Pet-friendly 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!

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.

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!

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

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.

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.

Barn Apartment at Wolftrap Farm - Escape the City!

Barn Apartment at Wolftrap Farm - 2017 Conversion of horse barn wing to gorgeous apartment. Huge horse & cattle farm, with easy access to Monticello, Montpelier, 6 wineries. 5 miles to Gordonsville or Orange; 25 miles to Charlottesville. Gorgeous countryside. Bring the kids and/or dogs. They will be thrilled, as will the adults. Book our hot tub patio, swim in our creek, fish in one of the ponds, hike our farm roads and woodland trails, play in our Game Barn.

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.

Country Cottage with Modern Amenities

Looking for a relaxing weekend getaway in Virginia's countryside? Welcome to the Shade Tree Cottage! This home dates back to the Civil War and is full of cottage vibes. Located just a 3-minute drive from downtown Gordonsville, the home is the perfect combination of rural retreat and launch pad to some of Central Virginia's best wineries, historic sites, and attractions.

Madison Farmette Guest House

Early Mountain Vineyards is a little over a mile from our place. We are minutes from the SNP trails and Bald Top Brewery. Enjoy this private getaway that is convenient to hiking, wine tours, art workshop weekends, biking, hot air ballooning, antiquing, all in a genuinely welcoming community that offers a great lifestyle.

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).