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Guesthouses

Fifty Years, Nearly 100 Homes

Virginia Guesthouses™ has been 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

Virginia 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 would say Guesthouses™ was the first vacation rental company in the U.S. Fifty years later, we still connect guests with authentic Charlottesville 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 nearly 100 properties across Charlottesville, the Blue Ridge foothills, and Nelson County. 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

Culture, Wine & UVA

Charlottesville

Over 50 homes. Walk to the Downtown Mall, catch a UVA game, or reach a dozen wineries in fifteen minutes.

Crozet

Small Town, Mountain Views

Crozet

Just west of Charlottesville. Bold Rock cidery nearby, Blue Ridge views from most porches, good for families.

Keswick

Horse Country & Rolling Estates

Keswick

Split-rail fences, open pasture, and homes set well back from the road. Larger properties on very quiet roads.

Nellysford

Blue Ridge & the Upper James

Nellysford

Close to the upper James River and Wintergreen Resort. Quiet roads, orchards, and our most secluded homes.

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