Pet-friendly vacation 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

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.

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!

Clifton House | An Equestrian Getaway

Enjoy a stay at the Clifton House, a beautifully restored historic estate in central Virginia. Built in 1780, this elegant home retains original architectural details while offering modern comforts throughout. The property is situated on 240 private acres, offering views of the Blue Ridge foothills and picturesque horse pastures. Guests can enjoy a luxurious equestrian retreat with access to top-tier, on-site equine amenities and well-trained horses available for guided rides across the estate.

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!

Lakefront Cabin • Dock • Sunset Views

Gather your people and settle into this spacious Lake Anna waterfront cabin, thoughtfully designed for families, multi-generational groups, and friends traveling together. Enjoy open lake views, a screened-in porch, a private dock, kayaks, paddleboards, and a well-equipped kitchen perfect for cooking and gathering around a large dining table. With plenty of room to spread out and welcoming hosts who are always available, this is a relaxed, comfortable lake home made for connection.

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.

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.

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.