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423 Holiday Party Entertainers serving Annapolis, MD

Featured

STOOpendous Magic

5.0 (13)
Top Performer
21 Verified bookings

  • Odenton, MD
  • Magician / Holiday Party Entertainment
  • 13 miles from Annapolis
  • $300 and up

Clare H. said “Scott was thoroughly entertaining and kept the audience of young adults guessing. It was a 35th birthday party and the young ones emailed me afterwards and called it the best house party they had... ”
Featured

Geno Marriott & the Spirit of Jazz

5.0 (14)
Top Performer
17 Verified bookings

  • Washington, DC
  • Jazz Band / Holiday Party Entertainment
  • 30 miles from Annapolis
  • $500 - $10,000

Maurice W. said “The singer and band were exceptional. Highly recommend them for your next event. They were timely, professional and flexible. ”
Featured

The Creswell Club

5.0 (31)
Top Performer
41 Verified bookings

  • Washington, DC
  • Jazz Band / Holiday Party Entertainment
  • 30 miles from Annapolis
  • $1,200 and up

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

Louis Pettinelli Entertainment

4.92 (68)
Top Performer
243 Verified bookings

  • Washington, DC
  • Jazz Band / Holiday Party Entertainment
  • 30 miles from Annapolis
  • $300 dollars and up

Kelly S. said “Hired for our corporate event. They did a fantastic job from communication to execution to performance. Thanks! ”
Featured

The Jazz Experience

5.0 (33)
Top Performer
43 Verified bookings

  • Washington, DC
  • Jazz Band / Holiday Party Entertainment
  • 30 miles from Annapolis
  • $200 and up

Wells said “Our guests could not stop raving about our amazing guitar player. Adam showed up early, was totally self-sufficient, and played outstanding music. I would absolutely recommend him to anyone. ”
Featured

Michael Chamberlin, Magician

4.98 (130)
Top Performer
207 Verified bookings

  • Washington, DC
  • Magician / Holiday Party Entertainment
  • 30 miles from Annapolis
  • $300-$6000

Jasmine C. said “This was excellent! I would recommend him 1000%. We can't wait to bring him back. I work in senior living, and our residents truly enjoyed every minute of the show. He was engaging, professional,... ”
Featured

Music By Louis

5.0 (8)
Top Performer
13 Verified bookings

  • Washington, DC
  • Pianist / Holiday Party Entertainment
  • 30 miles from Annapolis
  • $250 and up

Marita F. said “We booked MusicByLouis as a summer performer and our kids had a great time. It was interactive which is perfect for kids. We will book again! ”
Featured

Daniel David - DC's #1 Mentalist Magician

5.0 (11)
Top Performer
14 Verified bookings

  • Washington, DC
  • Magician / Holiday Party Entertainment
  • 30 miles from Annapolis
  • $3,500-$10,000+

Cindy A. said “Dan strolled around the party and kept everyone entertained! We will be inviting him back next year for our Holiday Party! ”
Featured

Charlie Ross Magic

5.0 (2)
Top Performer
6 Verified bookings

  • Washington, DC
  • Magician / Holiday Party Entertainment
  • 30 miles from Annapolis
  • $300-$1000

Nimah G. said “Charlie performed for my husbands small birthday party at home and we all had an amazing time! It was like hanging out with a funny friend who can do amazing tricks. Would highly recommend! ”
Featured

Lillie and the LushTones

5.0 (6)
Top Performer
2 Verified bookings

  • Alexandria, VA
  • Jazz Band / Holiday Party Entertainment
  • 32 miles from Annapolis
  • $200 - $2,500

Teresa H. said “Professional AND with a great sound! We loved having Lillie and the Lushtones at our Annual Fundraiser! Don't miss out on the fun - book them today! ”
Featured

Ruthy Stenger

4.96 (30)
Top Performer
26 Verified bookings

  • Bethesda, MD
  • Pianist / Holiday Party Entertainment
  • 32 miles from Annapolis
  • $400-$800

Judy S. said “Ruthie did a great job at our holiday party, she was energetic and fun ”
Featured

The Masters of Mixology

4.98 (47)
Top Performer
76 Verified bookings

  • Arlington, VA
  • Bartender / Holiday Party Entertainment
  • 33 miles from Annapolis
  • $50-5000

Amanda S. said “Our bartender understood the assignment and delighted our guests! ”
Featured

Don Juan

4.92 (52)
Top Performer
106 Verified bookings

  • Waldorf, MD
  • Magician / Holiday Party Entertainment
  • 33 miles from Annapolis
  • $350 and up

Jacob T. said “We asked Don Juan for a half hour performance on our 8 year old daughter's birthday party and he really delivered! He has fantastic magic tricks and jokes and kept both kids and adults entertained. We... ”
Featured

Magician Kourosh Taie

5.0 (54)
Top Performer
41 Verified bookings

  • McLean, VA
  • Magician / Holiday Party Entertainment
  • 37 miles from Annapolis
  • Contact for rates

Mike D. said “Great show!!! ”
Featured

Dr. Mix-A-Lot, LLC

5.0 (28)
Top Performer
38 Verified bookings

  • Potomac, MD
  • Bartender / Holiday Party Entertainment
  • 39 miles from Annapolis
  • $45/hr + up (gratuity included)

Kathleen W. said “Marianna was wonderful and everyone commented on how friendly she was to them. ”
Featured

Illusions By Vick

4.98 (59)
Top Performer
105 Verified bookings

  • Potomac, MD
  • Magician / Holiday Party Entertainment
  • 39 miles from Annapolis
  • $325 to $1500

Steph B. said “We booked Vick for a Friendsgiving party at my house and he is 10000000% worth every dollar. The show was captivating from beginning to end and all my friends were so astounded by all the elements... ”
Featured

Cityline Band

5.0 (4)
6 Verified bookings

  • Upper Marlboro, MD
  • Jazz Band / Holiday Party Entertainment
  • 18 miles from Annapolis
  • Contact for rates

Arthur W. said “Very prompt. The music was excellent. The band did their thing, and the event loved them. ”
Featured

Refined Mixology LLC

1 Verified booking

  • Upper Marlboro, MD
  • Bartender / Holiday Party Entertainment
  • 18 miles from Annapolis
  • Contact for rates

Refined Mixology offers professional mobile bartending for weddings, private parties, and corporate events. I create high-quality cocktails and mocktails with a...
Featured

Yany’s Cocktails LLC

5.0 (7)
1 Verified booking

  • Hyattsville, MD
  • Bartender / Holiday Party Entertainment
  • 24 miles from Annapolis
  • $350 and up

Rosa S. said “Yany was prompt, and professional the entire evening. She was very accommodating to our guest, kept the buffet line moving efficiently, and cleared the tables promptly. We definitely recommend her... ”
Featured

Santa PoPPoP

5.0 (17)
29 Verified bookings

  • Columbia, MD
  • Santa Claus / Holiday Party Entertainment
  • 25 miles from Annapolis
  • Contact for rates

Pete M. said “He came to our assisted living and was so personal with each child and each resident. We cannot say enough great things about him. We would give him 100 stars if we could. ”
Featured

Santa Tim

5.0 (7)
12 Verified bookings

  • Ellicott City, MD
  • Santa Claus / Holiday Party Entertainment
  • 26 miles from Annapolis
  • $175 and up

India B. said “Mr. Santa Tim was wonderful my kids and I loved him. He read them a story took so many pictures, can’t wait to have him again. ”
Featured

Night & Day Jazz Ensemble

4.87 (13)
22 Verified bookings

  • Silver Spring, MD
  • Jazz Band / Holiday Party Entertainment
  • 29 miles from Annapolis
  • Contact for rates

Jamie C. said “This was the perfect Jazz ensemble for our reception! They were professional, courteous and easy to work with. It's fun to have a jazz singer with the band! The guests loved it! ”
Featured

Morgan Treni & The Golden Estate House Band

5.0 (17)
1 Verified booking

  • Washington, DC
  • Jazz Band / Holiday Party Entertainment
  • 30 miles from Annapolis
  • $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

Mega Magic- Magician Mike D'Urzo

5.0 (22)
23 Verified bookings

  • Washington, DC
  • Magician / Holiday Party Entertainment
  • 30 miles from Annapolis
  • Contact for rates

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

Mixin' Mimi

4.68 (31)
13 Verified bookings

  • Washington, DC
  • Bartender / Holiday Party Entertainment
  • 30 miles from Annapolis
  • Starting at $325

James H. said “Nothing but a great review. Mimi and Marcus killed it. Made our Christmas Eve. Our guest raved about them. Top shelf would recommend to anyone. Great job.😀😀 ”
Featured

SpeechLess

4.98 (21)
2 Verified bookings

  • Washington, DC
  • Jazz Band / Holiday Party Entertainment
  • 30 miles from Annapolis
  • $3,500-25,000

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

The Wright People

5.0 (6)
10 Verified bookings

  • Washington, DC
  • Waitstaff / Holiday Party Entertainment
  • 30 miles from Annapolis
  • Contact for rates

Vik said “Great setvice ”
Featured

Harrison Jazz Ensemble

4.70 (28)
56 Verified bookings

  • Washington, DC
  • Jazz Band / Holiday Party Entertainment
  • 30 miles from Annapolis
  • $1000-2500

Katy M. said “We were so happy with booking the Harrison Jazz Ensemble made up of Tim Ford on drums/percussion, Chris Smith on Bass, and Ben Allen on piano. Every person watching was full of smiles and was loving... ”
Featured

Great Wayne Productions

5.0 (2)
1 Verified booking

  • Fort Washington, MD
  • Pianist / Holiday Party Entertainment
  • 34 miles from Annapolis
  • $600-2000

Eddie D. said “Great Wayne Productions delivered an outstanding experience from start to finish. Their professionalism, creativity, attention to detail, and commitment to excellence truly stood out throughout the... ”
Featured

Cognac Jazz

5.0 (4)
4 Verified bookings

  • McLean, VA
  • Jazz Band / Holiday Party Entertainment
  • 37 miles from Annapolis
  • $700 to $5000

Kirti K. said “Band lead, Steve, was incredibly communicative prior to booking the event, and also after booking. The day of, all band members arrived in a timely manner, were professionally dressed and played a... ”
Featured

Lore Salad

4.84 (124)
236 Verified bookings

  • Falls Church, VA
  • Waitstaff / Holiday Party Entertainment
  • 37 miles from Annapolis
  • Contact for rates

Kate C. said “We reached out for help only a week before our event and Lore was able to provide a great waitstaff. Our waitstaff showed up on time, was helpful throughout, and completed everything we discussed... ”

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About booking Holiday Party Entertainment in Annapolis, MD

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 Annapolis, Maryland 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 Annapolis 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 Annapolis, MD area

These Holiday Party Entertainment serve the wider Annapolis and Anne Arundel county area and travel to Parole, Arnold, Foxmoor, Edgewater, Riva, Mayo, Herald Harbor, Crownsville, Severna Park, Gibson Island, Davidsonville, Arden on the Severn, Lake Shore, Shady Side, Stevensville, Galesville, Pasadena, Millersville, Harwood, West River, Crofton, Chester, Gambrills, Lothian, Churchton, Riviera Beach, Odenton, Deale, Glen Burnie, and Tracys Landing.

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