Vacation rentals in Gordonsville

4.87 out of 5 average rating, 349 reviews

A charming historic bungalow is presented, featuring white siding, green shutters, and a central door. Flanking the entrance are two wooden chairs set on a stone pathway. A large tree casts a soft shadow, complementing the clear blue sky and grass surrounding the home.

Cabin in Gordonsville

18th Century Charming Bungalow #127 Pool & Spa

Escape & unwind from city life on a beautiful historic, 250 acre estate 20 minutes from Charlottesville! Our historic bungalow is perfect for those who want to take a step back in history and enjoy the wonder nature has to offer! Steep stairs access the upstairs bedroom, 2 can sleep downstairs. We are only 20 min away from Jefferson's "Monticello" & from James Madison's " Montpelier". Treat yourself to an onsite certified massage with a wellness therapist.Please book online at Spagreensprings.

A single-story ranch-style home is showcased with a well-maintained lawn and manicured landscaping. The exterior features a combination of grey brick and white trim, highlighted by large windows and an inviting porch. A tree stands nearby against a clear blue sky.

4.97 out of 5 average rating, 115 reviews

The Ranch at Wine Country - Complimentary bottle

Welcome to The Ranch at Wine Country located in the heart of charming historic Gordonsville, VA. The Ranch provides all the essential amenities (condiments, tea & coffee, blow dryer, towels & much more) and some to enjoy your time away whether it be for work or play! The Ranch is pet friendly w/ a large comfy dog bed and water & food bowls. The Ranch is just minutes from UVA, Monticello and Fork Union Military Academy. Enjoy private parking, eye catching décor and a complimentary bottle of wine!

5 out of 5 average rating, 274 reviews

A newly constructed guesthouse features a charming exterior with a sloped red roof and white trim. A covered balcony with a red umbrella overlooks landscaped gardens. Stone pathways and greenery surround the home, enhancing the inviting outdoor space.

Guesthouse in Orange

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".

Guesthouse in Gordonsville

The exterior of La Petite Maison showcases a charming guest house with a large screened porch, surrounded by vibrant flower beds. A turquoise umbrella shades a lounge chair next to the seasonal in-ground pool, providing a relaxing outdoor space.

4.91 out of 5 average rating, 185 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.

4.98 out of 5 average rating, 189 reviews

The entrance features double wooden doors that open to a welcoming interior. A 'hello' mat is placed on the threshold, and two stylish chairs are positioned on the balcony above, inviting guests to enjoy the view. Lush plants accentuate both sides of the entrance.

Apartment in Somerset

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!

Apartment in Gordonsville

The entrance features a solid wooden door with glass paneling, displaying the name 'Main Street Airbnb.' A decorative yellow wreath adorns the door, and vibrant flowers are planted near the base, enhancing the welcoming appearance of the entryway.

4.97 out of 5 average rating, 482 reviews

A private apartment with Self Check-in.

This newly renovated one bedroom apartment is in the heart of the historic district of 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.

4.99 out of 5 average rating, 446 reviews

A charming green cottage is presented, featuring a small front porch with two chairs and potted flowers. Large windows allow natural light to fill the space, while the surrounding landscape includes grassy areas and trees, providing a peaceful rural setting.

Bungalow in Orange

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.

4.96 out of 5 average rating, 459 reviews

A living area features a comfortable gray sofa and armchair, set on a light area rug. A wooden coffee table is centrally located, while a TV sits on a decorative stand. Natural light enters through a window, complemented by soft lighting from a chandelier above.

Cottage in Orange

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!

5 out of 5 average rating, 181 reviews

A view from an open doorway reveals a covered porch with white rocking chairs. A welcome mat lies on the wooden floor, leading to a scenic landscape of rolling hills adorned with autumn foliage. A glimpse of black chairs is visible in the distance.

Cottage in Gordonsville

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.

4.97 out of 5 average rating, 151 reviews

A modern cabin-style home is nestled among tall trees, showcasing a sleek black exterior. A spacious screened-in porch is visible, supported by a deck with steps leading down to a gravel path. Large windows enhance the connection with the natural surroundings.

Home in Orange

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.

4.9 out of 5 average rating, 116 reviews

A cozy living space features a queen bed with a light-colored coverlet, accompanied by a small sofa adorned with red cushions. A wooden coffee table and a black chair enhance the inviting atmosphere, while natural light filters through two windows, illuminating the room.

Apartment in Troy

Black Cat Retreat

Private entrance. upstairs, Lots of light, Wrap around deck! Full private bath in room. Large room with a small kitchenette. Refrigerator, microwave and coffeemaker a kitchen sink and induction burner to cook on. Also washer and dryer in the room. Upon your arrival there will be Banana Nut Bread, fruit & filtered water. All cotton sheets on the queen size bed (plus for the full size air mattress in room.) Cotton towels, shampoo, blow dryer, iron and ironing board.

Guesthouse in Gordonsville

A charming guest cottage is set amidst greenery, featuring a welcoming front porch with white railings. Stone steps lead to the entrance. An inviting garden surrounds the cottage, complemented by decorative landscaping and trees in the background, creating a serene outdoor environment.

4.96 out of 5 average rating, 103 reviews

Gordonsville Guest Cottage - private studio

Welcome to the Gordonsville Guest Cottage, located in historic Gordonsville, VA. This is the perfect escape into small-town living, with all the necessities nearby. Close to numerous vineyards and historic sites. Relax and unwind in this 300 sq ft private guest house which includes a queen bed, living area, bathroom, and kitchenette. This cottage is in our backyard and next to train tracks. You will need to walk 150 ft from dedicated parking. No pets.

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Other great vacation rentals in Gordonsville

5 out of 5 average rating, 16 reviews

The studio apartment features hardwood flooring, with a spacious arrangement including a king bed, a cozy sofa, and a dining table. Natural light enters through large windows, and a ceiling fan adds functionality to the serene space.

Guesthouse in Troy

Memas Place Close to multiple Vineyards

Guest suite in Barboursville

An outdoor patio is shown, featuring a dining table surrounded by cozy seating. Soft lighting illuminates the area, enhancing the view of trees silhouetted against a sunset sky. Papers and snacks are placed on the table, inviting relaxation.

4.92 out of 5 average rating, 53 reviews

Nancy's Cottage - Charlottesville

Farm stay in Gordonsville

A cozy living area includes a light-colored sofa adorned with a soft throw. A round wicker storage stool sits in front, complemented by a textured area rug. Large glass doors lead to an outdoor deck, framed by flowing curtains.

5 out of 5 average rating, 13 reviews

Lovers Lane FarmStay Studio

A charming cottage is illuminated in the evening light, showcasing a welcoming entryway with yellow glow. The lawn is green and well-maintained, bordered by shrubs and trees, with a glimpse of outdoor seating visible near the entrance.

5 out of 5 average rating, 66 reviews

Wine Country Cottage, Hot Tub, Game Room, Slps 12

5 out of 5 average rating, 19 reviews

A modern black exterior structure is set amidst a wooded landscape, featuring large windows that illuminate the interior. A hot tub and fire pit are positioned on a patio, with a seating area composed of wooden chairs inviting outdoor relaxation. Gentle dusk light enhances the serene atmosphere.

Home in Culpeper

The Reserve

4.99 out of 5 average rating, 86 reviews

Clifton House | An Equestrian Getaway

5 out of 5 average rating, 46 reviews

A two-story building is showcased, featuring a light-colored exterior with a stone accent at the base. A wooden deck is visible, leading to an entrance on the upper level. Two garage doors are prominently displayed beneath the deck.

Apartment in Orange

Apartment in Orange, "Farm Sweet Farm"

A modern kitchen is presented, featuring light cabinetry and sleek stainless-steel appliances. A dark granite countertop extends over the kitchen island, offering a defined workspace. Natural light enters through a nearby window, illuminating the open layout while cabinets provide ample storage.