Vacation rentals in Orange County

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Top-rated vacation rentals in Orange County

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Guest favorite

The entryway is adorned with a festive wreath hanging on the door. A decorated sign reading 'Christmas' is positioned next to the door, accompanied by a potted plant and two decorative planters featuring seasonal foliage.

Home in Orange

4.84 out of 5 average rating, 302 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

The farm-style house features a modern design with light-coloured siding and large windows, allowing natural light to permeate the space. A cylindrical silo adjoins the structure, creating unique architectural interest. The grassy expanse surrounding the home offers a serene, open landscape.

Farm stay in Rapidan

4.86 out of 5 average rating, 138 reviews

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.

Top guest favorite

A newly constructed guesthouse features a charming exterior with a sloped red roof and white trim. A covered balcony with a red umbrella overlooks landscaped gardens. Stone pathways and greenery surround the home, enhancing the inviting outdoor space.

Guesthouse in Orange

5 out of 5 average rating, 276 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

The exterior of La Petite Maison showcases a charming guest house with a large screened porch, surrounded by vibrant flower beds. A turquoise umbrella shades a lounge chair next to the seasonal in-ground pool, providing a relaxing outdoor space.

Guesthouse in Gordonsville

4.91 out of 5 average rating, 185 reviews

La Petite Maison at Hedgeapple Hollow

La Petite Maison (our guest house) is the perfect place to simply get away from the hustle and bustle and relax! Sit in the private screen porch and watch the sun melt into the mountains. Deer, hummingbirds, bluebirds, and the occasional turkey like to hang out on the 8 acres of the property, perfect for any wildlife lover. Enjoy the fenced in common area featuring a seasonal in-ground pool. Conveniently situated near award-winning wineries, Montpelier, and historic downtown Gordonsville.

Top guest favorite

The entrance features double wooden doors that open to a welcoming interior. A 'hello' mat is placed on the threshold, and two stylish chairs are positioned on the balcony above, inviting guests to enjoy the view. Lush plants accentuate both sides of the entrance.

Apartment in Somerset

4.98 out of 5 average rating, 189 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

The entrance features a solid wooden door with glass paneling, displaying the name 'Main Street Airbnb.' A decorative yellow wreath adorns the door, and vibrant flowers are planted near the base, enhancing the welcoming appearance of the entryway.

Apartment in Gordonsville

4.97 out of 5 average rating, 482 reviews

A private apartment with Self Check-in.

This newly renovated one bedroom apartment is in the heart of the historic district of 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 charming green cottage is presented, featuring a small front porch with two chairs and potted flowers. Large windows allow natural light to fill the space, while the surrounding landscape includes grassy areas and trees, providing a peaceful rural setting.

Bungalow in Orange

4.99 out of 5 average rating, 446 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 living area features a comfortable gray sofa and armchair, set on a light area rug. A wooden coffee table is centrally located, while a TV sits on a decorative stand. Natural light enters through a window, complemented by soft lighting from a chandelier above.

Cottage in Orange

4.96 out of 5 average rating, 460 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 view from an open doorway reveals a covered porch with white rocking chairs. A welcome mat lies on the wooden floor, leading to a scenic landscape of rolling hills adorned with autumn foliage. A glimpse of black chairs is visible in the distance.

Cottage in Gordonsville

5 out of 5 average rating, 182 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 modern cabin-style home is nestled among tall trees, showcasing a sleek black exterior. A spacious screened-in porch is visible, supported by a deck with steps leading down to a gravel path. Large windows enhance the connection with the natural surroundings.

Home in Orange

4.97 out of 5 average rating, 151 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.

Top guest favorite

A charming guest cottage is set amidst greenery, featuring a welcoming front porch with white railings. Stone steps lead to the entrance. An inviting garden surrounds the cottage, complemented by decorative landscaping and trees in the background, creating a serene outdoor environment.

Guesthouse in Gordonsville

4.96 out of 5 average rating, 103 reviews

Gordonsville Guest Cottage - private studio

Welcome to the Gordonsville Guest Cottage, located in historic Gordonsville, VA. This is the perfect escape into small-town living, with all the necessities nearby. Close to numerous vineyards and historic sites. Relax and unwind in this 300 sq ft private guest house which includes a queen bed, living area, bathroom, and kitchenette. This cottage is in our backyard and next to train tracks. You will need to walk 150 ft from dedicated parking. No pets.

Guest favorite

A charming historic cottage is featured, showcasing a white exterior with a red metal roof. The front porch is framed by a small staircase and surrounded by well-maintained greenery. Tall trees provide shade on the side, set against a backdrop of an expansive blue sky.

Cottage in Spotsylvania Courthouse

4.89 out of 5 average rating, 174 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.