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Jessica Jester

Reservations Specialist/Guest Relations

Jessica was born and raised on Chincoteague Island, Virginia. In 2006 she moved to Virginia Beach, Virginia and found her love and passion for the hospitality industry. After being away from her hometown for ten years, she was ready to come home. Like most islanders, she has that “marsh mud between her toes” and was ready get back to her Eastern Shore roots.

Susan Lewis

Reservations/Homeowner Accounting

Susan was born and raised on the Eastern Shore of Virginia and lives just a few minutes from Chincoteague Island.  She has grown up among the locals, visitors, and ponies, and has developed a true love for the island.  When she's not in the office, you can find her hanging out with her adorable, spoiled dog named Hemi, in the kitchen baking and decorating delicious specialty cakes, horseb

Kayla Lenhoff

Reservations Specialist

Kayla was born in Alexandria, Virginia but she moved to Chincoteague in 2005 and has lived on the island ever since. She loves the island and everything it has to offer and cannot imagine living anywhere else. She has over 10 years experience in the local service industry and is very proud to have become a Chincoteague Resort team member.

Jackie Tripp

Jackie Tripp

Housekeeping Director

Jackie was born and raised on the Eastern Shore of Virginia, and spent most of her childhood growing up on the Island. She has been married for 25 years to her husband, George, and they are very proud parents to four children (Brandon, William, Kamryn and Landon). In her free time she likes to plan her next family cruise to the Caribbean! 

Megan Wallace

Marketing/Housekeeping Support

Megan was born and raised on the Eastern Shore of Virginia and has been coming to Chincoteague her whole life. She loved the island so much that she finally decided to move here in 2015. A 2017 honor graduate of University of Maryland Eastern Shore, Megan found her home with Chincoteague Resort Vacations shortly afterwards.

Dawn Wharton

Maintenance Department

Dawn was born and raised in a small town on the Eastern Shore of Virginia. She loves the country life and everything that comes along with it. There is nothing better than the smell of freshly cut grass and the fields of manure! In January 2017, after 17 years at her previous job, Dawn took a leap of faith and joined the team at Chincoteague Resort Vacations.


Charlie Clarkson

Maintenance Department

Charlie was born and raised in Baltimore, Maryland. His grandfather, "pop", had a family vacation home on Chincoteague, which the family would visit every summer and holidays during his childhood. Charlie bounced back and forth between Baltimore and Chincoteague before the island became his home in 1993.

Nicolette Hickman

Nicolette Hickman

Operations Accounting

Nicolette was born in NY and relocated to the wonderful small town of Chincoteague Island during her young elementary years. As a 3rd generation property manager (grandmother, mother, and now herself), it was only natural that after graduating high school she continued her education in the Real Estate field.