Family-friendly holiday rentals in Orange County

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

The Studio at Dark Run Retreat

Quiet studio on a secluded 5 acres only 3 miles from town. Kick back and relax by the pool in the warmer months, or in the hot tub in the cooler months. Small trails lead to the creek running along the property, maybe you'll even catch a glimpse of the deer or turkey that wander thru...we've even seen a lil bear once! There is an apartment above the studio, so we ask that you be mindful of those guests if occupied. *The studio got a make-over! As of 10/6/20, we will no longer be hosting pets*

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".

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.

A private apartment with Self Check-in.

This newly renovated one bedroom apartment is in the heart of the historic district of Gordonsville. No box stores here, just quaint shops and restaurants. The apartment is right on Main Street nestled in the middle of boutique shops and brick sidewalks with Monticello, Montpelier, the University of Virginia, Shenandoah National Park, local vineyards and many historic sites near by. This is a private second story apartment above a local business with a separate entrance and key-less entry.

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!

Merry View Cottage

Our newly renovated farm cottage sits at the edge of a grove of giant hardwoods. Enjoy year round mountain views, including Merry Mountain. Ease into the morning while watching wildlife from a front porch rocker. Visit local wineries, breweries, restaurants, museums, shops, hiking trails or wedding venues. Unwind in the hammock or practice yoga on the back deck. Prepare dinner in our full size kitchen. Then, star gaze around the fire-pit after dark. This peaceful oasis awaits you.

Gordonsville Guest Cottage - private studio

Welcome to the Gordonsville Guest Cottage, located in historic Gordonsville, VA. This is the perfect escape into small-town living, with all the necessities nearby. Close to numerous vineyards and historic sites. Relax and unwind in this 300 sq ft private guest house which includes a queen bed, living area, bathroom, and kitchenette. This cottage is in our backyard and next to train tracks. You will need to walk 150 ft from dedicated parking. No pets.

Moonfire Farm cozy Shenandoah Region Getaway

Experience charm and nature at Moonfire Farm! Our finished basement on a 5-acre hobby farm offers delightful animal encounters with chickens, ducks, alpacas, and hilarious goats. Our active family of three, including our 7-year-old daughter Piper, welcomes you. High-speed Internet and nearby wineries, breweries, hiking trails, and pick-your-own fruit locations await you. Explore our guidebook for recommendations. Book now for a memorable farm getaway!

Lake Haven Cottage

Make yourself at home at our peaceful 1-bedroom cottage that has everything you need for your trip to the Blue Ridge Mountains. The cottage comes with heating, AC, Washer+Dryer and DIRECTV. During your stay, you can also enjoy using a convenient private bathroom, kitchen, and living room. Our Airbnb is within driving distance to UVA, the Skyline Drive & Shenandoah National Park, local wineries, craft breweries and much more!

The Nest on Hawks Ridge

The Nest on Hawks Ridge is in the heart of all you want to do in Central Virginia! Newlyweds to families, everyone will love it here! The peace and quiet of the country, or the excitement of exploring new and different places all await you! Check out our Guidebook for local attractions, restaurants, nightlife and sightseeing. Enjoy the serenity of the country! Follow us: @nestonhawksridge