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439 Holiday Party Entertainers serving Watertown, MA

Featured

Shadowbreeze

5.0 (2)
Top Performer
3 Verified bookings

  • Boston, MA
  • Jazz Band / Holiday Party Entertainment
  • 6 miles from Watertown
  • 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

Chandler Boston Magician

5.0 (11)
Top Performer
15 Verified bookings

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

Michael M. said “Chandler stealthily swooped into my birthday and kept the guests raptured throughout his time. A nice guy and a vlsss act’”
Featured

D'Amico Entertaintainment

5.0 (88)
Top Performer
45 Verified bookings

  • Boston, MA
  • Jazz Band / Holiday Party Entertainment
  • 6 miles from Watertown
  • Contact for pricing

Haley C. said “John was excellent! Perfect accompaniment to our night of history at a former jazz club/ new development project.”
Featured

The Creswell Club

5.0 (32)
Top Performer
43 Verified bookings

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

Tiffany R. said “Dan and his band helped make our amazing day even more special. They were on time, polite, quick to setup, and were flexible in terms of our special request: we had asked Dan himself to announce the...”
Featured

Matt Roberts: Clean Comedy Magic

5.0 (74)
Top Performer
120 Verified bookings

  • Boston, MA
  • Magician / Holiday Party Entertainment
  • 6 miles from Watertown
  • Contact for pricing

Elizabeth R. said “Matt did a great job keeping the attention of my daughter and her friends for her 16th birthday party. The girls had a great time watching the magic!”
Featured

Dan Alan Levine Music

5.0 (6)
Top Performer
18 Verified bookings

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

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 music. Perfect. I would highly recommend...”
Featured

NewBartenders

5.0 (2)
Top Performer
3 Verified bookings

  • Boston, MA
  • Bartender / Holiday Party Entertainment
  • 6 miles from Watertown
  • 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

Gerry Beaudoin Trio

4.97 (40)
Top Performer
59 Verified bookings

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

Graham B. said “Gerry and his guys were easy to work and very professional both leading up to and at the event. They were the perfect backdrop to our guest arriving and cocktail hour! I couldn’t recommend them...”
Featured

Jazz Breeze

5.0 (29)
Top Performer
47 Verified bookings

  • Boston, MA
  • Jazz Band / Holiday Party Entertainment
  • 6 miles from Watertown
  • Contact for pricing

Kelsey R. said “Marlene and Jazz Breeze did an absolutely amazing job playing our wedding. We booked a quartet (piano, bass, drums, sax). They had tremendous energy in the music they played and they accommodated...”
Featured

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

5.0 (17)
Top Performer
24 Verified bookings

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

Alena C. said “Our wedding was this past weekend and AJ’s presence during our cocktail hour added so much class and elegance to the event. He played beautifully and our guests could not stop talking about him! So...”
Featured

Santa Bob

5.0 (11)
Top Performer
14 Verified bookings

  • Mattapan, MA
  • Santa Claus / Holiday Party Entertainment
  • 8 miles from Watertown
  • Starts at $200

Jen H. said “Santa Bob did a great job at our event - had a great experience!”
Featured

Gillian Berkowitz

5.0 (48)
Top Performer
58 Verified bookings

  • Natick, MA
  • Pianist / Holiday Party Entertainment
  • 11 miles from Watertown
  • Starts at $500

Ed H. said “Gillian, it was truly a pleasure having you perform at my mom’s 80th birthday party! You are as nice as you are talented. Thank you!”
Featured

Santa MetroWest

5.0 (43)
Top Performer
97 Verified bookings

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

Samantha M. said “We had the absolute pleasure of have Santa Metrowest come to our home for our family Christmas party. He has to be the most authentic Santa we have seen! The children loved him and enjoyed his...”
Featured

Great Scott Productions

4.82 (77)
Top Performer
160 Verified bookings

  • Rockland, MA
  • Magician / Holiday Party Entertainment
  • 21 miles from Watertown
  • Starts at $100

Priyanka R. C. said “I booked Scott for my 5-year old Birthday Party, and he did Magic with characters. It was extremely entertaining and he was able to keep a mixed crowd of under 10 year old completely hooked for over...”
Featured

Todd Brunel Musical Groups

5.0 (4)
6 Verified bookings

  • Arlington, MA
  • Jazz Band / Holiday Party Entertainment
  • 3 miles from Watertown
  • 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
  • 3 miles from Watertown
  • Contact for pricing

Shanna S. said “I booked waitstaff about a week ahead for Memorial Day Weekend graduation party. Communication was prompt and pricing better than others. Staff arrived early and ready to do anything we needed. Made...”
Featured

Holiday Victorian Carolers

4.91 (34)
65 Verified bookings

  • Boston, MA
  • Christmas Carolers / Holiday Party Entertainment
  • 6 miles from Watertown
  • Contact for pricing

Kaleigh S. said “Our residents and their families loved them!”
Featured

Morgan Treni & The Golden Estate House Band

5.0 (17)
1 Verified booking

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

Giuliana B. said “The Golden Estate Band performed at my sister’s wedding. Morgan was a dream to work with through the whole planning process. The band was amazing and our guests danced the night away. Everyone still...”
Featured

SpeechLess

4.98 (21)
2 Verified bookings

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

Jennifer S. said “My husband and I spent a lot of time researching music for our wedding because it was one of the most important elements of our day. I had always dreamed of walking down the aisle to violin,...”
Featured

Mega Magic- Magician Mike D'Urzo

5.0 (23)
23 Verified bookings

  • Boston, MA
  • Magician / Holiday Party Entertainment
  • 6 miles from Watertown
  • Contact for pricing

Leann L. said “The team had a GREAT time! They loved you and the event. They were so excited and speechless after we hung up with you. They’re still trying to figure out how you pulled off what you did! We all...”
Featured

The Christmas Carolers, LLC

4.78 (14)
61 Verified bookings

  • Boston, MA
  • Christmas Carolers / Holiday Party Entertainment
  • 6 miles from Watertown
  • Contact for pricing

Roberta N. said “The group was excellent. My only regret was that the party was so noisy it was hard to hear them. I was very pleased with their performance.”
Featured

Louis Pettinelli Entertainment

4.92 (70)
249 Verified bookings

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

Nadia H. said “The Jazz Duo was amazing, our guests loved the entertainment. They were a classy addition to our event”
Featured

Marvelous Santas

4.99 (57)
102 Verified bookings

  • Saugus, MA
  • Santa Claus / Holiday Party Entertainment
  • 11 miles from Watertown
  • $50 – $400 per event

Veronica Z. said “Hired he and his wife to be a European king and queen in appropriate costumes they were Outstanding at my garden party...greeting guests, etc. Such a pleasure to deal with!!!”
Featured

The Donnino Mentalists - Beyond Imagination!

5.0 (16)
14 Verified bookings

  • Westwood, MA
  • Magician / Holiday Party Entertainment
  • 11 miles from Watertown
  • Starts at $400

Kristin M. said “The Donnino Mentalists were the "entertainment" for our end-of-year holiday gathering for our team at work. Everyone loved the show! People were involved but didn't feel put on the spot. Our team...”
Featured

Munsey's Magic

5.0 (84)

  • Medford, MA
  • Magician / Holiday Party Entertainment
  • 5 miles from Watertown
  • Contact for pricing

Ailce L. said “Jim is an amazing magician and just a fantastic human being in general. His tricks left us in awe (and smiles) and we cannot recommend him highly enough. We were thoroughly entertained and also just...”
Featured

  • Boston, MA
  • Bartender / Holiday Party Entertainment
  • 6 miles from Watertown
  • Starts at $450

Copa Mobile Bar delivers a fully customizable bar experience to events across New England. From elegant weddings to lively corporate parties and intimate...
Featured

  • Littleton, MA
  • Magician / Holiday Party Entertainment
  • 20 miles from Watertown
  • Contact for pricing

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...

Mel Stiller

5.0 (8)
Top Performer
11 Verified bookings

  • Waltham, MA
  • Pianist / Holiday Party Entertainment
  • 3 miles from Watertown
  • Starts at $300

Dianna said “Mel was amazing!! A great pianist and perfect entertainer for sing along .. all our guests had a fabulous night!!! Definitely choose him again!! Thank you !!”

Jack Miller Magic

5.0 (2)
Top Performer
11 Verified bookings

  • Arlington, MA
  • Magician / Holiday Party Entertainment
  • 3 miles from Watertown
  • Starts at $400

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

North Pole Santa John

4.84 (24)
Top Performer
52 Verified bookings

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

Aileen S. said “Santa John showed up on time and surprised us with Mrs. Claus. They were both wonderful with our children and family. Thank you so much for keeping the magic in Christmas. ”

On the Rocks and Road

5.0 (2)
Top Performer
2 Verified bookings

  • Andover, MA
  • Bartender / Holiday Party Entertainment
  • 20 miles from Watertown
  • $750 – $3,500 per event

Alex F. said “We hired On the Rocks and Road for our wedding and they were fantastic. Jackie and Cindy were incredibly helpful from the very start. They helped us figure out our menu, designed excellent cocktails...”

Santa Paul

5.0 (8)
Top Performer
21 Verified bookings

  • Dracut, MA
  • Santa Claus / Holiday Party Entertainment
  • 22 miles from Watertown
  • Starts at $200

Elizabeth L. said “I wish Christmas came more than once a year so we could have Santa Paul visit us again. He was so wonderful and I hope we can use him again next year!”

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

These Holiday Party Entertainment serve the wider Watertown and Middlesex county area and travel to Waverley, Nonantum, Newton Corner, Belmont, Brighton, Newtonville, West Newton, Chestnut Hill, Newton, Waltham, New Town, Allston, North Waltham, Newton Center, Arlington, Arlington Heights, Auburndale, Cambridge, Newton Highlands, Waban, Brookline, Brookline Village, Somerville, West Medford, Newton Upper Falls, Newton Lower Falls, Medford, Roxbury Crossing, Jamaica Plain, and Lexington.

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