Holiday rentals in Woodberry Forest

Iconic Farmhouse w/ Furnished Silo & Highland Cows

This beautiful house is the culmination of eight friends’ vision for an ecological and architectural experience. Set on a picturesque 33-acre grassfed cattle farm, this 4 bedroom, 3 loft, 2.5 bath dwelling is ideal for family get-togethers and intimate reunions with old friends. Many Blue Ridge Mountain sunsets have been celebrated from the open air balcony. Due to the number of staircases and separated rooms, the property is not ideal for folks with toddlers or those with mobility limitations.

Tatums Farmside Escape a country jewel Sleeps 10

Relax & enjoy gorgeous views of farmland, mountains and grazing cattle. Perfect for multifamily stays, wedding parties, vacations.. Short drive to Orange & Culpeper. Near wineries such as Early Mtn , Prince Michelle, Barboursville etc. Historic areas near such as Montpelier. Visit local breweries Bald Top and Iron Pipe. Madison County borders the Shenandoah Nat Park where you can hike, fish & site see. Your stay includes coffee, toiletries, firewood, linens and towels. FIREFLY FAST INTERNET!

Taj Garage Guesthouse

Above garage guesthouse with private, self check-in entrance, off-street parking, among historic homes, 4 blocks to restaurants, shops, park, etc. in downtown Orange. Includes a fully equipped kitchen, queen bed, full bath, seating area, TV, wifi and balcony. Custom heart pine furniture, EV charger, refrig, stove, microwave, toaster and Keurig. Close to superb wineries, breweries and historic sites. Four blocks from the railroad so you will occasionally hear "that lonesome whistle blow".

Cozy Farm Apt near Cville•hot tub, sauna, mt views

Come experience a relaxing getaway on our family’s dairy farm in Somerset. In beautiful Orange County, We are close enough to Charlottesville (25 min) for all your shopping and eating needs, but has the privacy, calm and tranquility of the country, with beautiful majestic mountain views! This is a wonderful location for exploring all of wine country, unwinding from the hustle of busy life, and then taking in the sunset in this quiet country setting with rolling hills as your backdrop!

Elegant Historic Home Walkable to Downtown Orange

This beautifully restored 1920s Victorian in Orange, VA, was designed for slow mornings, wine-country weekends, and meaningful time together. Perfect for 4 guests, this 2-bed, 2-bath home blends historic charm with modern luxury. Featuring a chef's kitchen, a dedicated workspace, and a cozy fireplace, this home seamlessly blends historic charm with elevated comfort. Whether you’re here for a wedding weekend, vineyard escape, or peaceful getaway, we invite you to slow down and stay awhile.

Farm Cottage just outside town of Orange.

Charming 1920's cottage on a large farm just outside the town of Orange. Completely renovated and updated. Convenient to vineyards, battlefields, wedding venues and popular tourist destinations. Bucolic setting, very private. Spaces to enjoy the out of doors. Less than 2 miles to in-town wedding venues and Rounton Farm. Less than 4 miles to Inn at Willow Grove. 5 miles to Montpelier. Less than 7 miles to Grelen. 10 miles to Gordonsville. 12 miles to Barboursville. 19 miles to Mineral.

Private Fenced Yard for Dogs/Horses - 2BR Cottage

2BR Hen and Hound Cottage is located just outside Orange, VA and has a private fenced yard for pets and walk-in access to adjacent James Madison's Montpelier and its many walking trails. In addition, we are minutes away from all of the popular wedding venues in Orange and a short drive to Shenandoah National Park. Our house on Whistle Stop Farm (so named for the train that passes by) is next to the cottage if you need us. Otherwise, the place is yours. Come enjoy some time in country!

One Of A Kind Home in VA Wine Country on 50 acres

Welcome to Lumusa Lodge. Leave your cares behind as you turn onto the windy road that leads you to this beautiful 50-acre retreat. We are proud to share our home and hope your time here is rejuvenating. Designed/built by a Hollywood actor and situated in wine country, this home is an hour from Dulles, 45 minutes from Charlottesville & 15 minutes from Culpeper. We have an adjacent farmhouse if you need additional space. Great venue for weddings, bachelorettes, and other special events.

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.

The Cottage At Liberty Mill Upgraded WI FI Pet $50

Brand new charming cabin with views of the Blue Ridge Mountains. Two bedrooms, Loft with 2 twin beds, two large bathrooms and a spacious common area. Exposed chestnut beams, working gas fireplace make this cabin a perfect getaway. All the amenities you could want. Located minutes from James Madisons' Montpelier, 5 minutes from Historic Orange, 30 minutes to Charlottesville, 20 minutes to Culpeper and less than 2 hours to Washington, DC. A loft area with 2 twin beds. Upgraded WIFI

Robinson River Cabin - Tri Creek Farm

If you spend most of your career glued to a computer and other screens, this place is for you. TriCreek Farm is a place for you to disconnect, reboot, and fuel your soul. This riverfront cabin is situated on ~100 acres, over 1/2 mile of Robinson River frontage, with breathtaking views. There are creeks, fishing, and hiking trails to explore and enjoy. The cabin is located in Brightwood, Virginia, a small town located in Madison County between Culpeper and Charlottesville Virginia.

Cozy Country Cottage

"Cozy Country Cottage" is a rare find. It's located in a quiet neighborhood surrounded by beautiful farmland. It has a self check-in entrance, parking next to house and an amazing view of sheep grazing in pasture across the road. It's close to wineries, breweries, historic sites such as Mount Pelier, Monticello which is 23 miles, Woodberry Forest School which is 10 mins. away, shopping, hiking and more. Come and enjoy the quite, peaceful country !