Guesthouses is a locally owned vacation rental company, located in Charlottesville Virginia, offering short-term and extended stay rental services. Originally founded in 1976, Guesthouses was once described by a local paper in 1983 as "the oldest guesthouse service in The United States" -- long before Airbnb was even an idea! Today, we manage ~60 properties in the greater Charlottesville area and offer an array of rental options: everything from 1 bedroom apartments, an 8 bedroom boutique hotel on the Downtown Mall to historic country estates in the heart of Virginia's wine country. No matter what brings you to our beautiful town, chances are we have a great option to fit your needs.

New Listing! Spacious, family-friendly home in an excellent location for your next Charlottesville getaway. This 3 bed, 2 bath house is located on a quiet street in the Belmont neighborhood conveniently close to the Downtown Mall, UVA Grounds and I-64 for quick access to the areas vibrant attractions and wineries. Start your mornings with the sunrise over Carter's mountain while gallery-white walls and a lovingly curated collection of original contemporary African art leave you energized and inspired. Furnished to welcome couples and families with children alike, your Charlottesville stay will be worry free! If you can't completely leave work behind, a fully equipped office space for two will make telework a breeze.  Renewing green welcomes guests at the door and signals the start of your stay. The main level of the home offers spaces for gathering with a large family room sectional (plus sleepers sofa), dining table for eight, plus kid's table! The open concept kitchen keeps everyone together with space for many cooks. Through the dining room glass doors, guests will enjoy outdoor patio seating plus a propane grill. Office space for two is just off the kitchen as well as a powder room. Up the stairs on the second floor, guests will find the Primary bedroom with King bed, private balcony, and dual-sink vanity bathroom with separate shower and tub. This level has two additional bedrooms, a second King bedroom and Twin bedroom with two twins, that share a second full bathroom. There is also a laundry closet on this level that guests may use. The top, third floor is a generous flex space with a large sectional, TV and room for play.  The homes gallery-white walls are the perfect backdrop for an incredible collection of primarily East African paintings.