Skip to content
Guesthouses

Fifty Years of Hospitality

Hosting guests of Central Virginia since 1976
Newspaper article from The Cavalier Daily, April 5, 1985, about bed and breakfast lodging with illustrated header showing a country house

Our Story

Founded in 1976, Before the Concept Existed

Guesthouses™ was created when four women saw that travelers wanted more personalized, comfortable stays than large hotels could provide. They brought the bed & breakfast concept to the United States at a pivotal moment before Airbnb or short-term rentals were mainstream. Some say Guesthouses™ was the first vacation rental company in the United States. Fifty years and nearly 100 properties later, we still connect guests with authentic Virginia experiences and homeowners with the opportunity to share their homes.

Our History

Fifty Years in the Making

In 1976, Sally Reger and three colleagues set out to give travelers something hotels couldn't: a real home, in a real neighborhood, with someone who actually knew the area. That idea grew into Virginia Guesthouses™ today with nearly 100 properties that range from Charlottesville downtown hotels to Crozet vineyard stays to Nelson County accommodations. Each property is managed the same way we started, with a local team focused on care for the guest and respect for the home.

Vacation Rentals in Central Virginia

Where Our Properties Are Located

Charlottesville

Dining, UVA, & History

Charlottesville

An array of possibilities, from boutique hotels on the Downtown Mall to homes close to UVA. Stay close to the Downtown Mall, catch a UVA game, or explore historical sites.

Crozet

Vineyards & Mountain Views

Crozet

Just west of Charlottesville and 20 minutes to UVA, this town is situated in the foothills of the Blue Ridge. It's home to apple and peach orchards and some of the region's best vineyards.

Keswick

Horse Country & Rolling Estates

Keswick

East of Charlottesville and 1 hour to Richmond featuring equestrian activities, rolling hills, and well-appointed homes on gorgeous acreage. Close to vineyards and 20 minutes to UVA.

Nelson County

The Adventurer's Haven

Nelson County

Truly at the base of the Blue Ridge Mountains with easy access to Shenandoah National Park, Virginia Route 151 Craft Beverage Trail, and Wintergreen ski resort.

What We Do

Nearly 100 Properties Across Central Virginia

Aerial view of yellow farmhouse with metal roof surrounded by dense forest, mountains, and distant red-roofed house at dusk

Vacation Rentals & Inns

Homes, cottages, and boutique properties for every kind of traveler.

  • Pet-friendly options available

  • Extended stays and short-term rentals

  • Hotels and suites in town

Dining table with three chairs facing large windows overlooking green mountains and blue sky with clouds

Local Expertise

We know Charlottesville and the surrounding region deeply.

  • Help with weddings and events

  • UVA visitor accommodations

  • Shenandoah and Blue Ridge access

Open-plan living room and kitchen with exposed wood beams, bar seating, built-in shelving, and hardwood floors.

Real People, Real Service

Guests tell us they value speaking with a real person when booking.

  • Personal guidance on the right fit

  • Fifty years of hospitality experience

  • Homeowner property management services