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Vacation rentals in Woodberry Forest

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Top-rated vacation rentals in Woodberry Forest

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Home in Orange

4.83 out of 5 average rating, 273 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

Guesthouse in Orange

5 out of 5 average rating, 229 reviews

Taj Garage Guesthouse

Newly constructed (2021) above garage guesthouse with private, self check-in entrance, off-street parking, located among historic homes just 4 blocks to restaurants, shops, park and art galleries in downtown Orange. Guesthouse includes a fully equipped kitchen, queen bed, full bath, seating area, TV, wifi and balcony. Handcrafted heart pine furniture. Level 2 EV Charger. Kitchen includes refrig, stove, microwave, toaster and Keurig. Close to superb wineries, breweries and historic sites.

Serviced apartment in Somerset

4.99 out of 5 average rating, 170 reviews

Newly Renovated•Private Farm Apartment near Cville

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!

Bungalow in Orange

4.99 out of 5 average rating, 400 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.

Cottage in Orange

4.95 out of 5 average rating, 411 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!

Home in Robertson

4.92 out of 5 average rating, 204 reviews

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.

Rental unit in Gordonsville

4.98 out of 5 average rating, 423 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.

Cottage in Gordonsville

5 out of 5 average rating, 154 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.

Farm stay in Brightwood

4.96 out of 5 average rating, 122 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.

Guesthouse in Madison

4.97 out of 5 average rating, 242 reviews

Hebron Valley Cottage

Nestled in the scenic Hebron Valley, this 2 bedroom 1 bath cottage is the perfect getaway from busy, city life. The cottage offers panoramic views of the Blue Ridge Mountains, including Old Rag and is located near several wineries, breweries, restaurants, antique shops, hiking trails and historic sites. The cottage is 3 miles from the town of Madison and is convenient to Charlottesville, Culpeper and Orange.

Cottage in Madison

4.99 out of 5 average rating, 146 reviews

Fishback Cottage, Central location

Centrally located in the country side of Madison, VA. With easy access to route 29 and closely located to local breweries, wineries and hiking. Speedy wifi makes it easy for a business trip or for a night of relaxation with Netflix. 7 Min Drive to Renback Barn or Early Mountain Vineyards 17 Mile Drive to White Oak Canyon or Old Rag trails 25-30 Min Drive to Charlottesville or Culpeper

Guest suite in Reva

4.95 out of 5 average rating, 109 reviews

Ridgeview Retreat Log Cabin - Hiking, Wine, UVA

Entire main floor of quaint log cabin in the heart of Virginia's Wine Country. Close to Charlottesville airport, UVa campus, Shenandoah National Park, wineries, breweries, local restaurants. 2 bedroom, 2 bath with a 3rd bedroom at additional cost. Access to laundry. Cozy front porch, tons of parking, screened in porch out back for dining or relaxing.

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Popular amenities for Woodberry Forest vacation rentals

Free parking on premises

Air conditioning

Other great vacation rentals in Woodberry Forest

Home in Orange

5 out of 5 average rating, 14 reviews

1930's Orange Bungalow

Guesthouse in Barboursville

4.98 out of 5 average rating, 40 reviews

Burnley Cottage

Rental unit in Culpeper

4.99 out of 5 average rating, 71 reviews

Red Fox Retreat

Home in Aroda

4.97 out of 5 average rating, 78 reviews

Sunset Retreat a cabin off the beaten path

Home in Orange

4.94 out of 5 average rating, 16 reviews

Family Retreat in Orange

Home in Madison

5 out of 5 average rating, 50 reviews

Winter is beautiful.

Guesthouse in Orange

4.93 out of 5 average rating, 15 reviews

The Revelry Fields Bungalow

Rental unit in Orange

5 out of 5 average rating, 28 reviews

Apartment in Orange, "Farm Sweet Farm"

Destinations to explore