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432 Holiday Party Entertainers serving Fairfield, CT

Featured

Santa Rich

4.91 (13)
Top Performer
33 Verified bookings

  • Milford, CT
  • Santa Claus / Holiday Party Entertainment
  • 12 miles from Fairfield
  • Starts at $150 per hour

Michael T. said “Santa Rich is an incredible Santa. He is a great communicator for business. He brings smiles and sentimental moment(s) to all that encounter him. At our Christmas in July event he even gave away Santa...”
Featured

Margi & the Dapper Dots

5.0 (6)
Top Performer
5 Verified bookings

  • Stamford, CT
  • Jazz Band / Holiday Party Entertainment
  • 16 miles from Fairfield
  • Contact for pricing

Phil B. said “Margi and her team were great for our vintage early 1900s event. The attendees loved all the music both vocals and Instruments. Margi was easy to work with and happy to accommodate the set to fit...”
Featured

Santa Mark CT

5.0 (5)
Top Performer
9 Verified bookings

  • Woodbridge, CT
  • Santa Claus / Holiday Party Entertainment
  • 20 miles from Fairfield
  • $175 – $400 per hour

Tamara M. said “Santa Mark was the PERFECT addition to our holiday party. He brought true Christmas Magic. I wasn’t sure how the staff would react to Santa (all adults) but the moment he walked in (he was the...”
Featured

Sassi Party Performers and Sassi Entertainment Unlimited

5.0 (25)
Top Performer
77 Verified bookings

  • Smithtown, NY
  • Santa Claus / Holiday Party Entertainment
  • 20 miles from Fairfield
  • Starts at $400

Erin W. said “Santa (aka Santa Buddha) and Mrs. Claus were absolutely wonderful at our brunch. They took time to visit every table, connect with each child, and made sure everyone had a chance for photos. The...”
Featured

Piano By Mike

5.0 (13)
31 Verified bookings

  • Fairfield, CT
  • Pianist / Holiday Party Entertainment
  • $250 – $1,200 per event

Kristen J. said “Mike was an absolute highlight of our event. He played beautifully throughout the surprise birthday party and truly elevated the atmosphere for our guests. Our party was a murder mystery theme, and he...”
Featured

Dan Fogel, Pianist

5.0 (6)
4 Verified bookings

  • East Setauket, NY
  • Pianist / Holiday Party Entertainment
  • 17 miles from Fairfield
  • Starts at $350

Catherine L. said “Dan the pianist did a fabulous job playing for us at our annual fundraiser. He handed out cards so people can use their phones with a code to submit a request. He played so many requests from our...”
Featured

Flew The Coupe Cocktails

5.0 (15)
13 Verified bookings

  • South Salem, NY
  • Bartender / Holiday Party Entertainment
  • 18 miles from Fairfield
  • Starts at $150 per hour

Kelly J. said “Tracey was an excellent addition to our party. Professional, knowledgeable, and a great communicator. She helped us craft unique custom cocktails for our guests that provided something for all...”

The Nichols Santa

5.0 (20)
Top Performer
44 Verified bookings

  • Trumbull, CT
  • Santa Claus / Holiday Party Entertainment
  • 8 miles from Fairfield
  • Starts at $150 per hour

Elise S. said “Santa was fabulous! This was our first time doing an event like this at our theatre and he was flexible as we navigated through working through the logistics for the first time. He is prompt,...”

Gomez & Sadlon

4.91 (14)
Top Performer
12 Verified bookings

  • Newtown, CT
  • Jazz Band / Holiday Party Entertainment
  • 19 miles from Fairfield
  • $400 – $1,000 per event

Cheryl A. said “Having background music at our son’s rehearsal dinner was the best idea yet. It added such a nice atmosphere to an already special event. The music provided was varied and pleased everyone’s taste....”

Jazzkwest

1 Verified booking

  • Fairfield, CT
  • Jazz Band / Holiday Party Entertainment
  • Contact for pricing

JAZZKWEST is a Long Established San Francisco Bay Area Quartet Celebrating the Classic American Songbooks of the 1930’s, 40’s and Beyond. Rebekah...

Marc McPherson

1 Verified booking

  • Bridgeport, CT
  • Pianist / Holiday Party Entertainment
  • 5 miles from Fairfield
  • Contact for pricing

I offer versatile live and original music services for any occasion. Whether you need a flawless solo performance, a tight, high-energy band, or original...

Matt Ralabate

2 Verified bookings

  • Stratford, CT
  • Bartender / Holiday Party Entertainment
  • 7 miles from Fairfield
  • Contact for pricing

I started bartending in 2003. I spent 5 years working in varied establishments and then another 6 working private parties. I now exclusively work private...

Bartender Private

5.0 (1)
2 Verified bookings

  • Norwalk, CT
  • Bartender / Holiday Party Entertainment
  • 8 miles from Fairfield
  • $100 per hour

Thomas S. said “Everyone had a great time thanks in part to Luis! Highly recommend. Very personable, skilled and knowledgeable. Great communication. ”

JLS Bartending & Special Events

5.0 (13)
34 Verified bookings

  • Norwalk, CT
  • Bartender / Holiday Party Entertainment
  • 8 miles from Fairfield
  • Contact for pricing

Annette U. said “Thanks to Jessica for all of your help for our 3/23 event! Thanks for coming early, bringing the supplies we requested, getting everything set-up, being friendly & helpful while bartending for our...”

Santa Mike Tolla

5.0 (8)
12 Verified bookings

  • Norwalk, CT
  • Santa Claus / Holiday Party Entertainment
  • 8 miles from Fairfield
  • Contact for pricing

Kate B. said “He was wonderful. Great experience all around. Our event had a very short lead time and he was responsive, accommodating, helpful and very communicative. We genuinely appreciated his expertise and...”

Daniel Slugoski

5.0 (1)
1 Verified booking

  • Milford, CT
  • Pianist / Holiday Party Entertainment
  • 12 miles from Fairfield
  • $100 per event

Chad F. said “Daniel was TOP NOTCH! Professional, courteous, friendly, and willing to play longer throughout dinner. Already excited to book him for our next event!!”

Marc Weissman

4.69 (4)
6 Verified bookings

  • Shelton, CT
  • Pianist / Holiday Party Entertainment
  • 15 miles from Fairfield
  • Contact for pricing

Ardita I. said “The team at Crowne Plaza Danbury cannot thank Marc enough for his services this Easter! Although our booking was close to last minute, Marc was quick with his responses and attentive to our needs....”

Celtic Magic

4.94 (11)
2 Verified bookings

  • Orange, CT
  • Magician / Holiday Party Entertainment
  • 15 miles from Fairfield
  • $600 – $10,000 per event

Ronnie G. said “Daniel and Bella were a fantastic edition to our Fire & Ice Festival at Two Roads Brewing Co. Not only did they put on an exceptional show that kept the crowd engaged, children mesmerized, and adults...”

Rio Bound

1 Verified booking

  • Stamford, CT
  • Jazz Band / Holiday Party Entertainment
  • 16 miles from Fairfield
  • Contact for pricing

We provide both classic Brazilian and Jazz Standards. The Brazilian band plays joyful, uplifting, fun music that everyone LOVES. The jazz band is swinging...

Santa Mike

1 Verified booking

  • Stamford, CT
  • Santa Claus / Holiday Party Entertainment
  • 16 miles from Fairfield
  • $200 – $500 per hour

I am a professional REAL BEARDED Santa Claus with over 5 years experience, including big box stores, in home private parties and corporate events. Along with my...

Dorian James Entertainment

5.0 (2)
2 Verified bookings

  • Stony Brook, NY
  • Classical Ensemble / Holiday Party Entertainment
  • 16 miles from Fairfield
  • Contact for pricing

Alina said “The magician came on time. Very professional. Everyone enjoyed him even adults.”

The Kazi McCoy Jazz Band

1 Verified booking

  • East Setauket, NY
  • Jazz Band / Holiday Party Entertainment
  • 17 miles from Fairfield
  • Starts at $600

Your event deserves a soundtrack as unique as your guest list. We specialize in tailoring live jazz experiences to perfectly fit your atmosphere. Whether you...

Mystique Magic Company

5.0 (27)
21 Verified bookings

  • Ansonia, CT
  • Magician / Holiday Party Entertainment
  • 17 miles from Fairfield
  • $295 per event

Michael M. said “Jeffrey Williams performed for our dad’s, granddad’s, god’s 90th birthday party. He had a repertoire that engaged everyone from the man of honor himself to his youngest great grand child. Thank you...”

Orion Music Ensembles

5.0 (1)
1 Verified booking

  • Bethel, CT
  • Classical Ensemble / Holiday Party Entertainment
  • 18 miles from Fairfield
  • Starts at $400

Phil M. said “We hired a string duo to play Christmas music following our Christmas Eve Candlelight Service. They were excellent musicians, and completely professional. Beryl was very communicative and organized,...”

  • East Northport, NY
  • Magician / Holiday Party Entertainment
  • 19 miles from Fairfield
  • Starts at $250

Kerri said “Our kids aged from 4-8 loved the silly magician! He kept everyone entertained and made sure all the kids were included in the show. He came early and was easy to communicate with! I would definitely...”

Smart Car Santa

5.0 (22)
31 Verified bookings

  • West Haven, CT
  • Santa Claus / Holiday Party Entertainment
  • 19 miles from Fairfield
  • Contact for pricing

Maria C. said “Our experience with Smart Car Santa was wonderful. He was engaging and very kind with our guests, specially with the children. The reading of a Christmas story, allowing the children to participate...”

Chay - pronounced (Chay)

5.0 (7)
10 Verified bookings

  • West Haven, CT
  • Waitstaff / Holiday Party Entertainment
  • 19 miles from Fairfield
  • Starts at $200

Scott A. said “Super nice and happy to have her again! ”

  • Fairfield, CT
  • Bartender / Holiday Party Entertainment
  • Contact for pricing

Flutes & Foam is a luxury mobile bar experience serving Fairfield County and beyond. We specialize in beautifully curated, high-end beverage service—from...

  • Westport, CT
  • Jazz Band / Holiday Party Entertainment
  • 5 miles from Fairfield
  • Starts at $400

Looking to spice up an event with live music? Core Four Jazz featuring Sarah Ferro is available for private parties, holiday events, cocktail receptions,...

On The Count of Two

New member

  • Weston, CT
  • Jazz Band / Holiday Party Entertainment
  • 7 miles from Fairfield
  • Contact for pricing

I provide high-quality jazz through my band On The Count of Two! I can perform in a solo, Duo, trio, or quartet. I am very passionate about music and I love...

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About booking Holiday Party Entertainment in Fairfield, CT

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 Fairfield, Connecticut 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 Fairfield 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 Fairfield, CT area

These Holiday Party Entertainment serve the wider Fairfield and Fairfield county area and travel to Southport, Greens Farms, Bridgeport, Westport, Stratford, Weston, Trumbull, Norwalk, Easton, Wilton, Rowayton, Darien, Redding Ridge, Milford, Georgetown, New Canaan, Redding, Redding Center, Monroe, Shelton, Lewisboro, Woodmont, Derby, Botsford, Orange, Stamford, Ridgefield, Fort Salonga, Stony Brook, and Port Jefferson.

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