Holiday rentals in Gordonsville

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Top-rated holiday rentals in Gordonsville

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Guest favourite

Guest house in Orange

5.0 out of 5 average rating, 183 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.

4–11 Mar

$161 SGD per night

Guest favourite

Tiny home in Gordonsville

4.94 out of 5 average rating, 116 reviews

Glamping Cabin, Gorgeous Views, Sunsets! 1

Sunsets, Stargazing, Fireflies, Dogwoods, Peonies, Organic Berries, Wild Flowers. Everyday the views are spectacular, day or night. Big thanks to our previous guests for so many terrific reviews! Even with no electric, everyone has been thrilled with our Glamping experience. We make getting outside easy and super comfy! With a Tempurpedic style bed, propane heater, plenty of solar lights, fire pit, wood & kindling, fresh spring water, private Loo and shower house, you won't want to leave.

26 Sep – 3 Oct

$128 SGD per night

Guest favourite

Guest house in Gordonsville

4.91 out of 5 average rating, 171 reviews

La Petite Maison at Hedgeapple Hollow

La Petite Maison (our guest house) is the perfect place to simply get away from the hustle and bustle and relax! Sit in the private screen porch and watch the sun melt into the mountains. Deer, hummingbirds, bluebirds, and the occasional turkey like to hang out on the 8 acres of the property, perfect for any wildlife lover. Enjoy the fenced in common area featuring a seasonal in-ground pool. Conveniently situated near award-winning wineries, Montpelier, and historic downtown Gordonsville.

4–11 Aug

$198 SGD per night

Guest favourite

Bungalow in Orange

4.98 out of 5 average rating, 363 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.

4–11 Mar

$196 SGD per night

Guest favourite

Cottage in Orange

4.95 out of 5 average rating, 367 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!

12–19 Jan

$149 SGD per night

Guest favourite

Flat in Gordonsville

4.99 out of 5 average rating, 371 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.

15–22 Jun

$140 SGD per night

Guest favourite

Cottage in Gordonsville

5.0 out of 5 average rating, 127 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.

12–19 Dec

$211 SGD per night

Guest favourite

Cottage in Gordonsville

4.79 out of 5 average rating, 251 reviews

Historic, Quaint Bungalow pool & wi-fi

Escape & unwind from city life on a beautiful historic, 250-acre estate 20 minutes from Charlottesville! Our historic bungalow comfortably fits 4-6 people and is perfect for those who just want to take a step back in history and enjoy the wonder nature has to offer! For outings we are only 20 min away from Jefferson's "Monticello" & 35 min from James Madison " Montpelier". Play golf 5 min away at Spring Creek Golf. Treat yourself to an onsite certified massage wellness therapist.

1–8 Aug

$190 SGD per night

Guest favourite

Guest suite in Charlottesville

4.94 out of 5 average rating, 121 reviews

The Brothers Great Room

Your private guest suite is located in Northern Albemarle County Virginia. We are just off of Route 29 with easy access to local venues. The suite is on the 2nd floor, up one flight of stairs. Albemarle County is central to the University of Virginia, Monticello, Montpelier, and nearby Shenandoah National park. There are many wineries, craft beer breweries, and wedding venues in the area. Your four legged friends may run the open areas. Please clean up after your pet.

18–25 Jul

$101 SGD per night

Guest favourite

Bungalow in Gordonsville

4.98 out of 5 average rating, 387 reviews

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.

5–12 Jun

$279 SGD per night

Guest favourite

Farm stay in Barboursville

4.98 out of 5 average rating, 177 reviews

Moonfire Farm cozy Shenandoah Region Getaway

Experience charm and nature at Moonfire Farm! Our finished basement on a 5-acre hobby farm offers delightful animal encounters with chickens, ducks, alpacas, and hilarious goats. Our active family of three, including our 7-year-old daughter Piper, welcomes you. High-speed Internet and nearby wineries, breweries, hiking trails, and pick-your-own fruit locations await you. Explore our guidebook for recommendations. Book now for a memorable farm getaway!

29 Oct – 5 Nov

$185 SGD per night

Guest favourite

Flat in Barboursville

4.81 out of 5 average rating, 191 reviews

Burnley Beauty Apartment

Renovated private basement apartment located in Barboursville wine country! Relax out where it’s silent and you won’t hear any traffic. We are just a short drive to town where you can enjoy points of interest such as UVA, Monticello, wineries, breweries, and shenandoah parkway! We are happy to host and help accommodate our guests! We are animal lovers so check out our guidebook or ask us if you need pet friendly recommendations.

14–21 Jul

$101 SGD per night