Family-friendly vacation rentals in Orange County

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Top-rated family-friendly rentals in Orange County

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Superhost

Villa in Orange

5 out of 5 average rating, 52 reviews

Luxurious Stay for 2 at Historic Estate

Nestled on 13.6 acres of exquisitely landscaped gardens & grounds, Boxwood Villa (circa 1891) is a hidden gem for a couple’s retreat. Named for its stunning boxwood bushes encircling the property, this historic home was thoughtfully renovated by Leslie Gregg, the founder of The Market at Grelen. Her keen eye for contemporary comfort & preservation of historic design breathes new life into this historic manor. *Please note we only accept bookings for couples 30 days out from the requested dates.*

Superhost

Home in Orange

4.83 out of 5 average rating, 273 reviews

ATLAST - THE FARMHOUSE

Don't let the exterior fool you, this brick home is decorated in Farmhouse Style, 1 mile from Historic Montpelier, 3 miles from Grelan Nursery, Orange, Willow Grove Inn and Woodberry Forest School. Across from a 30 acre farm. Gaze out the window at the horses and cattle, take a hike on a nearby trail or visit the many wineries in the area. Close to Charlottesville( 30 miles) Culpeper (20 miles) 1 and a half hours to DC. 20 minutes to HITS Horse show, Culpeper. Woodbrook Winery around the corner

Superhost

Farm stay in Rapidan

4.86 out of 5 average rating, 127 reviews

Iconic Virginia Farmhouse with Furnished Silo

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.

Superhost

Chalet in Mineral

4.71 out of 5 average rating, 277 reviews

Private Lake Anna Waterfront Chalet w/dock/beach!

Your cozy lakefront chalet is steps away from deep water and fun adventure. With sandy beach, fire pit, fabulous dock area, hammock, canoe, kayaks, and SUP, you will enjoy your lake vacation. Room to bring a boat and/or jet skis w/ community boat launch. High speed Internet, swingset, on a large private lot with woods between neighbors. Large deck overlooking lake with gas grill. The property has 250' of prime main lake frontage with fishing, dining, and sunbathing on dock. Pet friendly!

Family-friendly vacation rentals in Orange County

Top-rated family-friendly rentals in Orange County

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Popular amenities for Orange County family-friendly rentals

Family-friendly home rentals with a hot tub

Home in Gordonsville

Cottage in Gordonsville

Home in Gordonsville

Home in Gordonsville

Cottage in Gordonsville

Barn in Gordonsville

Family- and pet-friendly home rentals

Rental unit in Orange

Home in Orange

Cottage in Gordonsville

Guesthouse in Madison

Cottage in Gordonsville

Home in Orange

Cottage in Gordonsville

Farm stay in Rapidan

Family-friendly home rentals with Wifi

Home in Orange

Home in Gordonsville

Rental unit in Orange

Home in Barboursville

Home in Orange

Serviced apartment in Somerset

Cottage in Gordonsville

Farm stay in Rapidan

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