Braeside Annex | Mountain Views Close to Boars Head & UVA

We're Guesthouses, a Virginia-based vacation rental management company with deep roots in the community. Founded in 1976, we're proud to be the oldest and most established vacation rental company in the area, with decades of experience caring for homes and hosting guests.

We manage each property as if it were our own, working closely with homeowners and focusing on what truly matters to guests: clean and comfortable spaces, thoughtful details, clear communication, and responsive local support. Our long-standing presence means we know these homes, these neighborhoods, and this region exceptionally well.

Whether you're here for a relaxing getaway, a family visit, or a special occasion, our goal is to provide a seamless, welcoming stay and genuine hospitality from start to finish. We're local, available, and always happy to share recommendations or assist with anything you need to make the most of your time here.

We look forward to hosting you and helping you unlock, explore, and enjoy everything the area has to offer.