Meet the Guesthouses Team

At Guesthouses we're passionate about sharing the unique and wonderful areas and events in our community here in Charlottesville, VA. Each member of our team, as well as each of our homeowners, have intimate knowledge of what makes a vacation rental stay special. Meet the team behind the scenes of your uniquely curated stays. 

Drew Thomasson - Owner of Guesthouses

As a Charlottesvillian native, Drew feels compelled to be a steward for the continual growth of the Charlottesville community. As for taking on this responsibility, he started Cvillas and Estates to offer guests the service values of the true Charlottesville way: Genuine. Quality. Innovative.


Drew has been in the short-term vacation rental industry since the beginning of 2015 when he joined Natural Retreats at their Charlottesville headquarters to help start their Homeowner Relations Team during an aggressive expansion period.  Soon after joining Natural Retreats, he was relocated to Denver, CO to help open their western territories office. 


After two years with Natural Retreats, he moved back to Virginia where he joined a local short-term rental company as their General Manager. Drew is excited to now lead Guesthouses, keeping the Guesthouses charm and adding innovation to further its core values. Drew lives in town with his wife, Annie, their two children, and dog, Willy.

Tim - Operations Specialist

Tim has called several cities home in his lifetime, but has become a real Charlottesville local. After years of showing off Charlottesville from atop Carter's Mountain, he is now welcoming guests from down below. Tim keeps the day-to-day running smoothly and puts the final touches on spaces before guests arrive. When he's off duty, Tim can be found playing bass with his band, painting, or writing. 

Amberly - Marketing and Reservations Manager

A Virginia native, Amberly has spent the last 10 years in Charlottesville and joined Guesthouses so she could share this special city with others. She is an outdoor enthusiast and always has recommendations for local trails and après-ski. She's usually the voice on the other end of the line when you contact Guesthouses and is always ready to help!

Karen - Reservation Specialist

Karen relocated to Charlottesville over 20 years ago and serves the children of our communiy as a dedicated high school science teacher. She is "stretching her wings" in a part-time role with Guesthouses, learning new things about her beloved town. Karen is a real problem-solver and a resource for guests especially after-hours.

Will -Operations Manager

Having grown-up in Charlottesville, Will has all kinds of insider knowledge to share. He joined Guesthouse in 2021 and was the first designated "boots on the ground" team member. Now, he helps run the behind the scenes pieces of the puzzle like coordinting our cleaning team, vendors, and supply orders.