Pool House at Waterperry Farm

Welcome To Stay Charlottesville

What We Offer Is Unique

Welcome to Stay Charlottesville

We offer our guests the ability to stay in the area’s finest carriage houses, apartments, historic homes and estates, whether it is for two nights or two months. We offer all the amenities of a hotel, but with the privacy and convenience of a local home. Stay is very selective of the properties we choose to manage, so that we can surpass your expectations.

Reserve a property now online or call 434-977-0442 to get started. We want to help you experience Charlottesville and the surrounding areas like a local and can help you plan your trip to our area, including the services below.

The One Hundred Collection Vacation Rental Properties Seal

THE 100 Collection

Peer Reviewed Properties Representing an International Collection

Walking on the Bricks of the downtown mall charlottesville

Downtown District

Charlottesville city properties close to the Downtown Mall, Belmont neighborhood, or University area

Modern pool at Charlottesville Vacation Rental

Properties with a Pool

Vacation rentals with a pool. Great for a hot day

Arial view of Ben Coolyn Farm

Farms & Estates

Large farm and estate properties located in Charlottesville and the surrounding area

Living room in Charlottesville Vacation rental.

UVA & Surrounding

Properties that are generally in neighborhoods bordering UVA or within a short drive to the University

Secluded Cabin rental in central virginia

Cottages & Retreats

Perfect to get away from it all, these properties surround the Charlottesville area

Pool House View at Waterperry Farm

Virginia Countryside

Properties that are located outside of Charlottesville with bucolic views

Hotel Amenities in Charlottesville Vacation Rental


Boutique hotels close to UVA and the historic downtown mall

Vineyard Views in Central Virginia.

Vineyard Properties

Properties on or near popular vineyards on the Monticello Wine Trail

Afton Mountain Fireplace.

New Properties

Our newest properties in the Charlottesville, Albemarle County, and Nelson County areas

Modern kitchen in Charlottesville Vacation Rental

Monthly/Long Term Rentals

Long term and monthly rentals in Charlottesville VA. Apartments, executive suites, and cottages

Dog Friendly Vacation Rentals in Charlottesville

Properties Allowing Dogs

Looking to bring your furry friend along? These properties are great choices


For a list of other services we can arrange for you, please visit our Guest Services page.

Chef setting plates for private chef event.


From Private Chefs to yoga right at your vacation rental, our concierge can help customize your stay!

Vineyard Vacation Rental - Couple enjoying glass of wine.

Wine Tours

Offering free pickup from Wintergreen and the Downtown Mall, Monticello Wine Tours offers private wine tours along the Monticello Wine Trail. 

Wedding on the Bricks of the Downtown Mall

Old Metropolitan Hall

OMH is the perfect venue for everything from corporate lunches and meetings to rehearsal dinners and intimate weddings, located conveniently on Charlottesville’s downtown mall.

Front Desk tat the Common House Charlottesville


As a special perk to Stay Charlottesville guests, stop into Common House on the downtown mall to experience the amazing space they have created.

Massage at Waterperry Farm


Book a massage in the privacy of your vacation rental from the best massage therapists in Charlottesville.

Horseback Riding at Afton Mountain Vineyards

Vineyard Trail Rides

Our partners offer scenic horseback trail rides through beautiful Vineyards with a short break for tastings.