Vacation rentals in Madison Mills

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Top-rated vacation rentals in Madison Mills

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Guest favorite

Farm stay in Rapidan

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.

4.87 out of 5 average rating, 153 reviews

Top guest favorite

The image showcases a charming brick home set against a backdrop of gently rolling farmland. A group of cattle is seen grazing in the distance, while a large tree provides shade in the foreground. The clear blue sky enhances the serene countryside view.

Home in Orange

Tatums Farmside Escape a country jewel Sleeps 10

Relax & enjoy gorgeous views of farmland, mountains and grazing cattle. Perfect for multifamily stays, wedding parties, vacations.. Short drive to Orange & Culpeper. Near wineries such as Early Mtn , Prince Michelle, Barboursville etc. Historic areas near such as Montpelier. Visit local breweries Bald Top and Iron Pipe. Madison County borders the Shenandoah Nat Park where you can hike, fish & site see. Your stay includes coffee, toiletries, firewood, linens and towels. FIREFLY FAST INTERNET!

5.0 out of 5 average rating, 90 reviews

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

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".

5.0 out of 5 average rating, 319 reviews

Guest favorite

A charming single-story house is presented with a light-colored exterior and dark shutters. Rocking chairs are positioned on the front porch, inviting relaxation. A well-maintained lawn surrounds the home, and a backdrop of trees complements the serene setting.

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.

4.9 out of 5 average rating, 230 reviews

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

Cozy Farm Apt near Cville•hot tub, sauna, mt views

Come experience a relaxing getaway on our family’s dairy farm in Somerset. In beautiful Orange County, We are close enough to Charlottesville (25 min) for all your shopping and eating needs, but has 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!

4.98 out of 5 average rating, 224 reviews

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

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.

4.99 out of 5 average rating, 503 reviews

Guest favorite

Home in Orange

Stone Bridge Farm - 1 BR Riverfront ADA Apartment

This private apartment is part of a historic 1882 riverfront estate, offering comfort, accessibility, and peaceful surroundings. Ideal for solo travelers, couples, extended stays, or guests attending events nearby who want independence and ease of access. * Private entrance and parking * Kitchenette and sitting area * Designed to meet most ADA guidelines * Accessible bedroom, kitchenette and bathroom with transfer shower chair available * Quiet, private setting within a larger estate

5.0 out of 5 average rating, 5 reviews

Top guest favorite

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!

4.95 out of 5 average rating, 514 reviews

Guest favorite

An open living area features high wooden ceilings with exposed beams, creating a spacious atmosphere. A large kitchen island with bar seating is situated near a dining table. Two spiral staircases lead to upper levels, while large windows frame views of the surrounding nature.

Home in Robertson

One Of A Kind Home in VA Wine Country on 50 acres

Welcome to Lumusa Lodge. Leave your cares behind as you turn onto the windy road that leads you to this beautiful 50-acre retreat. We are proud to share our home and hope your time here is rejuvenating. Designed/built by a Hollywood actor and situated in wine country, this home is an hour from Dulles, 45 minutes from Charlottesville & 15 minutes from Culpeper. We have an adjacent farmhouse if you need additional space. Great venue for weddings, bachelorettes, and other special events.

4.93 out of 5 average rating, 258 reviews

Top guest favorite

A modern two-story home features a light grey exterior and black shutters accenting the windows. A welcoming front porch is visible, with white railings and a small lamp. The two-car garage displays a double door, while a neat driveway leads up to the entrance.

Home in Orange

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.

4.96 out of 5 average rating, 45 reviews

Guest favorite

An open-plan kitchen and living area is showcased with wooden beams and large windows, allowing natural light to illuminate the space. A kitchenette features wooden cabinetry, a microwave, and a small dining bar with three tall stools. A rocking chair is positioned beside a window overlooking the woodland.

Farm stay in Brightwood

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.

4.94 out of 5 average rating, 174 reviews

Top guest favorite

The cottage is set amidst lush greenery, showcasing a charming exterior with a light-colored facade and a metal roof. Adjacent to the porch, two rocking chairs frame the entrance, while neatly trimmed shrubs and vibrant flowers enhance the welcoming atmosphere.

Cottage in Orange

Cozy Country Cottage

"Cozy Country Cottage" is a rare find. It's located in a quiet neighborhood surrounded by beautiful farmland. It has a self check-in entrance, parking next to house and an amazing view of sheep grazing in pasture across the road. It's close to wineries, breweries, historic sites such as Mount Pelier, Monticello which is 23 miles, Woodberry Forest School which is 10 mins. away, shopping, hiking and more. Come and enjoy the quite, peaceful country !

4.94 out of 5 average rating, 101 reviews