Holiday rentals in Cunningham

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Top-rated holiday rentals in Cunningham

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Top guest favourite

A light-filled living room features a comfortable sofa adorned with decorative cushions. A coffee table sits in front, and two lamps illuminate the space. Large windows overlook the backyard, allowing natural light to enhance the inviting atmosphere.

Cottage in Palmyra

Bluebird Cottage B: Quiet, Firepit, Patio, Games

You’ll enjoy the simple charms of this home for up to 4 guests conveniently located near Lake Monticello, Charlottesville, the Rivanna River, and wineries. Relax in peace in a quiet neighborhood. Enjoy your private patio with outdoor dining table. Play board games, cornhole, and horseshoes. Make memories around the firepit. You’ll have everything you need, including fully equipped kitchen, washer-dryer, electric fireplace, fast Wi-Fi, 2 smart TVs for streaming services w/antenna for local fare.

LocationFamilyShared spaces

4.95 out of 5 average rating, 180 reviews

Guest favourite

A cozy living area is shown featuring a dark brown sofa with a soft yellow throw blanket. Wall shelves display books and a TV is mounted nearby. Two sets of glass doors lead to an outdoor space, allowing natural light to brighten the beige walls.

Guest suite in Palmyra

Guest Suite by Wineries/Orchards/Cville/Monticello

Welcome to Deer Hideout Retreat! We are located in Palmyra, Virginia, on two acres of land. There's an abundance to see and to do around here, and we hope you choose our home for your stay. We are far enough outside of the city to enjoy the peace and quiet, but just a short drive to all the action. We are close to Monticello, James Monroe's Highland and 28 minutes away from the city center of historic Charlottesville. There are plenty of vineyards all around us and a couple of orchards, too.

ValueLocationHiking

4.99 out of 5 average rating, 120 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.

Flat 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.

LocationFamilyQuiet

4.99 out of 5 average rating, 143 reviews

Top guest favourite

The exterior of the converted barn and silo is softly illuminated by string lights at dusk. A serene pond, framed by smooth stones, reflects the warm glow of light. The porch invites relaxation with its spacious seating and rustic charm, creating a peaceful outdoor setting.

Barn in Louisa

Unique OASIS - Silo Barn - Swim Pond- 5 Miles Trai

4 unique rentals available (click our profile)! Unwind at this Central VA Country Paradise! Stay in a converted Barn & Silo w/ private natural swim pond and waterfall tucked into the woods on 140 Acres! Your own Oasis awaits, step out on your porch for coffee/drinks with the farm animals. Take a hike around the Lake on the 5+ miles of trails before cooling off in the pond while you gaze up at the stars. Sheep, Dwarf Fainting goats(next to silo 10' away), Chickens, Ducks, Bunnies, & Turkeys.

FamilyValueSleep quality

4.99 out of 5 average rating, 148 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.

LocationValueBiking

4.99 out of 5 average rating, 139 reviews

Top guest favourite

The treehouse structure is framed by lush greenery, featuring a combination of wood and metal elements. A spacious deck surrounds the entrance, leading to steps that connect to the ground. Large windows offer views of the forest, enhancing the connection to nature.

Treehouse in Palmyra

Delightful one bedroom treehouse with king bed

You'll love this unique and romantic escape. Come and disconnect from the world and reconnect with each other in the Treehouse at Backabit Farm. You can enjoy the indoor fireplace or outside propane fire pit! Private deck for gazing at the stars or watching the wildlife. Two person hammock tucked under the trees! Inside you will find king bed with a view out of the three large windows, loveseat, tv, microwave, small fridge, coffee station and quaint bathroom with tiled shower.

LocationValueNearby

4.97 out of 5 average rating, 205 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

Relax at this unique and tranquil getaway. Sit on the screened in porch and enjoy the sights and sounds of nature while you enjoy a beverage. Visit the Downtown Mall, Monticello, a Winery, a Brewery, or UVA (20 min). Enjoy a dip in the pool (JUN-AUG) or relax by the firepit - perhaps joined by a Great Pyrenees for cocktails. Feel like staying in - SmartTVs with YouTubeTV (which includes local channels) and Gig-speed Internet await. Easy checkout. No cleaning fee.

FamilyValueWalkability

5.0 out of 5 average rating, 237 reviews

Top guest favourite

Treehouse in Stanardsville

CloudPointe Retreat

Rare Appalachian Treehouse Gem! Luxurious, one-of-a-kind retreat for couples. Elevated tiny house among the treetops, private parking, plush bedroom, sleek bathroom, beautiful kitchenette, loveseat, lounge, private double-level decks, fireside lounging (wood provided), gas grill, and patio with a hot tub! Surrounded by nature, with wineries, hikes, restaurants and shopping all nearby. Please come and relax and revel in the beauty of nature! 4WD is highly recommended.

FamilyLocationAmenities

4.98 out of 5 average rating, 135 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 home 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.

LocationValuePets

4.93 out of 5 average rating, 295 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!

FamilyValueSleep quality

4.97 out of 5 average rating, 183 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.

FamilyLocationParking

4.97 out of 5 average rating, 142 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

ValueFamilyAmenities

4.91 out of 5 average rating, 225 reviews