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Drew Thomasson


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.