Who We Are

Stay Wintergreen is a member of the STAY family of properties. Our management team and staff are all local to the area and can help plan your visit beforehand, as well as assist in unexpected issues during your stay, ensuring that your visit will be an extraordinary experience.

The Stay Management Group was founded in 2011 by Travis Wilburn and Bill Chapman in Charlottesville, VA as Stay Charlottesville. Wilburn and Chapman wanted visitors to the city to have the opportunity to live like a local, while still enjoying a world-class vacation. This meant introducing guests to the finest homes of the area for their stay, as well as helping them to discover other best in class tourism partners. Realizing that this made sense for other wonderful and unique locations, Stay began to expand and bring its motto of ‘exceptional local experiences’ to other areas.

Stay continues to grow and is proud to have Stay Wintergreen as part of our vacation rentals family.