Pet-friendly vacation 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.

1 Bedroom Apartment With a Kitchenette on 28 Acres

Unique one bedroom apartment available for short or long term stays! Enjoy use of the kitchenette with microwave, air fryer, mini fridge, 2 burner hotplate, coffee maker, and dishes and cookware. Bedroom and living room combo space is sure to please with quaint built in bookcase and sloped ceilings - the perfect room to curl up and read or watch TV! Bathroom features a soaking tub and guest have access to another full bathroom with a standing shower. Check us out on IG #montlaurelweddings!

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.

Wine Country Cottage, Hot Tub, Game Room, Slps 12

Connect with family at this cozy cottage, nestled in the historic town of Gordonsville at the heart of Virginia's wine country. Gather all the family under one roof during your stay while taking excursions to award winning wineries, breweries, and attractions in and around Gordonsville or nearby in Charlottesville. When you're staying at the cottage, you'll find plenty to do with the game room, pool table, deck w hot tub, large fenced backyard, toys for kids, and more.

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! 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.

Luxury Couples Dome Hot Tub, Fire Pit & Stargazing

Slip away to a private couples-only dome on a peaceful 110-acre farm in Unionville, Virginia — just one hour from Washington, DC. Sleep beside a breathtaking panoramic window, soak in your private hot tub under the stars, and end the evening around the fire pit surrounded by nature. Designed for anniversaries, birthdays, proposals, baby moons, and quiet escapes, our luxury dome was created to help couples reconnect and unwind.

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!

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.