Vacation rentals in Woodberry Forest

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Top-rated vacation rentals in Woodberry Forest

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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, 137 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 private hot tub is positioned on a wooden deck, inviting relaxation. The exterior of a two-story building is visible in the background, featuring a well-maintained lawn and a staircase leading to a covered porch. Soft lighting illuminates the outdoor seating area.

Apartment in Madison

4.91 out of 5 average rating, 254 reviews

The Studio at Dark Run Retreat

Quiet studio on a secluded 5 acres only 3 miles from town. Kick back and relax by the pool in the warmer months, or in the hot tub in the cooler months. Small trails lead to the creek running along the property, maybe you'll even catch a glimpse of the deer or turkey that wander thru...we've even seen a lil bear once! There is an apartment above the studio, so we ask that you be mindful of those guests if occupied. *The studio got a make-over! As of 10/6/20, we will no longer be hosting pets*

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, 271 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".

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

4.9 out of 5 average rating, 189 reviews

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.

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, 187 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!

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, 474 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, 442 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, 454 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 cabin features a welcoming front porch with a pair of white rocking chairs, providing a comfortable spot to relax. Wooden steps lead up to the porch, embraced by lush greenery and ferns, enhancing the cabin's secluded and natural setting.

Cabin in Culpeper

4.97 out of 5 average rating, 197 reviews

Comfortable and unique 1790's log cabin

Recently restored 1790's log cabin with modern amenities on a 30 acre horse farm. Secluded wooded setting with pond view, less than 1,000 feet from main house and only 5 miles from downtown Culpeper with it's fine dining and quaint shops. Take a short drive to scenic Shenandoah hiking & biking trails, local vineyards and distilleries, Civil War sites, Commonwealth Equestrian Park, stroll around the farm or just unwind on the front porch or in front of the wood stove with a good book.

Superhost

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

4.93 out of 5 average rating, 141 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

The exterior of The Little House is illuminated at dusk, highlighting the screened-in porch furnished with rocking chairs. Soft lights adorn the porch, creating a welcoming atmosphere surrounded by greenery and blooming flowers.

Tiny home in Gordonsville

4.99 out of 5 average rating, 127 reviews

The Little House: Screened Porch + Pasture Views

Are you looking for a relaxing getaway weekend in Virginia's countryside? Welcome to The Little House! This tiny house (~300 sq ft) is located on five acres overlooking a private pasture in the scenic countryside of Gordonsville. Located just a 3-minute drive from downtown Gordonsville, the home is the perfect launching point to some of Central Virginia's best wineries, historic sites, and area attractions.

Top guest favorite

A restored two-story home features a light gray exterior with blue shutters and a large front porch. Lush foliage surrounds the walkway, which is composed of natural stone. Several windows allow ample light, and hanging plants add a touch of greenery to the entrance.

Home in Orange

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.