Pet-friendly holiday rentals in Orange County

4.84 out of 5 average rating, 298 reviews

Home in Orange

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

4.94 out of 5 average rating, 118 reviews

Home in Madison

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.

4.86 out of 5 average rating, 137 reviews

Farm stay in Rapidan

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.

4.96 out of 5 average rating, 455 reviews

Cottage in Orange

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!

4.93 out of 5 average rating, 143 reviews

Farm stay in Brightwood

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.

4.95 out of 5 average rating, 429 reviews

Home in Madison

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.

4.9 out of 5 average rating, 250 reviews

Cabin in Unionville

Private Couples getaway with HOT TUB.

Welcome to the exquisite location, conveniently situated only 15 minutes away from Lake Anna. Our family has invested significant effort into creating this splendid, contemporary A-frame cabin, nestled on our 110 acre family farm. Strategically positioned to offer a breathtaking view of the creek that traverses our property, this private retreat is located just one hour from Washington, D.C. Immerse yourself in the tranquil ambiance and soothing sounds of nature.

Tiny home in Gordonsville

4.99 out of 5 average rating, 129 reviews

The Little House: Screened Porch + Pasture Views

Are you looking for a relaxing getaway weekend in Virginia's countryside? Welcome to The Little House! This tiny house (~300 sq ft) is located on five acres overlooking a private pasture in the scenic countryside of Gordonsville. Located just a 3-minute drive from downtown Gordonsville, the home is the perfect launching point to some of Central Virginia's best wineries, historic sites, and area attractions.

4.88 out of 5 average rating, 410 reviews

Cabin in Madison

The Cabin at the Lake

Lake view cabin! 2 bedrooms one bathroom. Close to breweries, wineries, grocery store, and 20 minutes from Shenandoah National Park. You will have everything you need at our home provided for you. We have a canoe and row boat for you to venture out on the water and fishing poles, just bring your tackle, bait and bathing suit! We have high speed internet (100+mbps) at the cabin and a smart Tv! No parties!

4.85 out of 5 average rating, 161 reviews

Cottage in Gordonsville

Quaint Cottage - Wolftrap Farm (Horse neighbors)

From the large covered patio of this little cottage, you can watch the horses, see our largest pond, eat your meals if you choose, and marvel at the beauty of nature. You can also book our hot tub patio, swim in our creek, fish in our ponds, hike our many miles of farm roads and woodland trails, use our Game Barn, and sip wine as you watch the sun set behind the mountains.

4.95 out of 5 average rating, 450 reviews

Cottage in Madison

THE PERFECT HIKING & WINERY COUNTRY RETREAT

Welcome! Our charming 2 bedroom guesthouse is located in the middle of our 23 acre farm. Currently the property is being used for livestock - cattle (and one donkey named Jasper). Please note: The pool will be open the first week in May thru Labor Day Weekend (sometimes longer if weather permits).