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 Charlottesvillian native, naturally Drew feels the necessary obligation to being good stewards towards the continual growth of the Charlottesville community. As for taking on this responsibility, he started Cvillas and Estates to offer guests of the town, homeowners new and old the service values of the true Charlottesville way: Genuine. Quality. Innovative.

Drew was born and raised here in Charlottesville and 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 the inovation to further the core values. Drew lives in town with his wife, Annie, and dog, Willy. They will be expecting their first child, Lucy (Future Guesthouses Legacy :) ) in December!

Owner of Guesthouses

Ashley Reid

General Manager 

Ashley is from the Outer Banks of North Carolina, where she was born and raised. After high school, she went to College of the Albemarle focusing her studies on business and working in the property management industry.


After a year of schooling in her hometown, she spent two years in Wilmington, NC, furthering her education in business before she returned to the Outer Banks to pursue her interest in wedding photography, eventually becoming owner of Island Photography.


She continued her working in the property management industry, for Shoreline OBX Vacation Rentals working her way up to Marketing Director. After years of living at the beach, the mountains were calling her name and she now resides in Charlottesville with her fiancé Myles, loving mountain and city life!

General Manager