Vacation rentals in Orange

5 out of 5 average rating, 256 reviews

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

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".

4.91 out of 5 average rating, 180 reviews

A spacious loft area features high, sloped wooden ceilings with exposed beams, allowing natural light to fill the room. Large windows offer scenic views, while a combination of seating options and tables creates an inviting space for relaxation or socializing.

Cottage in Orange

Willie's Place Country Cottage Pets Allowed

Step out your front door and pet horses located next door. Willie's place is newly renovated and has all the amenities you need. Located close to wineries, shopping, wedding venues, Historic Montpelier, Corn Maze, Town of Orange, Woodberry Forest School, 10 minutes to Gordonsville, 30 minutes to Charlottesville. Kayak the Rapidan, take a horseback ride at Oakland Heights or see a play at Barboursville. Exposed beams throughout, a beautiful Loft and back porch for sitting. You won't go wrong.

Guesthouse in Gordonsville

A serene sunset is depicted, with the sun slowly descending behind a mountain range. Silhouetted trees create a natural border, while a soft glow of orange and pink hues fills the sky, illustrating a calm and tranquil evening atmosphere.

4.91 out of 5 average rating, 182 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.

4.98 out of 5 average rating, 184 reviews

Apartment in Somerset

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!

4.99 out of 5 average rating, 428 reviews

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

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.

4.96 out of 5 average rating, 441 reviews

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

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!

Apartment in Gordonsville

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.

4.97 out of 5 average rating, 460 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.

5 out of 5 average rating, 172 reviews

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

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.

4.88 out of 5 average rating, 126 reviews

Dome in Unionville

luxury couples retreat with HOT TUB!

This geodesic dome is more than a place to stay; it's an invitation to a world of intimacy and enchantment. It's designed exclusively for couples seeking a secluded and meaningful escape. Whether you're celebrating a special occasion or simply craving quality time together, our dome is the perfect setting. Has all you need King size bed, A/C, heating, luxurious bath, modern kitchenette, private outdoor space, hot tub, fire pit and grill all yours for an unforgettable ESCAPE!

4.97 out of 5 average rating, 137 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.

4.91 out of 5 average rating, 321 reviews

Cottage in Ruckersville

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!

4.98 out of 5 average rating, 124 reviews

Monrovia on Main

Monrovia on Main is a beautifully restored gem built in 1904. Guests have use of the entire 3,400 square foot, 5 bedroom home with 3 updated full baths. Enjoy a private backyard or front porch for morning coffee or evening drinks. Walking distance to an array of shops & restaurants in downtown Orange. The home is located near Montpelier, Woodberry Forest as well as Barboursville Vineyards.

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Other great vacation rentals in Orange

5 out of 5 average rating, 61 reviews

Tatums Farmside Escape a country jewel Sleeps 10

4.92 out of 5 average rating, 36 reviews

A covered porch features several light blue chairs arranged for relaxation. Wooden flooring supports the space, while a view of the barn and surrounding greenery is visible in the background, inviting outdoor enjoyment and quiet moments.

Cabin in Somerset

Bloomingdale Honeymoon Cabin w/Mountain/Barn Views

4.98 out of 5 average rating, 91 reviews

A private in-ground pool occupies a spacious area, featuring clear turquoise water. A waterslide is positioned at one end, while a diving board is visible at the opposite side. A person can be seen swimming, demonstrating the pool's inviting atmosphere.

Home in Aroda

Sunset Retreat a cabin off the beaten path

4.98 out of 5 average rating, 99 reviews

A charming porch is seen with red rocking chairs that provide a welcoming spot. A pathway made of stone pavers leads to the porch, surrounded by lush greenery and a picnic table set in a park-like setting. Sunlight filters through the trees, creating a serene atmosphere.

Apartment in Culpeper

Red Fox Retreat

4.97 out of 5 average rating, 90 reviews

A spacious living area showcases a large sectional sofa adorned with a decorative throw and cushions. Natural light filters through wide windows overlooking the surrounding greenery. A dining area features a wooden table with chairs, complementing the cabin's rustic wooden interior.

Cabin in Madison

Relaxing 2BR CABIN, 12 acres, dog friendly, hiking

5 out of 5 average rating, 25 reviews

A charming cabin is nestled amongst tall trees, surrounded by greenery. The structure features a combination of orange and black exteriors, complemented by a spacious covered deck. A gravel path leads up to the cabin, providing access through the serene woodland setting.

Cabin in Culpeper

Campo Cibola - Brisa

5 out of 5 average rating, 28 reviews

The farmhouse features a classic white exterior with a welcoming front porch and two-story layout. Green lawns surround the house, and landscaping includes small trees and decorative plants. A pathway leads to the front door, providing a clear view of the serene surroundings.

Home in Unionville

The Farmhouse At Oak Creek Farm