Cottage holiday rentals in Orange County

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.

Cozy Country Cottage

This renovated "Cozy Country Cottage" that has just been remodeled 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 !

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!

Charming Guest Cottage at Winery

Early Mountain Vineyards' charming Guest Cottage, nestled next to our front block of grapevines and below our historic hilltop barn, offers breath-taking views of the Blue Ridge Mountains and a serene place to watch the sunset while sipping wine. Only short distance to our Tasting Room - open 5 days a week, Thursday - Monday. We recommend a reservation in advance - this can be made via our website, Early Mountain Vineyards, or by calling our winery directly.

'Pond House' on Huge Horse/Cattle Farm

Our Pond House is on the shore of one of the most beautiful ponds you can imagine, in the center of our 600 acre farm. Great for young families. Fishing, swimming hole, trails, horses, cows, wildlife, rope swings, hot tub, Game Barn, peace & quiet. A number of state citation bass have been caught and released from the pond, and the cane-pole fishing is great as well. 35 min. to Monticello, 15 min. to Montpelier; 6 wineries; Great restaurants.

A Charming Cottage on a Country Estate

Located on an 11-acre farm in the midst of Central Virginia’s wine country, the Cottage at Spotswood Lodge is a sanctuary for all who visit. The Cottage’s rustic charm speaks to its bygone days as the caretaker’s home for the original farmhouse, now known as Spotswood Lodge. Enjoy exclusive private access to this beautiful property by renting the Cottage (sleeps up to 7 guests and is equipped with a kitchenette - fridge/microwave only).

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!

Country Cottage with Modern Amenities

Looking for a relaxing weekend getaway in Virginia's countryside? Welcome to the Shade Tree Cottage! This home dates back to the Civil War and is full of cottage vibes. Located just a 3-minute drive from downtown Gordonsville, the home is the perfect combination of rural retreat and launch pad to some of Central Virginia's best wineries, historic sites, and attractions.

Cheerful 4Br Water View Lakehouse with Dock & More

A tranquil water view home on 2 acres with lots of amenities: large recreation room with pool and other games, hot tub, sauna, huge deck with BBQ grill, dock in the common area (5 min walk/ 1 min drive), open-space family room, fast internet and a workplace with a monitor, and more. Great for fun and work.