Who We Are

Drew Thomasson - Director of Operations
A native of Virginia, Drew returned to his home state in 2016 after spending five years spending time in Colorado where he became an expert in downhill skiing, igloo building, and caribou riding. Though he doesn't use any of these skills in his current role, his experience running vacation rentals been essential to Stay Charlottesville. As our hospitality and tourism guru, Drew oversees the day-to-day operations and ensures that our properties and service always exceed guests' expectations.   



Kate Farley - Director of Sales/Customer Experience
A long-time local and lover of all things Charlottesville, Kate knows just about everything there is to know about the goings on around town. Whether she's offering restaurant recommendations or filling us in on upcoming events, Kate is always looking for ways to enhance our guests' experience. Kate comes to us from the prestigious Yellowstone Club where she ran the concierge program for the private membership. 



Anna Quillon - Operations & Logistics Coordinator
Known to many as Instagram's "The Hometown Tourist", Anna brings her enthusiasm for living local to her role as Operations & Logistics Coordinator. Anna has a knack for working with our guests to create an experience that is tailored to their taste. Also a winner of a 2015 Charlottesville Albemarle Tourism Recognition Award, Anna truly excels at customer service. When she's not with working for us, she's out adventuring somewhere, doing something blog-worthy. 




Andrea Hubbell - Architectural Photographer
Andrea is a Charlottesville-based commercial photographer specializing in architectural, lifestyle, + culinary imagery. Her education and experience in architectural design have given her an understanding of human interaction with space and an appreciation for composition and detail. Her goal is to always create an evocative representation of the places she photographs and to give the viewer the feeling that they are present in the scene. When not behind a camera, Andrea is busy cooking with her hubby, hiking with her dogs, and designing her parents a house in Florida.



Bill Chapman - CoFounder
Bill Chapman is a Charlottesville native who worked in the media business for 20 years after co-founding the local free weekly paper C-VILLE Weekly. In his spare time he pursues adaptive reuse projects in the local real estate arena. Recently, he opened his 27-room boutique inn in an old boarding house at UVA. When not at one of his many ventures, he sails, cooks, and drives old cars to his kids' lacrosse games.




Travis Wilburn - CoFounder - Managing Partner
When Travis moved to Charlottesville in 2000, he found a perfect marriage for his passion for buildings, music, and art. An architect-at-heart without the ability to draw, he found himself drawn to the historic homes in Charlottesville and the Blue Ridge with no way to work with them. Solution: Stay Charlottesville. Travis continues to bring that same passion with him to Stay Charlottesville every day. True to his fun, competitive nature, he will one day open a 28-room boutique inn, right next to Bill’s.