Holiday rentals in Orange County

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".

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 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!

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!

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.

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.

Hidden Haven

Hidden Haven is just that! A 600 square foot romantic, private, peaceful, little haven. Hidden in the woods just 6 miles outside of the Town of Orange. Open the garage door in the living area and step out on the 300 square foot screened in porch where you can relax at the firepit under the covered roof. On the porch at Hidden Haven, we like to say, "time wasted is time well spent". The romantic vibe and modern amenities make it a prefect place for a couple's getaway.

Private Couples getaway with HOT TUB.

Welcome to the exquisite location, conveniently situated only 15 minutes away from Lake Anna. Our family has invested significant effort into creating this splendid, contemporary A-frame cabin, nestled on our 110 acre family farm. Strategically positioned to offer a breathtaking view of the creek that traverses our property, this private retreat is located just one hour from Washington, D.C. Immerse yourself in the tranquil ambiance and soothing sounds of nature.

Bond House: Historic Retreat at Walnut Grove

Escape from the city to a historic 1740s cottage with a distant view of the Blue Ridge Mountains and peaceful surroundings with the opportunity to experience the slower pace of country living. Spend the day at Lake Anna to swim/ kayak/ boat or visit the state park, just 5 minutes away. Enjoy local wineries, and explore historic Civil War battlefields. After a fun filled day, return to your private oasis with a fully equipped kitchen.