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Vacation rentals in Woodridge

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Top-rated vacation rentals in Woodridge

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Guest favourite
Home in Charlottesville

Rooftop*Mountains*Lake/Near Monticello/DT/Wineries

Spacious modern house with a brand new rooftop deck overlooking Carter Mountain and Monticello. Two spacious primary bedroom suits (one on each floor) with attached decks, plus additional two bedrooms and a full bathroom on the 2nd floor. Located in a quiet neighborhood. Backs up to a lake for beautiful views from each level and tranquil environment. Convenient location - minutes away from Monticello (2 mi/4 min), downtown (2.5 mi/6 min), UVA (3 mi/9 min), wineries (3.5 mi/5 min+) & breweries.

4.98 out of 5 average rating, 133 reviews
Top guest favourite
A charming farmhouse is set on a spacious green lawn, surrounded by trees. Featuring a welcoming front porch with railings, the house displays multiple peaked roofs and large windows, inviting natural light. The grounds offer ample space for outdoor activities.
Home in Charlottesville

Thomas Jefferson Pkwy - Gateway to Monticello

Farmhouse on 14 acres offers closest proximity to Monticello (4 minutes away). Jefferson Vineyard (1 min), Ash Lawn (3 min), Carter's Mountain & Michie Tavern (5 min), Downtown Open-Air Mall (14 min). Relax with a cold drink on the front porch or enjoy views of the mountains and pond from the back deck. There is plenty of space to breathe here. Full kitchen & laundry. Feel free to snack on whatever we have. Great views & country feeling but close to everything. Relax & make yourself at home!

5.0 out of 5 average rating, 208 reviews
Top guest favourite
The exterior of the home is illuminated by soft lights, creating a warm atmosphere at night. The backyard features two swimming pools adjacent to a concrete deck with various seating options. Tall trees provide a serene backdrop to the scene.
Apartment in Palmyra

Love 2B close 2U: Quiet, comfy Apartment & Pool!

Quiet, rural setting in neighborhood culdesac. Located off Rt 53, approx 15 mins from Monticello & FUMA. Basement of home, w/private entrance is a 1000 square foot apartment with a large full bathroom, large bedroom with 2 Queen size beds, open floor plan with living, dining area and kitchen. Space includes a large screened in porch w/ bed swing, patio area & swimming pool. No diving - deep end 6ft. View of woods on back of property w/ sunrise through the trees in morning. Lovely retreat.

4.99 out of 5 average rating, 142 reviews
Top guest favourite
The cottage exterior is seen with a spacious front porch featuring two rockers and small tables. A warm glow from lights illuminates the entrance. The building showcases a sloped metal roof, charming green shutters, and potted plants on either side of the door.
Cottage in Scottsville

The Cottage at Hardware Hills Vineyard

Head for the Hills! The Cottage at Hardware Hills Vineyard sits atop the property alongside the main estate house. Bask in Virginia sunsets over the vines. Take a short hike down to the Hardware River where you can dip a toe in or try your hand at fishing. On weekends, you have a family-owned winery right in your front yard to stroll down and sit by the vines to enjoy delicious wines. Centrally located to many wine trail attractions and all that the Charlottesville area has to offer.

4.99 out of 5 average rating, 139 reviews
Top guest favourite
A scenic view of a charming road lined with historic houses. Pink blossoms from trees add color to the landscape, while power lines stretch overhead against a clear blue sky. The greenery and flowers along the roadside enhance the tranquil ambiance of the neighborhood.
Home in Scottsville

Terrell House, ca 1850

This ca 1840 house, listed on the National Register of Historic Place as part of the Scottsville Historic District, has been completely renovated. It is located in historic Downtown Scottsville. Within walking distance are four restaurants and a brewery. A grocery store and other restaurants also a short drive away. A nature area with trails is also nearby. It has a kitchen, dining and living area. WiFi. If this house is already reserved, I have other properties that could be available.

4.87 out of 5 average rating, 149 reviews
Top guest favourite
The living room features two elegant sofas flanking a glass coffee table on a natural fiber rug. A tall floor lamp provides light, while decorative artwork and a potted plant add a touch of warmth. Windows with bamboo shades allow natural light to filter in.
Cottage in Scottsville

The Butler’s Cottage At Chester

Situated on one of the six historic properties in Scottsville, Chester and its seven-acre setting evokes a feeling of serenity and charm for all those who visit. As you approach, the first sight of the white wooden fence says you are here. Skirting the fence, you get your first views of the grounds and the original Greek Revival style Manor House. The main house, built in 1847 and later expanded, still exudes the charm which would have greeted guests arriving in carriages 175 years ago.

5.0 out of 5 average rating, 114 reviews
Top guest favourite
A welcoming exterior of a curved house is presented, featuring a light stone pathway leading to a front porch. Two white rocking chairs are positioned in front, with decorative planters filled with greenery on either side. The backdrop consists of lush trees and a blue sky.
Home in Charlottesville

Unit 1_Expansive Luxury Suite for up to 4 Persons

Take a journey to Albemarle County and experience historical sites and luxurious accommodations. Sonsak is uniquely situated on the Thomas Jefferson Parkway; nears area's most celebrated landmarks, including Monticello - Home of Thomas Jefferson, directly across Michie Tavern and near Ash Lawn - Home of James Monroe, Carter Mountain Orchard and numerous Vineyards. Embark on a 'Journey Through Hallowed Ground', an unforgettable experience that's packed with history and beauty.

4.98 out of 5 average rating, 162 reviews
Top guest favourite
The cabin exterior features a wooden facade complemented by metal accents. A screened-in porch with a white door opens into the entryway, surrounded by potted plants and greenery. Stone steps lead to the porch, creating an inviting entrance.
Tiny homes in Scottsville

Convenient Rustic Cabin near Wineries

I’m located 6 miles from Scottsville, 15 miles from Charlottesville, 25-30 minute drive. A pasture of cattle is not too far away you can hear the mooing at times and see sightings of deer quite often. It’s a private and quiet location. Two large rivers, James and Rivanna offer recreational activities. Rustic cabin, country located. Clean and cozy with a well stocked kitchen with all your cooking needs. If not, leave suggestions on what is missed. Thank you.

4.92 out of 5 average rating, 292 reviews
Top guest favourite
The cottage is set in a spacious yard, surrounded by greenery. A large tree with bare branches is visible to one side. Bright pink flowers bloom nearby, complementing the exterior's muted tones. The home features a welcoming porch with white railings.
Farm stay in Palmyra

Cottage at Fruit Hill Orchard

The Cottage at Fruit Hill is nestled between our peach and apple orchards on my family’s 12 acre farm. Take a stroll through the peach blossoms, pick from our sunflower patch, enjoy some private time in the orchards during the fall, and gaze at our Christmas lights display in December. This charming cottage was originally built in the 1940’s and has recently been updated to be as comfortable for our guests as possible. Come enjoy a peaceful getaway at the orchard!

4.97 out of 5 average rating, 182 reviews
Top guest favourite
Apartment in Palmyra

The Cottage Next Door

Private and modern in a peaceful country setting near Charlottesville, Scottsville, Palmyra, Fork Union, Lake Monticello and historical attractions. The nearby James River offers rafting, floating and fishing. Scheier Natural Area, a local hiking trail, is just next door. Wineries and distilleries are a short drive away as well. While you can prepare full meals in the kitchen, there are several wonderful restaurants within a short drive, if you choose.

4.99 out of 5 average rating, 133 reviews
Top guest favourite
Home in Charlottesville

10 Vineyards Within 10 Mi, EV charger & Mini Goats

Upscale boutique Carriage House on a 25-acre farm in Charlottesville Wine Country. Minutes from top vineyards, this light-filled retreat features elegant rustic design, new furnishings, and spa-like comfort. Enjoy visits with Nigerian dwarf goats and free-ranging chickens. Perfect for romantic getaways or remote work, with WiFi, cozy touches, and the beauty of nature all around. Tesla wall connector charger available for guests.

4.97 out of 5 average rating, 140 reviews
Top guest favourite
A traditional two-story farmhouse with white siding is set against a lush green landscape. Two porches extend across the front, flanked by vibrant flower beds and well-maintained grass. The surrounding trees provide a natural backdrop, enhancing the serene rural atmosphere.
Home in Scottsville

1893 House on Wild Oats Farm

This traditional rambling farm house built in 1893 is located on a 130 acre working cattle farm in lovely rural Virginia. Enjoy your morning coffee with views of the pastures, pond and woods from 3 porches. The farm is conveniently located to Scottsville, Charlottesville, UVA, Monticello, Ashlawn Highland, the James River, Richmond, Mt. Ida and award winning winery's and breweries. 8 people max staying in house

4.91 out of 5 average rating, 223 reviews

Popular amenities for Woodridge vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great vacation rentals in Woodridge

Guest favourite
A whimsical logo features a pink outline of a cottage, complete with a sloped roof and large front windows, evoking a charming and inviting atmosphere. The text 'Pink Cottage @ Locust Grange' is displayed prominently, emphasizing the location in Charlottesville, Virginia.
Cottage in Charlottesville

pink cottage @ locust grange

4.93 out of 5 average rating, 229 reviews
Top guest favourite
An aerial view captures a spacious guest house nestled among trees displaying vibrant autumn foliage. The surrounding landscape features a mix of green and colorful leaves, with an open area visible beside the property. Outdoor amenities are discernible, blending harmoniously with the natural setting.
Guest suite in Troy

Beaver Pond Farm - Near Charlottesville

5.0 out of 5 average rating, 235 reviews
Top guest favourite
Guest suite in Keswick

Cozy Wine Country Escape | Near Clifton Inn

5.0 out of 5 average rating, 127 reviews
Top guest favourite
The image features a charming two-story home surrounded by lush greenery and flowering trees. A circular driveway leads to the entrance, with manicured lawns enhancing the exterior. The backdrop includes rolling hills and bright blue skies, creating a serene and inviting setting.
Home in North Garden

Lux Country Retreat minutes from Charlottesville!

4.97 out of 5 average rating, 398 reviews
Guest favourite
The exterior of a charming cottage is featured, showcasing white brick walls and a sloped gray roof. Two dormer windows enhance the appearance, while a welcoming red door serves as a focal point. Well-maintained green grass and manicured shrubs surround the house, creating a friendly environment.
Cottage in Charlottesville

Adorable cottage steps from Grounds

4.91 out of 5 average rating, 458 reviews
Top guest favourite
A charming blue house is set on a green lot, framed by trees and bushes. The exterior features a welcoming front porch with steps leading up, and a gravel driveway accommodates multiple vehicles. Bright sunlight highlights the tidy, clean environment.
Bungalow in Scottsville

Scottsville Downtown Bungalow

4.98 out of 5 average rating, 223 reviews
Top guest favourite
A single-story home with light blue siding is set against a clear sky. A vibrant door adds a pop of color to the entrance, which is framed by landscaped flower beds. A paved walkway leads up from the driveway, inviting visitors towards the front entrance.
Home in Charlottesville

3BR / Pets Welcome / Fenced Yard / Fiber Internet

4.98 out of 5 average rating, 156 reviews
Guest favourite
A spacious two-story home is set against a backdrop of trees, showcasing a welcoming front entrance with a red door. The exterior features a combination of light siding and dark shutters, with flags displayed on either side of the entrance. A gravel driveway leads up to the house.
Home in Palmyra

Hot Tub | Fire Pit | Near Wineries | Kid-Friendly

4.93 out of 5 average rating, 87 reviews

Destinations to explore