446 Holiday Party Entertainers serving Milford, MA

Featured

Santa MetroWest

5.0 (43)
Top Performer
97 Verified bookings

  • Framingham, MA
  • Santa Claus / Holiday Party Entertainment
  • 11 miles from Milford
  • $225 – $250 per event

Carol D. said “Little ones and even the adults enjoyed Santa. Santa was very interactive with the kids and he gave out gifts to both kids and adults. We sang "Rudolph the Red Nosed Reindeer" with Santa. ...”
Featured

Gillian Berkowitz

5.0 (48)
Top Performer
58 Verified bookings

  • Natick, MA
  • Pianist / Holiday Party Entertainment
  • 13 miles from Milford
  • Starts at $500

Christopher V. said “Worked with Gillian for a private reception for approximately 60 guests. From the start, she was responsive, professional, and upbeat in communication. She arrived early on the day of the event and...”
Featured

D'Amico Entertaintainment

5.0 (88)
Top Performer
45 Verified bookings

  • Providence, RI
  • Jazz Band / Holiday Party Entertainment
  • 22 miles from Milford
  • Contact for pricing

Gary D. said “Music was great, consistent, and professionally executed. ”
Featured

Santa Phil, Mrs Claus and their Magic Tesla

4.94 (19)
Top Performer
52 Verified bookings

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

Katie C. said “Loved how they sung songs with instruments, read a story, engaged the kids, and of course the Tesla show.”
Featured

Santa Jolly Pauly

5.0 (7)
Top Performer
3 Verified bookings

  • Seekonk, MA
  • Santa Claus / Holiday Party Entertainment
  • 25 miles from Milford
  • Contact for pricing

Kristin F. said “Santa Jolly Pauly was a hit. The children (& adults) at our family Christmas party loved him. Him and Mrs. Claus also joined. They were interactive with the children and ensured we were able to...”
Featured

Bruce Kalver - Magician

5.0 (4)
Top Performer
7 Verified bookings

  • Cranston, RI
  • Magician / Holiday Party Entertainment
  • 25 miles from Milford
  • Starts at $300

Mary R. said “We hired Bruce super last minute for our friend’s bachelorette party in Newport, Rhode Island, and he was AMAZING! He showed up right on time, ready to go, and was so friendly and easygoing with our...”
Featured

Santa Dan

4.99 (104)
Top Performer
268 Verified bookings

  • Taunton, MA
  • Santa Claus / Holiday Party Entertainment
  • 27 miles from Milford
  • $175 – $1,000 per event

Monica C. said “This was our 3rd year having Santa Dan visit our home in Christmas Eve. He is always jolly, on time and the children love him. ”
Featured

Chandler Boston Magician

5.0 (11)
Top Performer
15 Verified bookings

  • Boston, MA
  • Magician / Holiday Party Entertainment
  • 28 miles from Milford
  • $500 – $2,000 per event

Brendan R. said “Hey was incredible and the talk of the party. I had folks as old as 75 and as young as 6 at the party and all were amazed. Seamlessly blended into the party and was just a joy to have. Couldn't...”
Featured

The Creswell Club

5.0 (32)
Top Performer
43 Verified bookings

  • Boston, MA
  • Jazz Band / Holiday Party Entertainment
  • 28 miles from Milford
  • Starts at $1,200 per hour

Matthew C. said “Controlled the atmosphere set the mardi gras vibe”
Featured

Jazz Breeze

5.0 (29)
Top Performer
47 Verified bookings

  • Boston, MA
  • Jazz Band / Holiday Party Entertainment
  • 28 miles from Milford
  • Contact for pricing

Austin S. said “Jazz Breeze was such a pleasure to work with when planning for our wedding welcome dinner event. Marlene's communication was super efficient and informative. She checked in on me, but did not pressure...”
Featured

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

5.0 (17)
Top Performer
24 Verified bookings

  • Boston, MA
  • Pianist / Holiday Party Entertainment
  • 28 miles from Milford
  • $200 – $800 per event

Christopher E. said “It was a distinct pleasure to have the opportunity to work with AJ for my engagement party. AJ was generous with his time, meeting with me the night before to go through logistics, and to do a...”
Featured

Gerry Beaudoin Trio

4.97 (40)
Top Performer
59 Verified bookings

  • Boston, MA
  • Jazz Band / Holiday Party Entertainment
  • 28 miles from Milford
  • $250 – $5,000 per event

Mike P. said “For an event at the Bostonia public, this was perfect ambiance for our business cocktail event. I received so many compliments about the music and actually struck up a conversation about jazz with a...”
Featured

Dan Alan Levine Music

5.0 (6)
Top Performer
18 Verified bookings

  • Boston, MA
  • Pianist / Holiday Party Entertainment
  • 28 miles from Milford
  • $325 – $2,500 per event

Edgar K. said “Dan met our expectations to provide the musical entertainment for my 80th birthday celebration. For any suitable future occasion, I would like to engage him again.”
Featured

NewBartenders

5.0 (2)
Top Performer
3 Verified bookings

  • Boston, MA
  • Bartender / Holiday Party Entertainment
  • 28 miles from Milford
  • Starts at $500

Denise B. said “We hired him for my mom’s 70th birthday and he absolutely made the night. The cocktails were fantastic, he kept the energy up all evening with fun drink tricks, and he even made Shirley Temples for...”
Featured

Matt Roberts: Clean Comedy Magic

5.0 (74)
Top Performer
120 Verified bookings

  • Boston, MA
  • Magician / Holiday Party Entertainment
  • 28 miles from Milford
  • Contact for pricing

Devon H. said “My friends and family are still talking about how awesome Matt's performance was at our Halloween party! The party was for young children and their parents, and I hired Matt to perform walk-around...”
Featured

Shadowbreeze

5.0 (2)
Top Performer
3 Verified bookings

  • Boston, MA
  • Jazz Band / Holiday Party Entertainment
  • 28 miles from Milford
  • Contact for pricing

Suzanne T. said “We were fortunate enough to have Shadowbreeze play our latest event at Wickford Yacht Club. They were fantastic, had a large repertoire of songs, and played and sang beautifully. Additionally they...”
Featured

Great Scott Productions

4.82 (77)
Top Performer
160 Verified bookings

  • Rockland, MA
  • Magician / Holiday Party Entertainment
  • 31 miles from Milford
  • Starts at $100

Renee L. said “Scott came dressed with a Harry Potter costume which the kids loved because that was the theme of the party. His tricks were funny and very clever. He had everyone at the edge of their seats for every...”
Featured

Santa Bubba

5.0 (25)
Top Performer
40 Verified bookings

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

Tracy M. said “From the first contact to the final goodbye, Santa Bubba was incredibly kind and easy to work with. The kiddos were enraptured as he read a book, dispelled doubts with evidence of the universal...”
Featured

GL3 Magic

5.0 (1)
1 Verified booking

  • Shrewsbury, MA
  • Magician / Holiday Party Entertainment
  • 15 miles from Milford
  • 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

The Donnino Mentalists - Beyond Imagination!

5.0 (16)
14 Verified bookings

  • Westwood, MA
  • Magician / Holiday Party Entertainment
  • 16 miles from Milford
  • Starts at $400

Jonathan G. said “The Donnino Mentalists put on a great show for us at our summer program. All of our students were excited and clamoring to get up on stage. They left me speechless at the end and I would be glad to...”
Featured

Jolly Santa JD

5.0 (2)
2 Verified bookings

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

Bob S. said “We had a big TOYS FOR TOTS event and Santa arrived with a sack full of new toys to add to the donations. After the grand entrance he went to the back of the room where there was a small contingent...”
Featured

Todd Brunel Musical Groups

5.0 (4)
6 Verified bookings

  • Arlington, MA
  • Jazz Band / Holiday Party Entertainment
  • 26 miles from Milford
  • Starts at $200

Gina B. said “I can't praise them enough! Great music! Not only were they so talented they helped when our party got thrown off schedule and we needed the music to play longer! So grateful for them!! Would...”
Featured

Exquisite Event Services

4.76 (78)
144 Verified bookings

  • Arlington, MA
  • Bartender / Holiday Party Entertainment
  • 26 miles from Milford
  • Contact for pricing

Rachael B. said “David + Team help out with a large graduation party. David provided two helpers for the event who were EXCELLENT, highly trained, extremely courteous, smart, and professionally dressed. I walked...”
Featured

Morgan Treni & The Golden Estate House Band

5.0 (17)
1 Verified booking

  • Boston, MA
  • Jazz Band / Holiday Party Entertainment
  • 28 miles from Milford
  • Starts at $2,500

Geniece M. said “I can’t tell you enough how wonderful Morgan and her band is. We had them perform at our company event that included a five course dinner and wine pairing in a very intimate environment and they...”
Featured

SpeechLess

4.98 (21)
2 Verified bookings

  • Boston, MA
  • Jazz Band / Holiday Party Entertainment
  • 28 miles from Milford
  • $3,500 – $25,000 per event

Kelly M. said “My entire family was absolutely blown away! During the ceremony, my sister—the maid of honor—could barely finish her reading because Speechless Strings played such a breathtaking remembrance piece for...”
Featured

Louis Pettinelli Entertainment

4.92 (70)
249 Verified bookings

  • Boston, MA
  • Jazz Band / Holiday Party Entertainment
  • 28 miles from Milford
  • Starts at $300

Hannah M. said “Louis Pettinelli Entertainment were outstanding for our wedding reception dinner. They were so professional to work with during the contract phase and understanding what we wanted. We had a Trio...”
Featured

The Christmas Carolers, LLC

4.78 (14)
61 Verified bookings

  • Boston, MA
  • Christmas Carolers / Holiday Party Entertainment
  • 28 miles from Milford
  • Contact for pricing

Stan K. said “Such a professional group. Great communication. They made the start of our party very festive. They got great crowd interaction and were a great addition to our festivities. No hesitation to hire them...”
Featured

Holiday Victorian Carolers

4.91 (34)
65 Verified bookings

  • Boston, MA
  • Christmas Carolers / Holiday Party Entertainment
  • 28 miles from Milford
  • Contact for pricing

Melissa M. said “The group arrived promptly, and were dressed in wonderful Victorian clothing. They provided an array of songs, some religious and some just fun. They took requests, and engaged with guests. Everyone...”
Featured

Mega Magic- Magician Mike D'Urzo

5.0 (23)
23 Verified bookings

  • Boston, MA
  • Magician / Holiday Party Entertainment
  • 28 miles from Milford
  • Contact for pricing

Ashley R. said “Mike’s performance at my Birthday Party at Casa Loma , Toronto on Oct 6, 2025 left our 60 guests in awe and puzzling as to how he was able to execute what appeared to be impossible tricks, some of...”
Featured

Santa Gary

5.0 (5)
7 Verified bookings

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

Konstantinos P. said “Santa Gary brought his Christmas spirit to the 200+ kids and families at Goodwill's Annual Youth Holiday Celebration this year. He was an absolute joy with the children and families. 10/10”
Featured

Andrew Kaplan

4.87 (25)
47 Verified bookings

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

James E. said “Andy was great! He arrived early, confirmed what he was wearing was appropriate, gave us couple of play lists, then "tested" the piano so he could get accustomed to it prior to the guests...”
Featured

The "D" TRAIN

5.0 (1)
1 Verified booking

  • Warwick, RI
  • Jazz Band / Holiday Party Entertainment
  • 31 miles from Milford
  • $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...”

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About booking Holiday Party Entertainment in Milford, 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 Milford, 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 Milford 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 Milford, MA area

These Holiday Party Entertainment serve the wider Milford and Worcester county area and travel to Hopedale, Mendon, Bellingham, Upton, Medway, Hopkinton, Holliston, Blackstone, Northbridge, Woodville, Linwood, Franklin, Uxbridge, North Uxbridge, Whitinsville, Millville, Millis, Ashland, Woonsocket, Sheldonville, Grafton, South Grafton, Norfolk, Forestdale, Sherborn, Slatersville, Westborough, Fayville, Wrentham, and Framingham.

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