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!

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.

Lake Anna Waterfront w/ Hot Tub & Private Dock

Welcome to Homeport Harbor — your relaxing Lake Anna escape. This spacious waterfront retreat on the public side of Lake Anna is perfect for couples, families, and group getaways. Set on a private one-acre lot, the updated home features stylish furnishings, an open kitchen, and comfortable mattresses throughout. Spend your days kayaking, swimming, fishing, or relaxing from the private dock, then unwind in the hot tub, screened porch, or around the fire pit under the stars. Lake life awaits.

The Lake Lodge: Private Slip, Lake Access, Hot Tub

Welcome to the Lake Lodge! You're invited to this peaceful retreat among a canopy of trees. The home is a 3 minute walk to the lake (public side), with a private slip, HOA sitting area, & boat ramp. When you aren't admiring the lake views from the HOA dock, savor the forested yard with built in firepit, cozy hot tub, & gigabit WIFI. After a long day of fishing, boating, or hiking, the home welcomes you with a stocked kitchen, outdoor grill, TVs in each room & a soaking tub. Relaxation awaits!

Elegant Historic Home Walkable to Downtown Orange

This beautifully restored 1920s Victorian was designed for slow mornings, wine-country weekends, and meaningful time together. Tucked along a quiet tree-lined street just steps from downtown Orange, this elegant retreat blends historic charm with elevated comfort. From the spacious front porch to the marble kitchen, every detail feels warm, beautiful, and memorable. Whether you’re here for a wedding weekend, vineyard escape, or peaceful getaway, we invite you to slow down and stay awhile.

The Farmhouse At Oak Creek Farm

The Farmhouse at Oak Creek Farm is a newly renovated turn of the century farmhouse that is nestled on 85 serene and peaceful acres. Our home is ideal for families and large groups coming to Central Virginia for weddings at Oak Creek Farm or to get away from city life for a bit. Forget your worries in this spacious and serene space. Start your day enjoying the farm life with a breathtaking sunrise while the cows wake up and start grazing across the fields located directly behind the house.

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.

R&R at LAKE ANNA Waterfront 6 BR/6 Bath Dogs yes

R&R at Lake Anna...6 Bedrooms / 6 Full Bathrooms (17 total beds) It's time for some R&R! R&R at Lake Anna welcomes you to a comfortable lakefront home boasting 470 feet of water frontage on the public side of Lake Anna at the northwestern part of the lake. Nestled in over 3 acres of mature forest, R&R offers a modern cabin vibe. You will enjoy panoramic and stunning sunrise and sunset views of Lake Anna on one side and the privacy of being at home among the trees on the other.

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

Cozy Farmhouse Getaway

Life is good on the farm! Our charming three-bedroom guest house offers a true home-away-from-home experience, where rolling fields, open skies, and friendly cows are your closest neighbors. Enjoy breathtaking sunrises and sunsets in a peaceful countryside setting, just 11 miles from downtown Culpeper. You’ll be close to numerous wineries, breweries, and historic sites, with easy day trips to the Shenandoah Mountains, Lake Anna, Fredericksburg, Charlottesville, and Washington, DC.

White Oak Creek’s Hidden Haven

Escape the busyness of life at this peaceful and centrally-located getaway. Explore historic sites in the Central Virginia area, visit wineries and breweries, stroll the main streets of quaint small towns, or hike the Blue Ridge mountains. Hidden Haven is conveniently located near multiple wedding venues, UVA, and Woodberry Forest School. Enjoy the creek, walking trails, fire pit, swings, and stunning sunsets at Hidden Haven, along with the seasonal beauty of adjacent farms.

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.