Our Guesthouses' History

Since 1976


 Created in 1976, Guesthouses Reservation Services in Charlottesville, Virginia emerged at a pivotal time in the hospitality industry where travellers wanted a more personalized and comfortable stay wherever they travelled. The bed & breakfast was a largely European phenomenon before this time and Guesthouses sought to bring this type of travel to the United States. With the announcement of the Queen Elizabeth of England’s trip to Charlottesville, Guesthouses Reservation Services was born to accommodate all the tourists funnelling into the city to set eyes on the Queen. It was a roaring success in Charlottesville and gave visitors a peak into how the locals lived and gave homeowners a chance to showcase their homes and provide exceptional experiences. Newspaper and magazines all over the country (USA Today, Travel & Leisure, Virginia Pilot), all saw the benefits of this new phenomenon of Bed and Breakfast accomodations.

Guesthouses was started by four women who saw this need for change in the hospitality business long before the times of AirBnB! Guesthouses was the first of its type in the country. The motto of "Guesthouses is YOU and works for you" still stands today with Rachel Penny (Darden MBA) as the fourth woman to own it over its forty year of ownership. Guesthouses historical, and current, aim is provide guests with a true authentic Charlottesville experience and home that differentiates itself from the traditional hotel.

From 1986-2006, Mary Hill and Bernard Caperton owned the company and championed the B&B cause in both the state of Virginia and beyond. Their own home off of Preston Place in downtown Charlottesville was Thomas Jefferson's desired location for the home of the University of Virginia. Kelly refused to sell it to him because of his distate for Jefferson's politics, but instead used the home as a slave quarters for his 500-acre farm. Times changed over the 150 plus years, but the bones of the home remained the same as the Capertons sought to preserve the space. Investing heavily in a gorgoues "Alice in Wonderland" type garden, guests still call today asking for this amazing home. The property is under new ownership.

Rachel Penny bought the company in 2016 and saw the unique selling point of the traditional Guesthouses model. Former owner Joyce said this of Rachel: “I couldn't have found a better owner, now rooted in the community and with a passion for hospitality industry, to continue the legacy that Guesthouses has built.” As a graduate of Darden and with a background in marketing, she introduced her skills to take the company to the next level. She created a website so visitors could start to book online versus over the phone; however, the personal touch is not lost. Guesthouses is stil here for YOU and will continue to be as we thrive for excellence.

 Quotes from the Archives

“It is not alway so important for a breakfast to be “full” as it is to make it interesting: having fresh ingredients-- fresh fruit, a fresh pot of coffee, and croissants or home-made muffins. The way breakfast is served is important: try to make it an elegant, fun way for the guests to start their day” -October 25, 1985 Newsletter

“Guest especially appreciate: *Real coffee (not instant)--a percolator is a small investment well worth the money...Besides, America is heavily into nutrition these days, and some regard soft white bread as a sin.” -Newsletter




Newspaper clipping for Guesthouses

Guesthouses has been women-owned for it’s entire history. Rachel Penny, the current owner, continues to support women in business and other empowering roles. Guesthouses is also a certified member of the Department of Small Business and Supplier Diversity, which seeks to promote minority-owned businesses in our nation.