• custimages/slide1.jpg

  • custimages/slide2.jpg

  • custimages/slide3.jpg

  • custimages/slide4.jpg

  • custimages/slide5.jpg

  • custimages/slide6.jpg

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
"My boyfriend and I decided to pass through Charlottesville at the end of our winter break and could not have been happier with this hom..."
---Passing through Cville
"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



Like Stay,
Today!
flipkey

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 looking for the Virginia Wine and Brew tour down the Nelson 151, to the executive who is tired of the experience of living in a hotel, to 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 location, 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, and standard furnishings — 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, it's 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 of the properties we choose to manage so that 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.

We are pleased to be offer package deals to our guests when using one of our sister companies. For more information, please call the Stay Charlottesville offices. 

Charlottesville_Vacation_Rental.jpg

Monticello Wine Tour and Coach Company is Stay Charlottesville's newest addition. Whether you are looking for a local wine tour, event or wedding transportation, executive travel, or an airport transfer, Monticello Wine Tour & Coach Company is prepared to take you. Personal and professional with one of the most modern fleets in the area, MWTCC will cater to your plans by pairing our experience and familiarity with the area with your desire for an effortless and enjoyable experience. 

Charlottesville_Vacation_Rental.jpg

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 comprises two floors: an open, elegant ballroom featuring beautiful wood flooring, original tin ceiling tiles, and era-inspired chandeliers and downstairs, boasts 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.