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, 292 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

Superhost

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, 134 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.

Guest favorite

A wide view of rolling green hills stretches into the distance, framed by a clear blue sky. The landscape showcases lush trees and open fields, providing a serene and natural backdrop. The image captures the tranquility of the countryside setting.

Farm stay in Barboursville

4.89 out of 5 average rating, 176 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 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, 261 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 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, 186 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 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, 432 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, 446 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

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, 464 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 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, 175 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.

Top guest favorite

The exterior of a two-story house is viewed, featuring a light-colored façade and green shutters. Two wooden chairs are positioned on the porch, accompanied by blooming planters. A star decoration is mounted above the door, adding a simple yet distinct touch.

Home in Culpeper

4.97 out of 5 average rating, 159 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 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, 141 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.

Superhost

A charming guest cottage is nestled among lush green landscaping. The structure features a metal roof and a porch with simple white railings. Tall trees provide shade, contributing to the serene atmosphere of the surrounding countryside.

Cottage in Madison

4.92 out of 5 average rating, 163 reviews

Charming Guest Cottage at Winery

Early Mountain Vineyards' charming Guest Cottage, nestled next to our front block of grapevines and below our historic hilltop barn, offers breath-taking views of the Blue Ridge Mountains and a serene place to watch the sunset while sipping wine. Only short distance to our Tasting Room - open 5 days a week, Thursday - Monday. We recommend a reservation in advance - this can be made via our website, Early Mountain Vineyards, or by calling our winery directly.