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Vacation rentals in Orange County

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Top-rated vacation rentals in Orange County

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Home in Orange

4.83 out of 5 average rating, 273 reviews

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

Guesthouse in Orange

5 out of 5 average rating, 229 reviews

Taj Garage Guesthouse

Newly constructed (2021) above garage guesthouse with private, self check-in entrance, off-street parking, located among historic homes just 4 blocks to restaurants, shops, park and art galleries in downtown Orange. Guesthouse includes a fully equipped kitchen, queen bed, full bath, seating area, TV, wifi and balcony. Handcrafted heart pine furniture. Level 2 EV Charger. Kitchen includes refrig, stove, microwave, toaster and Keurig. Close to superb wineries, breweries and historic sites.

Serviced apartment in Somerset

4.99 out of 5 average rating, 170 reviews

Newly Renovated•Private Farm Apartment near Cville

Come experience a relaxing getaway on our family’s dairy farm! Set in beautiful Orange County, We are close enough to Charlottesville (25 min) to fulfill all your shopping and eating needs, but have the privacy, calm and tranquility of the country, with beautiful majestic mountain views! This is a wonderful location for exploring all of wine country, unwinding from the hustle of busy life, and then taking in the sunset in this quiet country setting with rolling hills as your backdrop!

Bungalow in Orange

4.99 out of 5 average rating, 400 reviews

Farm Cottage just outside town of Orange.

Charming 1920's cottage on a large farm just outside the town of Orange. Completely renovated and updated. Convenient to vineyards, battlefields, wedding venues and popular tourist destinations. Bucolic setting, very private. Spaces to enjoy the out of doors. Less than 2 miles to in-town wedding venues and Rounton Farm. Less than 4 miles to Inn at Willow Grove. 5 miles to Montpelier. Less than 7 miles to Grelen. 10 miles to Gordonsville. 12 miles to Barboursville. 19 miles to Mineral.

Cottage in Orange

4.95 out of 5 average rating, 411 reviews

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!

Rental unit in Gordonsville

4.98 out of 5 average rating, 423 reviews

A private apartment with Self Check-in.

This newly renovated one bedroom apartment is in the heart of historic downtown Gordonsville. No box stores here, just quaint shops and restaurants. The apartment is right on Main Street nestled in the middle of boutique shops and brick sidewalks with Monticello, Montpelier, the University of Virginia, Shenandoah National Park, local vineyards and many historic sites near by. This is a private second story apartment above a local business with a separate entrance and key-less entry.

Cottage in Gordonsville

5 out of 5 average rating, 154 reviews

Merry View Cottage

Our newly renovated farm cottage sits at the edge of a grove of giant hardwoods. Enjoy year round mountain views, including Merry Mountain. Ease into the morning while watching wildlife from a front porch rocker. Visit local wineries, breweries, restaurants, museums, shops, hiking trails or wedding venues. Unwind in the hammock or practice yoga on the back deck. Prepare dinner in our full size kitchen. Then, star gaze around the fire-pit after dark. This peaceful oasis awaits you.

Farm stay in Brightwood

4.96 out of 5 average rating, 122 reviews

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.

Home in Orange

4.98 out of 5 average rating, 101 reviews

Hidden Haven

Hidden Haven is just that! A 600 square foot romantic, private, peaceful, little haven. Hidden in the woods just 6 miles outside of the Town of Orange. Open the garage door in the living area and step out on the 300 square foot screened in porch where you can relax at the firepit under the covered roof. On the porch at Hidden Haven, we like to say, "time wasted is time well spent". The romantic vibe and modern amenities make it a prefect place for a couple's getaway.

Cottage in Spotsylvania Courthouse

4.87 out of 5 average rating, 145 reviews

Bond House: Historic Retreat at Walnut Grove

Escape from the city to a historic 1740s cottage with a distant view of the Blue Ridge Mountains and peaceful surroundings with the opportunity to experience the slower pace of country living. Spend the day at Lake Anna to swim/ kayak/ boat or visit the state park, just 5 minutes away. Enjoy local wineries, and explore historic Civil War battlefields. After a fun filled day, return to your private oasis with a fully equipped kitchen.

Cottage in Ruckersville

4.9 out of 5 average rating, 298 reviews

Lake Haven Cottage

Make yourself at home at our peaceful 1-bedroom cottage that has everything you need for your trip to the Blue Ridge Mountains. The cottage comes with heating, AC, Washer+Dryer and DIRECTV. During your stay, you can also enjoy using a convenient private bathroom, kitchen, and living room. Our Airbnb is within driving distance to UVA, the Skyline Drive & Shenandoah National Park, local wineries, craft breweries and much more!

Rental unit in Orange

4.94 out of 5 average rating, 392 reviews

Cardinal Cove: Waterfront Kayaks Firepit Boatslip

Waterfront Lake Anna; vineyards/state park/walking trails/patio seating gas grill; granite counter tops/gas stove/large refrig. Baths newly tiled. Walk-in shower in master bedroom. Three queen size beds, 2 deluxe air mattresses. 65" 4k SU Samsung tv (240 channels/11 movie channels; plus movies on-site). Quiet hours: 11pm-8am. Kayaks for 6 available upon request must return to storage rack face down or $25 cleaning fee.

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Popular amenities for Orange County vacation rentals

Free parking on premises

Air conditioning

Other great vacation rentals in Orange County

Home in Orange

5 out of 5 average rating, 47 reviews

Tatums Farmside Escape a country jewel Sleeps 10

Villa in Gordonsville

4.98 out of 5 average rating, 63 reviews

Restored Historic Stone Greenhouse

Home in Aroda

4.9 out of 5 average rating, 92 reviews

The Nest on Hawks Ridge

Home in Aroda

4.97 out of 5 average rating, 78 reviews

Sunset Retreat a cabin off the beaten path

Home in Madison

5 out of 5 average rating, 50 reviews

Winter is beautiful.

Home in Unionville

5 out of 5 average rating, 18 reviews

The Farmhouse At Oak Creek Farm

Home in Orange

5 out of 5 average rating, 62 reviews

Lake Anna Lakefront Retreat

Rental unit in Orange

5 out of 5 average rating, 30 reviews

Fornow Farm Country Apartment

Destinations to explore