Vacation rentals in Orange County

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Top-rated vacation rentals in Orange County

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Guest favorite

Home in Orange

4.84 out of 5 average rating, 291 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

Guest favorite

A well-organized laundry area features two white washing machines and a matching dryer. Light wood cabinets provide storage above a smooth granite countertop, which includes a small sink. The space is illuminated by soft, natural light reflecting off the neutral wall color.

Farm stay in Barboursville

4.89 out of 5 average rating, 174 reviews

Suite with Views of Vineyards and Mountains.

Quiet- Beautiful- Spacious 2nd story with views of the Countryside, Southwest Mountains and Blue Ridge. Guests have walked to Barboursville and Barn 678 Vineyards. 25 minutes from Charlottesville. 11 wineries, 2 breweries & 1 Cidery within 10 miles. 40 minutes to the Shenandoah National Park. We are cooks & have furnished kitchen for those that like to cook. We sell local eggs, herbs, preserves, produce and honey harvested on the property. Access to the property is from an exterior stairway.

Top guest favorite

A gravel driveway leads through a landscaped area, surrounded by lush greenery and trees. A separate building is visible among the vegetation, contributing to the serene outdoor space. The scene is bright with natural light, creating an inviting atmosphere.

Guesthouse in Orange

5 out of 5 average rating, 258 reviews

Taj Garage Guesthouse

Above garage guesthouse with private, self check-in entrance, off-street parking, among historic homes, 4 blocks to restaurants, shops, park, etc. in downtown Orange. Includes a fully equipped kitchen, queen bed, full bath, seating area, TV, wifi and balcony. Custom heart pine furniture, EV charger, refrig, stove, microwave, toaster and Keurig. Close to superb wineries, breweries and historic sites. Four blocks from the railroad so you will occasionally hear "that lonesome whistle blow".

Top guest favorite

Apartment in Somerset

4.98 out of 5 average rating, 184 reviews

Cozy Farm Apt near Cville•wineries, mt. views

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!

Top guest favorite

A vibrant flower bed is surrounded by a black wooden fence, featuring a variety of flowers including zinnias, daylilies, and other seasonal blooms. The lush green grass provides a well-maintained backdrop, contributing to the peaceful outdoor setting.

Bungalow in Orange

4.99 out of 5 average rating, 429 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.

Top guest favorite

A wooden deck features a round table and two matching chairs, both in a vibrant turquoise color. The railing offers a clear view of the surrounding grassy area and trees, creating a serene outdoor space.

Cottage in Orange

4.96 out of 5 average rating, 442 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!

Top guest favorite

A bright open kitchen and dining area is presented, featuring a white table set with dinnerware. A spacious white sofa is positioned nearby. Large sliding glass doors provide access to the outdoor deck, enhancing the indoor-outdoor connection. Neutral tones dominate the decor for a modern feel.

Home in Orange

4.96 out of 5 average rating, 24 reviews

Modern Getaway in Orange

Bring the whole family to this amazing home away from home in Orange, VA. Three spacious bedrooms and 2 1/2 luxurious bathrooms complete with an open concept kitchen, living room, office and extra family room. Just off Route 15 near the CVS with easy access to Woodberry Forest. Nearby points of interest include Monticello, Montpelier & many Civil War battlefields. Close to UVA sports/performances/restaurants/shopping. Or, simply relax on the back deck & take in the natural beauty.

Top guest favorite

A view of historic Main Street is presented, with brick storefronts lining both sides. An American flag stands prominently in the foreground. Decorative plants enhance the streetscape, and the sidewalk is bordered by a neatly manicured flower bed, contributing to the inviting atmosphere.

Apartment in Gordonsville

4.97 out of 5 average rating, 462 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.

Top guest favorite

A front porch is showcased, featuring two white rockers positioned on a wooden deck. The scene is enhanced by a misty landscape in the background as the sun rises over rolling hills, casting a soft light on the surroundings.

Cottage in Gordonsville

5 out of 5 average rating, 174 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.

Guest favorite

A wooden sign hanging from a black post indicates the entrance to Tri Creek Farm. The sign displays the name prominently in a simple font, and the surrounding area features a gravel road with grassy fields on either side, under an overcast sky.

Farm stay in Brightwood

4.94 out of 5 average rating, 139 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.

Top guest favorite

A gravel driveway lined with green grass leads through expansive fields. A wooden fence runs parallel to the driveway, framing the lush landscape. The horizon features trees and a glimpse of the house in the distance, under a sky transitioning from day to dusk.

Home in Culpeper

4.97 out of 5 average rating, 158 reviews

Cozy Farmhouse Getaway

Life is good on the farm! The 3-bedroom house is a home-away-from-home where cows are your neighbors. You’ll be surrounded by rolling fields & open skies with beautiful sunrises and sunsets. Only 11 mi. to downtown Culpeper with MANY wineries, breweries and historical sites close by. Easy driving distance to the Shenandoah Mtns, Lake Anna, Fredericksburg, Charlottesville and DC. History buffs will enjoy knowing the farm was the site of the Civil War Battle of Morton's Ford.

Top guest favorite

A screened-in porch is highlighted with a comfortable seating area featuring dark sofas adorned with neutral-toned blankets. Two ceiling fans provide air circulation. The surrounding wooded landscape is visible through large glass doors, enhancing the connection to nature.

Home in Orange

4.97 out of 5 average rating, 138 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.