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Places to Stay

Orange/Gordonsville, VA

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Nathanial Inn Gordonsville VA

The Nathaniel Inn is located in Historic Gordonsville. A quaint town just north of Charlottesville, Virginia. The Inn provides a unique experience by offering you the hospitality of boutique hotel with the privacy of a vacation rental to serve your central Virginia travel needs. The Inn consists of the Nathaniel House which contains three suites and the next-door Gordon Cottage which can be reserved as individual suites or all together allowing maximum flexibility to fit your group. 


Keswick Hall 

Keswick Hall has been an icon of the Virginia countryside for over one hundred years. In order to preserve this landmark estate, co-owners Molly and Robert Hardie have partnered with some of the most coveted purveyors to bring Keswick Hall into the future whilst paying homage to its storied past. Set amid a backdrop of Virginia’s natural splendor, our newly reimagined resort invites guests and locals to discover a sense of discrete luxury where you can retreat from the everyday into the calm comforts of a space all your own.

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Airbnb Gordonsville Charming One Level Home! Spacious & Private!

Custom One level home on 6 acres w/SW Mountain views & high speed Internet on scenic 231 byway just minutes to downtown Historic Gordonsville. Enjoy relaxing on the covered front porch or back patio w/fire-pit! The spacious updated home has 2 fireplaces, 3 bedrooms, a large den, 3 full baths, 2 living rooms, gorgeous kitchen w/SS appliances, large dining area , laundry room and sleeps 8-10 guests.


Antique Log Cabin Near Charlottesville & Wineries | Sauna Just Installed!

Antique log cabin C. 1810, recently relocated and lovingly restored. We are approximately 20 miles from Charlottesville, local to numerous wineries, and 38 miles from Massanutten Ski Resort. Here you can enjoy a rustic getaway, with all of the modern features you need to be perfectly comfortable. You will find yourself surrounded by an abundance of wildlife: Deer, Turkey, Foxes, Eagles, Osprey, Herons and more (a bird-watcher’s paradise!). Look out the window and be met with top notch country views- 110 acres of rolling pastures, pristine ponds, and marked walking trails. If you plan to use the trails or ponds, let us know and we will be happy to give you a tour upon arrival! Our trout pond was stocked on 11/9/22 with 150+ Rainbow and Brook trout, averaging between 2-5 lbs. Watch the video tour to see a clip of the release! Many citation fish are caught from our ponds annually. A sportsman's delight!

While pets are generally discouraged, we are pet tolerant depending on the age, size and breed of the animal.

Be amongst the first to enjoy our newly installed sauna!

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Boxwood Villa

Located just outside the town of Orange, Virginia, The founders of Grelen Nursery &
The Market at Grelen renovated this lovely 1891 property to add to their event & lodging options for their Market at Grelen guests and area visitors. In good shape structurally, this gem is set on 13.6 beautiful acres and boasts modern amenities and a .5 walking trail. Named for its large boxwood circling the house, Boxwood Villa is surprisingly private given that it's within walking distance to town.

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Elmwood House

Find yourself surrounded by lush acreage & privacy in this fantastic home. Elmwood House is more than ready to assist in making the best memories with loved ones. You will feel as if you are secluded and away from it all. Step outside under the mature hardwoods and enjoy incredible views & the horses grazing.

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The Ranch at Wine Country - Complimentary bottle

Your recently, fully remodeled and fully furnished 1972 Kingsbury Ranch home is going to be your new home away from home! Enjoy 3 bedrooms and 1.5 bath with gorgeous décor (most handmade by your host) and cozy country feel with a relaxing fully furnished carport turned oak wooden den to enjoy the natural gas fire place along with wine cooler, complimentary bottle of wine and flat screen tv. Relax, unwind and pull up a seat... we are glad to have you!


Inn at Willow Grove

A peaceful garden setting, luxury appointments and timeless Southern charm and décor come together to set The Inn at Willow Grove among the best and most unique hotels in Virginia Wine Country.

Befitting our historic heritage, no two rooms are the same. Each of our 25 rooms and suites has been individually furnished and decorated to offer a completely unique experience. What they share are locally inspired design touches, antique flourishes and every luxury imaginable, plus a few that aren’t.

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Comfort Inn Orange VA

Property Location With a stay at Comfort Inn & Suites Orange - Montpelier, you'll be centrally located in Orange, within a 10-minute drive of Montpelier and James Madison Museum. This hotel is 28 mi (45.1 km) from Monticello and 28.2 mi (45.3 km) from Virginia Discovery Museum. Rooms Make yourself at home in one of the 58 air-conditioned rooms featuring refrigerators and microwaves. Complimentary wireless Internet access is available to keep you connected.

Reservations can also be made by calling the Hotel Front Desk at (540) 672-3121 and mentioning Central Virginia Wine Tours and Transportation. Email reservations can also be made by sending us a message at

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Mayhurst Estate

One of Virginia's most beautiful Italianate and Victorian style homes. Mayhurst is over 9,500 square feet, 5 levels, has 14 fireplaces, and over 36 acres of trails, grounds, and beautiful spaces to relax and unwind after a great day of exploring. Mayhurst was built in 1859 by President James Madison's great nephew and has been home to much history over the years.  Mayhurst has 8 beautiful guest rooms with each having its own style and story.  Mayhurst offers a gourmet breakfast each morning as well as a host of other amenities to our guests.  Come and enjoy one of Virginia's most beautiful gems.

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The Gordon Cottage

Welcome to the Gordon Cottage! Located on Main St in Gordonsville, about 30 mins north of Charlottesville, Va., the cottage is a great base of operations for all your central Virginia travels including, Monticello, Montpelier, Ashlawn, UVA and the surrounding wineries, breweries and distilleries. The cottage is renovated throughout and is a comfortable and cozy place for your vacation. We are an easy walk to downtown Gordonsville for nearby restaurants and shops!

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Pillow Talk Airbnb Gordonsville

Well Hung Vineyard Restaurant Cottage “Pillow Talk”
Conveniently located in the heart of downtown Gordonsville, this newly renovated home offers 2 bedrooms w/ queen beds, full bathroom and ½ bath, full kitchen, office space, living room, and washer & dryer. High speed internet, keyless entry, private driveway & street parking available.


Gordonsville Getaway Airbnb

Welcome to the Gordonsville Getaway, located in historic Gordonsville, VA. This is the perfect escape into quiet, small-town living, with all the necessities nearby. Close to numerous vineyards and historic sites. Relax and unwind with three bedrooms, a full kitchen, front porch and backyard for you to enjoy. One-level home, with high speed internet. Located near train tracks; you may occasionally hear a whistle during the day. Grocery, shops & restaurants are within walking distance.

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Shenandoah Crossing

Rooms Make yourself at home in one of the 115 guestrooms. Complimentary wireless Internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms have hair dryers and toothbrushes and toothpaste. Conveniences include coffee/tea makers and irons/ironing boards, and housekeeping is provided weekly.

Amenities Dip into one of the 2 outdoor swimming pools or enjoy other recreational amenities including a sauna and a fitness center. Additional features at this hotel include complimentary wireless Internet access, concierge services, and gift shops/newsstands.

Dining Grab a bite from the grocery/convenience store serving guests of Bluegreen Shenandoah Crossing, Ascend Resort Collection.

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Spotswood Lodge Rental

Located in beautiful Somerset, VA, Spotswood Lodge is an 11-acre farm house & cottage rental. Operated by The Market at Grelen, it is open to couples who are getting married at Grelen or any of the other amazing venues in the Orange County area.  With eight bedrooms and seven full baths, it’s a wonderful option for wedding parties and/or families of the bride and groom.   Of course, weddings are not the only reason to consider renting The Lodge.  If you’re looking for a place for a family reunion, company retreat or just searching for the perfect country getaway, look no further.


The Inn and Tavern at Meander

The essence of Virginia … Romantic, historic 1700s country inn and restaurant offers elegant accommodations, acclaimed fine dining, extensive Virginia wine list, gracious setting and warm hospitality. 10 stunning guest accommodations await your pleasure at the Inn at Meander Plantation 2333 N. James Madison Hwy, Locust Dale, VA 22948, Phone:540-672-4912

Wolf Trap Farm Vacation Rental 

Wolf Trap Farm offers Vacation Rental and limited Bed & Breakfast accommodations on a 584 acre horse and cattle farm, with mountain views, miles of forest trails, rolling pastures, abundant creeks and brooks, nine ponds, and easy access to all the attractions of Charlottesville and the Central Virginia area.

Charlottesville, VA

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200 South Street Inn 

The 200 South Street Inn offers old-world elegance in the middle of the lively historic downtown of Charlottesville, Virginia. The Inn combines two restored houses, the larger house, and the smaller house, together becoming an unforgettable Charlottesville Inn. 

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Airbnb Country Retreat for Family and Friends

Welcome to the beautiful countryside around historic Charlottesville!
"The Tree" House so named for its massively gorgeous oak, stands at what once was the site of a pre-Civil War cabin. This home welcomes visitors old and young alike and groups large or small! Explore the spacious outdoors that include hiking trails, a clay tennis court, quaint pond with a floating dock, a fire pit and tire swing and a large field for lacrosse, soccer, football, frisbee - you name it!

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Omni Hotel Charlottesville

Adjacent to the historic downtown Pedestrian Mall, the Omni Charlottesville Hotel blends the area’s unique history with modern luxury. Relax in our seven-story glassed in atrium lobby, lounge in one of our heated pools, or unwind in contemporary guest room accommodations featuring a host of amenities designed to make your visit unforgettable. If you’re in town to visit the University of Virginia, Omni Charlottesville Hotel is near the campus.


Residence Inn Marriott 

The 200 South Street Inn offers old-world elegance in the middle of the lively historic downtown of Charlottesville, Virginia. The Inn combines two restored houses, the larger house, and the smaller house, together becoming an unforgettable Charlottesville Inn. 


Draftsman Hotel

Designed with a curator’s touch, The Draftsman, Charlottesville, University, Autograph Collection Hotel, Autograph Collection celebrates the spirit of Virginia’s original voices with a nod to its dynamic present. From the stylish, boutique hotel accommodations to the local artwork, every aspect is meticulously crafted to ensure relaxation and invigorate the spirit. Striking an artful balance of tradition and innovation, The Draftsman, Charlottesville, University, Autograph Collection Hotel is a beacon of upscale comfort in downtown Charlottesville, VA.

Madison, VA


The Hill of Content is located near the post office of Radiant, Virginia. It is near to the towns of Orange and Madison and not very far from Culpeper and Charlottesville, Virginia.  The name reflects upon the sense of peace and solitude that we discovered at the property.  Certainly guests can find some peace and quiet on the property.  We are very close to Woodberry Forest School for visitors to that campus and not far from the historic home of James and Dolley Madison, Montpelier.  To the west are the Blue Ridge Mountains and Skyline Drive.  The Town of Madison is just up the road and offers some interesting and historical stops.  The Town of Orange is nearby with antique, knick-knack shopping and food and beverage on offer.  A bit further south is Charlottesville and the University of Virginia, about a 45 minute drive.    

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Woodbourne Estate, circa 1810, is a National and Virginia historic registered landmark Manor House and farm nestled in the foothills of the blue ridge mountains in Madison, Virginia. The 53-acre Estate is also home to our award-winning Bald Top Brewing Company which sits just a comfortable stroll beyond the Manor house. This magical Manor, with its gorgeous grounds, gardens, barns, ruins, pool, stream and vistas awaits! The Manor at Bald Top: Drink in the Moment!


Chestnut Oak Farm is a luxurious western-style lodge retreat on a 90 acre horse farm near the base of Old Rag Mountain. The lodge was constructed in 2009 using granite blocks from the farm and huge Virginia pine logs in a western style of rustic elegance. The lodge is surrounded by decks and porches to take in the magnificent view over Hidden Valley, Old Rag Mountain, the farm's twin ponds, and the horses grazing in the fields. The lodge is equipped with a Chef's Kitchen, huge dining room (we have seated sixteen), double-sided fireplace, baby grand piano, screened porch, and covered porch. The main lodge house has three Master Bedrooms, and two other large bedrooms with a shared bath. Downstairs is a walkout game room with foosball, ping pong, bar, and a fire pit/movie pit with 52' screen TV. The outdoor 8 person hot tub is steps away, overlooking the pond.

Culpeper, VA

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More house than hotel, West Park Gardens was built in 1921 and offers travelers a unique vibe focused on comfort and relaxation. Downtown restaurants and shopping are an easy walk from the house. Choose from three luxury guest rooms or rent the entire house. Either way, you have access to the living room, dining room, game room, fully stocked kitchen, and backyard garden. Rates are all-inclusive. West Park Gardens is pet friendly and provides 24-hour keycode access.

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Inspired by Thoreau’s Walden, Walden Hall is a luxury Bed and Breakfast and event space nestled in the foothills of the Blue Ridge Mountains. This beautiful home sits on 10 acres of rolling farmland in the tranquil countryside of Reva, Virginia; the perfect setting for a romantic getaway, family gathering or memorable Virginia wedding.

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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 with you. Designed/built by a Hollywood actor, this unique home is the perfect getaway. Situated in the middle of wine country, this home is an hour from Dulles, 20 minutes from the VRE, 45 minutes from Charlottesville & 15 minutes from downtown Culpeper.

Lake Anna, VA

Afton, VA

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Afton Mountain Vineyard Retreat is the perfect way to celebrate a romantic weekend or just a relaxing getaway!  This two bedroom, two bath cottage is located in the heart of a beautiful mountain vineyard.  the views that surround this property are breathtaking.  Situated on the sunrise side of Afton Mountain, this property sits at 1000 feet in elevation.  Enjoy sprawling views of grapevines out your back door and the panoramic mountain view. 

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The Inn at Blue Mountain Brewery is the ideal place to gather with family and friends. This whole-house rental comfortably sleeps up to 12 guests. 

Conveniently located on Route 151 in scenic Nelson County, the Inn is minutes away from some of the area's best wineries, breweries, cideries, and distilleries, and a quick 20 minute drive to the University of Virginia in historic Charlottesville, Virginia. 20 miles to the south, Wintergreen Resort offers a variety of ski, spa, golf, and various recreational options year-round. Numerous hiking trails, state and national parks are also in the nearby vicinity.

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Nestled in the foothills of the Blue Ridge Mountains on the Nelson-151 Brew / Wine Trail you will enjoy the peace and serenity of our private escape.  Whether you’re here to enjoy the beautiful wineries and breweries surrounding Charlottesville or skiing at Wintergreen Resort, we guarantee lasting memories.    

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