Charlottesville Vacation Rentals


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Centrally located in the beautiful foothills of the Blue Ridge Mountains, Charlottesville is home to historic landmarks and the University of Virginia, not to mention top rated wineries, restaurants and local musical talent and artists.

We've curated the top places to stay in Charlottesville for the best vacation rental experience. Here's a review of the company and profile of their local expert.

Stay Charlottesville

Price Range
Historic Properties
Concierge Services

The 100 Collection of Stay Charlottesville

Gorgeously unique homes with professional interior design, Travis’s collection boasts a mixture of carriage houses, urban lofts, and sprawling estates. Guests can look forward to discovering as many fun curiosities inside these properties as they outside in the landscaped gardens. Each property offers the creature comforts of home without the clutter. From vinyl records to rare coffee table books, to sundials and water fountains, only the most appropriate and perfect items make it into these well-curated homes.

River  Meadows Farm
Friends out at a wine tour
Services Offered
High End LinensHigh End Linens
Concierge ServicesConcierge Services
  • 24-hour live support
  • Dining and Shopping recommendations
  • Curated itineraries
Services Available
  • World-class culinary talent
  • Mercedes shuttle service
  • Local maintenance teams
  • On-property massages
  • Vineyard trail rides
  • Metropolitan Hall venue bookings
  • Wine tours
Doyen of Stay Charlottesville
Profile picture for Travis Wilburn
Travis Wilburn
Owner and Founder
Favorite Restaurants
Mas, Oakhart Social, Bebedero
Favorite Wineries
Pippin Hill, King Family Vineyards, Jefferson Vineyards, Veritas, Afton Mountain Vineyards
Favorite Coffee Shop
Grit Coffee
Best place to relax
Rockfish Ranch
Best place to go out
Fitzroy, Downtown Belmont

Travis Wilburn started out his hospitality business by building a guest house towards the east end of his primary residence. He started renting it on Craigslist, and then eventually acquired several other properties. When he began to manage other owner’s homes, he would go out and meet each one individually. Travis wanted to look them in the eye and shake their hand. He wanted them to know that he was a local and would care for their property as if it was his own.