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Guest Reviews ( view all )

"This was our first time spending a weekend in any type of a vacation rental and we can't wait to do it again! Thank you!"
---Rita Morgan, Miami, FL
"I would recommend to anyone considering a visit to the Charlottesville area to stay at this property. Not only is it extremely comforta..."
---Christine
"Just a note to tell you how much we enjoyed our stay at Point Lookout!! The accommodations were just fine, the TV worked great, I could..."
---Jurgen
"Everything went great, we really loved the house and the location was just perfect. We had a chance to visit a lot of the local wineri..."
---Shannon
"With Jakes help my husband & I reserved for 2 nts. in Oct. while visiting with family nearby the Belmont Guest House. We knew we wante..."
---Llyod N
"We enjoyed the stay. We liked the location and the property was excellent. We would use your service again."
---Bill
"We enjoyed staying at the Tree House unit on First Street in Charlottesville. It was walking distance to the shops and restaurants dow..."
---Amanda
"We loved our stay in the house. The beds were VERY comfortable and it was nice to have the big sectional couch to watch TV as a family ..."
---Karen
"This was our second time at a Stay Charlottesville property, and both stays were great. The Rutledge home is beautiful, spacious, and c..."
---Lisa
"After 3 years of staying at hotel chains in Charlottesville, we just had the best visit ever staying at Walker Square!"
---Rick and Beth N.
"It was great. We really just needed a quick night away and this did the trick. The room was nice and well maintained. Thank you."
---Amanda
"We thoroughly enjoyed staying at the guest house. The neighborhood was nice and quiet and close to downtown and the shops/restaurants i..."
---Dan



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Charlottesville Vacation Rentals

Welcome to Stay

We offer our guests the ability to stay in the area’s finest carriage houses, apartments, historic homes and estates whether it be for two nights or two months. Our homes host everyone from the bride and groom, to the explorer of Virginia’s wines and brews, to the executive who is tired of the experience of living in a hotel, or just someone trying to find a new home. We’re proud to be of service.

Reserve a property now or call 434-977-0442 to get started. Have a question or if you need to find a property close to a specific event, check out our map of properties available. 

Why Stay?

To experience Charlottesville like a local. While hotels offer certain standards — clean linens, a bed, a TV, towels, soap, standard furnishings and expectations that can be found here or there — what Stay offers is unique. No two properties are the same. While we offer all the amenities of a hotel, we also offer privacy and convenience of a local home. And no tricky homeowner communications. We take care of all that. With Stay, what you see is what you get. No hassles and no worries. When you book one of our properties, its yours.

Charming Properties

You’ll find yourself in some of Charlottesville’s most charming city neighborhoods, on a nearby bucolic farm, or on a mountain overlooking a valley. Stay is very selective in the properties we choose to manage so we can surpass your expectations. We choose our properties based on location, design, and details. You'll find exposed beams, a tasteful mix of vintage and modern furnishings, local art hanging over the mantel, wine glasses in the cabinet — and your friends & family relaxing in the living room. We offer you a home in our hometown.

How to get Started:

Ask yourself, where do I want to stay? We offer a variety of categories:

Need help? Give us a call: 434-977-0442.  We'll you get situated. Meet the team

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Old Metropolitan Hall is Stay Charlottesville's premier private event space in the heart of downtown Charlottesville. We have thoughtfully restored one of Charlottesville's beloved historic buildings. Old Met is comprised of two floors: an open, elegant ballroom featuring beautiful wood flooring, original tin ceiling tiles, and era-inspired chandeliers and a more intimate bar area designed with copper countertops, exposed beams and bricks, and a black and white diamond flooring. Old Metropolitan Hall is the ideal location for your wedding reception, rehearsal dinner, gala, fundraiser, corporate lunch, or special celebration. Visit our website or call 434-260-7144 for more information.