Pet-friendly holiday rentals in Orange County

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.

Quaint & Cozy LakeView Cottage - Lake of the Woods

Welcome to Brent and Carla's Lake View Cottage! Our beautifully renovated, fully furnished, unique and luxurious home is stocked with everything you need to enjoy your stay in beautiful Lake of the Woods. Our cozy cottage is a perfect get-away for your next vacation, visit with family, work trip, staycation or weekend getaway. You will instantly be set at ease as you enter our home featuring wonderful décor, detailed craftsmanship and lots of amenities to make your stay relaxing and memorable.

The Cottage At Liberty Mill. Pets allowed $25

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. Great for kids. Beautiful.

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.

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!

Relaxing 2BR CABIN, 12 acres, dog friendly, hiking

Bring the whole fur family & enjoy precious time away from the hustle & bustle of everyday life. This updated cabin sits on 12.5 acres of mainly wooded land in the heart of the blue ridge- Madison County. Within 30 minutes of wineries, breweries, hiking, & Charlottesville! Boasting a primary loft bedroom w/ a queen bed and a bonus room w/ a full bed, this home away from home can comfortably sleep 4-5! Front porch swing & fenced yard for the pups to play. Guests can completely relax!

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.

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.

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.

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!

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.

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).