House holiday rentals in Orange County

The Ranch at Wine Country - Complimentary bottle

Welcome to The Ranch at Wine Country located in the heart of charming historic Gordonsville, VA. The Ranch provides all the essential amenities (condiments, tea & coffee, blow dryer, towels & much more) and some to enjoy your time away whether it be for work or play! The Ranch is pet friendly w/ a large comfy dog bed and water & food bowls. The Ranch is just minutes from UVA, Monticello and Fork Union Military Academy. Enjoy private parking, eye catching décor and a complimentary bottle of wine!

Designer cabin in the woods at Shennadoah NP

Come relax at our scandi inspired cabin in the woods. Five acres of pristine woods are the perfect backdrop for our renovated house, making it an ideal weekend retreat away from the busy city life. Discover the best spots in the area, including wineries and breweries, caverns and trails, antique shops and local makers, only a few miles from the house. Whether you are looking for a restful getaway, a source of inspiration, or a place to stay while you discover Virginia, this is the place for you.

Historic 1790 House Near Charlottesville

Originally a tavern built 1790 in the Williamsburg style, the Ordinary sits 6/10 mile off the main road--no other house in sight. 22 miles from Shenandoah National Park, convenient to local vineyards, the Ordinary is set on 650 acres in conservation easement; solar energy; generator in event of power outage; outdoor fire pit; 2 great fireplaces; wood provided by owner. The house is over 200 years old with narrow, steep steps and may not be suitable for children and people with mobility issues.

Sunset Retreat a cabin off the beaten path

Relaxation and quiet are two words that come to mind at Sunset Retreat. Close enough to stores for convenience but far enough away for solitude. Large yard, fire pit and concrete area if children want to create a masterpiece in chalk, there is also a tree swing next to woods. Close to many wineries, breweries and hiking. No WIFI or satellite tv, we have antenna only. You are welcome to bring your own hotspot . We have one smart tv. There is also a private in ground pool for summer time use.

Cox Mill House at Wolftrap Farm: Escape the City!

Get outdoors on our 600 acre horse & cattle farm, which is just across a country backroad from this house. Great for families visiting Monticello, UVA, attending weddings, or for groups coming to enjoy the local wineries and other Charlottesville area attractions. This makes our seventh vacation home at Wolf Trap Farm. Guests may visit the horses and cattle, hike the farm roads and woodland trails, swim in our creek, fish in our ponds, use our Game Barn, and book our hot tub patio.

Modern Getaway in Orange

Bring the whole family to this amazing home away from home in Orange, VA. Three spacious bedrooms and 2 1/2 luxurious bathrooms complete with an open concept kitchen, living room, office and extra family room. Just off Route 15 near the CVS with easy access to Woodberry Forest. Nearby points of interest include Monticello, Montpelier & many Civil War battlefields. Close to UVA sports/performances/restaurants/shopping. Or, simply relax on the back deck & take in the natural beauty.

Cozy Farmhouse Getaway

Life is good on the farm! The 3-bedroom house is a home-away-from-home where cows are your neighbors. You’ll be surrounded by rolling fields & open skies with beautiful sunrises and sunsets. Only 11 mi. to downtown Culpeper with MANY wineries, breweries and historical sites close by. Easy driving distance to the Shenandoah Mtns, Lake Anna, Fredericksburg, Charlottesville and DC. History buffs will enjoy knowing the farm was the site of the Civil War Battle of Morton's Ford.

Unit A-Mountain Retreat- SAUNA-Hiking-Wineries

Renovated duplex in Madison, VA. Enjoy a peaceful setting, amazing views and convenient to wineries, wedding venues & hiking. SAUNA! On-site walking trail. Near Early Mtn Vineyards, Prince Michelle Winery, Yoder's Market, Bald Top Brewing & Plow & Hearth. A 30 min drive to Charlottesville, Shenandoah Nat. Park, Culpeper & Orange. Shopping, restaurants, breweries, antiquing, site seeing and more. *RENT ENTIRE HOME* - Inquire for our unit A & B combined rate. Dogs allowed-$30 fee.

Hidden Haven

Hidden Haven is just that! A 600 square foot romantic, private, peaceful, little haven. Hidden in the woods just 6 miles outside of the Town of Orange. Open the garage door in the living area and step out on the 300 square foot screened in porch where you can relax at the firepit under the covered roof. On the porch at Hidden Haven, we like to say, "time wasted is time well spent". The romantic vibe and modern amenities make it a prefect place for a couple's getaway.