Holiday rentals with a patio in Wintergreen Resort

Holiday home in Lovingston

The cabin's exterior is surrounded by lush greenery, featuring a spacious porch with seating and a hot tub nearby. The two-story structure is constructed of wood, with large windows allowing natural light to fill the interior. A picnic table is located in the yard.

4.96 out of 5 average rating, 223 reviews

Ultimate cabin in the mountains

This unique and secluded cabin sits on 75 acres in the Blue Ridge mountains. Enjoy the cozy wood fireplace, hot tub, charcoal grill, and fast, reliable fiberoptic internet if you need to get some work done while you're away. It has a washer and dryer, a full kitchen, and is pet-friendly (no pet fee!), so you can enjoy it with the whole family. There is a 4K 55” smart TV with apps, a Tesla LVL 2 charger, a cabinet full of board games, books, and plenty of items to entertain both kids and adults!

5 out of 5 average rating, 207 reviews

A cozy cottage, named the 'Sugah Shack,' is nestled amidst the rolling hills of the Blue Ridge Mountains. The white exterior contrasts with the vibrant greenery surrounding the property, while the majestic mountains form a picturesque backdrop against a bright, partly cloudy sky.

Cottage in Afton

Cozy Mountain Cottage on Brew/Wine Trail-King Bed

Welcome to the Sugah Shack, a cozy, beautifully appointed new construction cottage nestled in the foothills of the Blue Ridge Mountains! Located midway on the Brew Ridge Trail, but 500 yards off the byway, so guests have a quiet retreat. Perfect for romantic getaways, destination telework space, or families exploring this outdoor paradise community. Stunning property boasts beautiful vistas with sweeping 300-degree mountain and a year-round calendar of outdoor activities. GAS FIREPLACE/FIREPIT

A cozy living area features natural stone accents around a wood-burning fireplace. A small dining table with two chairs is positioned near large windows, allowing ample natural light. Green accent walls enhance the inviting atmosphere, while a comfortable seating area is visible nearby.

4.91 out of 5 average rating, 191 reviews

Tips Up: Cozy Slopeside Retreat w/ Fireplace

The mountains are calling and you must go. Well, you don't have to, but we think it's a good idea. Make Tips Up your home while you're away. With slopeside views, a cozy and comfortable ambiance, and close proximity to skiing (only 100 yards from the slopes!) and hiking, this 1B/1BA condo is the perfect getaway for outdoor enthusiasts seeking a mountain escape. Relax at nearby breweries and wineries with unbeatable views, and return to your condo to enjoy the amenities of Wintergreen Resort.

5 out of 5 average rating, 143 reviews

A charming cottage is nestled among lush green grass and surrounded by trees. Its metal roof and white siding are complemented by well-maintained shrubbery. Dappled sunlight filters through the tree branches, creating a serene outdoor ambiance.

Cottage in Covesville

Historic cottage with stunning mountain views

Welcome to Rose Cottage in picturesque Albemarle County, where you'll enjoy expansive 360-degree views of the mountains surrounding historic Cove Lawn Farm. Relax in the tranquil rural setting or stroll more than two miles of comfortable walking paths that wind through 25 acres of stream-lined hayfields. From Rose Cottage, you're just minutes from the best local cideries, distilleries, and wineries including Pippin Hill Farm & Vineyards. Easy 20-minute drive to UVa and 22 minutes to Monticello.

5 out of 5 average rating, 100 reviews

A newly constructed cottage is set on a private mountain lot, featuring a light-colored exterior and a sloped roof. A spacious screened porch with wooden steps is visible, surrounded by green grass and trees. Natural landscaping enhances the peaceful environment.

Cabin in Roseland

Mountain Hideaway Cottage

Perfect for couples or families. Tucked away on its own private mountain acreage with stream access. Large screened porch for talking into the night or enjoying your morning coffee. Ask about same day after 5pm discount! Less than 2 miles to Devil's Backbone and Bold Rock. Minutes to Blue Ridge Parkway,Appalachian Trail, Wintergreen, breweries, wineries, cideries, restaurants, horseback riding, hiking, mountain lakes, & antique shopping. Gas fireplace. 1G WiFi & SMART TV. Fire pit and wood.

A spacious living area features a wood-burning fireplace surrounded by light-colored walls. A comfortable couch, adorned with a welcoming throw pillow, faces a wooden coffee table. Natural light enters through large windows, offering views of the outdoor greenery.

4.93 out of 5 average rating, 238 reviews

The Modern Mountain Condo

Conveniently located within the 4-season Wintergreen Resort, this recently renovated condo offers a quiet and cozy stay while you take in the mountain views and enjoy endless outdoor activities, wineries, breweries, restaurants, and antique shops. Rest and recharge while you enjoy the light-filled, open floor plan with a wood-burning fireplace, a kitchen with plenty of cabinet space, and full-sized appliances for cooking. Private patio and community pool access are located outside the unit.

4.99 out of 5 average rating, 218 reviews

A charming bungalow exterior is showcased, featuring a wraparound porch with seating. Surrounding greenery, including bushes and grass, enhances the outdoor appeal. The structure is painted in a dark hue with wooden accents, complementing the clear blue sky.

Bungalow in Afton

The Bungalow at Afton Mountain Retreat by Veritas

Welcome to The Bungalow at Afton Mountain Retreat in the heart of Brewery Trail/Route 151, Vineyard country and the foothills of the Blue Ridge Mountains. The Bungalow is located 1/4th mile from Veritas Vineyard. It is within 10 minutes to every brewery, vineyard, distillery and cidery along Route 151 Crozet, 1 mile from the newly opened Blue Ridge Tunnel and 20 minutes to Wintergreen Resort for winter fun! Completely remodeled and ready to spoil the best guests who simply want to unwind.

A spacious living area features a stone fireplace as the focal point, framed by large windows that offer views of the surrounding trees. A comfortable sectional sofa is arranged around a coffee table, with a television positioned on a media console to the side.

4.96 out of 5 average rating, 103 reviews

Cozy 5-bedroom home for large gatherings.

Within the Wintergreen Resort, this 4-season mountain home is perfect for a large gathering with friends and family. A generously stocked home for all your needs and occasions. A clean, comfortable, and relaxing home with many amenities and accessible to many outdoor adventures. Wintergreen Resort provides a great skiing experience. Being near the scenic Blue Ridge Parkway, Skyline Drive and the Appalachian Trail, you will wish to return every season to get away from your busy schedules.

4.96 out of 5 average rating, 218 reviews

A two-story cabin features a light-colored exterior with a steep roof and large windows. A wraparound deck includes wooden railings draped with soft outdoor lighting. A walkway leads from the deck to the landscaped area, surrounded by lush greenery.

Cabin in Afton

Inn at the Woods: Updated Cabin w/Mountain Views

Fall in love with the charm of this recently updated ‘Hansel & Gretel’ style cabin located on Castle Rock Mountain. This cabin has 3 bedrooms + a loft, with a total of 4 queen beds. Hike and explore the 20+ acres or relax on the large multi-tiered deck and fire-pit area while soaking in the mountain sunsets. Enjoy nearby dining, breweries, or wineries, the historical town of Charlottesville, or spa, golf, tennis, and skiing at the Wintergreen Resort - both just a short drive away.

A private balcony features wooden railings, with a light dusting of snow on the ledge. Lush pine trees stand prominently in the background, contrasting against a clear blue sky and hints of distant landscape, contributing to a serene outdoor viewing experience.

4.97 out of 5 average rating, 152 reviews

2-min drive from slopes, stair-free/free firewood!

Peaceful, recently renovated mountain-top retreat. Relax or work from home. End your day with a hike or spa treatment around the corner—linger with a glass of wine at sunset. It’s all only a 2 minute walk from the front door. Welcome to our mountain home! 2-3 min drive from ski lifts/resort, hiking Free firewood (seasonal) Family games & smart TVs (no cable) for movie night (must sign into your own subscriptions) Smartlock entry Stair-free entry *outdoor HOA pools CLOSEDe

A private furnished patio features a cozy seating area with light-colored cushions on a dark frame sofa. A wooden coffee table sits in front, accented by a woven rug. The surrounding greenery adds a natural backdrop, creating a peaceful setting for relaxation.

4.96 out of 5 average rating, 161 reviews

1 bedroom condo, hiking, breweries, wineries

Enjoy the mountains in the spring & summer enjoy hiking or a swim in the heapool! 1BR 1BA centrally located in Wintergreen 5 minute walk to Wintergreen resort Close to many hiking trails Enjoy the many breweries & wineries in the area Mountaintop Market is across the street 1 Bedroom 1 Bath & New queen sleeper sofa Stocked kitchen, cookware, spices & cooking oils Premium coffee & assorted tea Private furnished patio Wood burning fireplace, all you need for a quiet getaway

4.99 out of 5 average rating, 274 reviews

A charming cottage is positioned alongside a gently flowing trout stream, with a backdrop of lush greenery. Rocks line the water's edge, and a large, fenced yard surrounds the home, providing a peaceful setting. A red roof contrasts beautifully with the natural surroundings.

Cottage in Tyro

Bear Creek Inn

You will be renting the 3 bedroom cottage, very large, fenced yard for your pet. Relax at this quiet, peaceful place with year round trout stream. Minutes from the breweries and wineries on Nelson 151. Plenty of outdoor activities to enjoy. The George Washington National Forest is across the street for exploring, hiking and hunting. The house is only 4 miles from Crabtree Falls and several minutes from the Appalachian Trail access. Wintergreen Resort is 12 miles away.

Popular amenities for rentals with patio in Wintergreen Resort

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Flat rentals with a patio

A welcoming entryway is presented with floral wallpaper and green wainscoting. A small armchair, paired with a decorative lamp and side table, creates a cozy reading nook. Artwork is hung on the walls, and a door leading to the outside is visible at the end of the hallway.

5 out of 5 average rating, 166 reviews

Queen City Hideaway

4.93 out of 5 average rating, 106 reviews

A spacious living area is illuminated by natural light, featuring a modern sectional couch in blue. The room showcases exposed wooden beams along the ceiling and a round area rug with intricate patterns. A small coffee table and vibrant accent pillows add inviting touches.

Flat in Charlottesville

Beautiful, Cozy, Downtown Apt!

Flat in Wintergreen Resort

An outdoor dining setup on a spacious deck features several plates with a breakfast spread, including eggs, fruit, and pastries. A steaming cup and a glass of juice are present. In the background, a telescope is positioned to enjoy the scenic mountain view under a cloudy sky.

4.97 out of 5 average rating, 37 reviews

Luxury Condo: Stunning Slope Views, Sauna, Dogs-Ok

The exterior of the building displays a two-story structure with light brown siding and a front porch adorned with white railings. Windows are visible on both levels, complemented by a small garden and walkway leading up to the entrance.

4.93 out of 5 average rating, 141 reviews

Walker's dream. Close to downtown.

A comfortable living area is furnished with a dark sofa adorned with textured cushions. Two light-colored armchairs are positioned nearby, and a small side table holds a plant. Natural light floods the space through large windows, illuminating the patterned area rug.

4.93 out of 5 average rating, 205 reviews

Traveler’s Escape-1 bedroom. Walk to downtown!

Superhost

A cozy living area is presented with a beige sectional sofa and an armchair. A 60" Roku TV is mounted on the wall. Shelves hold various decorative items. A large clock complements the light-colored textured walls, while a framed scenic photograph adds a subtle touch of nature.

Flat in Buena Vista

4.84 out of 5 average rating, 323 reviews

Rustic Basement Unit

Flat in Wintergreen Resort

A balcony is featured, showcasing two Adirondack-style chairs positioned for optimal mountain views. Sunrise illuminates the expansive horizon, with soft light reflecting off the distant landscapes. The floor is made of wood, enhancing the outdoor ambiance.

5 out of 5 average rating, 99 reviews

Endless Mountain Top Views from All The Way Up!

A vibrant sunset is captured over rolling hills, with shades of orange and pink filling the sky. A grassy field in the foreground leads to a white fence, and buildings are visible in the distance under a dramatic cloud formation.

4.99 out of 5 average rating, 137 reviews

Willow Ridge

House rentals with a patio

A spacious living area is highlighted by a soaring stone fireplace and large windows allowing natural light to filter in. Comfortable seating arrangements are present, complemented by vibrant artwork on the walls. A warm wooden floor adds a cozy touch to the inviting atmosphere.

4.93 out of 5 average rating, 27 reviews

Bluebird Mtn Home ~Dog Friendly ~ ~No step entry~

A deck area is shown, featuring comfortable seating arrangements and a coffee table. Lush greenery surrounds the space, with expansive views of the distant Blue Ridge Mountains under a clear blue sky, creating a serene outdoor retreat.

4.91 out of 5 average rating, 32 reviews

Wren Time

4.96 out of 5 average rating, 109 reviews

The exterior of a modern farmhouse is showcased, featuring large windows that reflect the surrounding trees. A spacious patio is seen, with a set of outdoor chairs. The house's white siding contrasts with the green landscape and blue sky, creating an inviting atmosphere.

Home in Afton

Hilltop at Mountain View Meadow

4.98 out of 5 average rating, 134 reviews

The exterior view showcases a modern blue house set against a backdrop of lush green hills. A wooden deck extends from the home, providing access to outdoor space. The gravel driveway is lined with a rustic split-rail fence, enhancing the natural feel of the surroundings.

Home in Nellysford

Llama Loft | Fire Pit | Fenced Yard | Nelson 151

A spacious house is set amidst a serene winter landscape, surrounded by trees and blanketed in snow. The wooden deck extends around the house, offering ample outdoor space. Large windows allow for natural light, enhancing the connection with the surrounding nature.

4.92 out of 5 average rating, 65 reviews

4 min to Ski: Whispering Creek Hot Tub King Beds

Superhost

A cozy living area is highlighted by a wood-burning stove with a green brick surround. An inviting sectional sofa is positioned around a coffee table, while a mounted television above the fireplace allows for entertainment. Natural light filters through multiple windows adorned with white shutters.

Home in Waynesboro

4.77 out of 5 average rating, 150 reviews

Hot Tub - Fire Pit - Game Room

4.93 out of 5 average rating, 127 reviews

An outdoor fire pit area is surrounded by gray Adirondack chairs, set on a gravel base, with a scenic view of the mountains in the background. A spacious lawn features trees and flowering plants, creating an inviting space for relaxation and gatherings.

Home in Afton

Farmhouse on 151 w/ Firepit, Huge Yard, Mtn Views!

4.99 out of 5 average rating, 133 reviews

A three-story wooden house is nestled among lush greenery in a forested setting. The deck and patio area are accessible, surrounded by trees and natural landscaping, creating a serene environment for relaxation.

Home in Nellysford

Cabin in Woods | Family & Dog Friendly | Fire Pit

Apartment rentals with a patio

A comfortable living room features a cozy couch adorned with throw pillows, situated near a sleek fireplace. A round, woven coffee table stands in the center, while minimalist wall art and a reflective mirror enhance the clean, modern aesthetic.

5 out of 5 average rating, 20 reviews

Retreat @ 3 Ridges | 8 min to Blue Ridge Parkway

A spacious living area features large windows that provide expansive views of the surrounding landscape. Comfortable seating includes a sectional couch and a reclining chair, arranged around a wooden coffee table. A sleek stone fireplace and a mounted television add to the contemporary decor.

4.94 out of 5 average rating, 32 reviews

Wintergreen Mountain Views - Diamond in the Slopes

A balcony view reveals a vast expanse of rolling green mountains under a clear blue sky. A square table is surrounded by two woven chairs, inviting guests to enjoy the serene landscape of the Blue Ridge Mountains and Rockfish Valley.

4.92 out of 5 average rating, 13 reviews

Condo with Valley Views!

An outdoor deck features a comfortable seating area with plush cushions and a coffee table. Two glasses of wine rest atop the table, surrounded by panoramic views of the Blue Ridge Mountains bathed in soft hues of sunset.

5 out of 5 average rating, 46 reviews

Buena Vista Panoramic Retreat: Million Dollar View

The living area features a large sectional sofa facing a stone fireplace, with a wooden accent wall above. Floor-to-ceiling windows provide expansive views of the surrounding forest and mountains. A dining table and four chairs sit nearby, with stylish decor enhancing the inviting atmosphere.

5 out of 5 average rating, 34 reviews

Lovely Ski Front Private 3-bed/3-bath condo

A cozy living area features a stone fireplace with a wooden mantle. Natural light enters through large windows framed by light curtains. Comfortable seating includes a brown sofa with decorative pillows and a stylish orange chair. An adjacent dining table offers space for meals.

5 out of 5 average rating, 15 reviews

3 Ridges 3 min walk to slopes,besides inn,King bed

A sunset view is captured over the mountains, with the sun dipping below the horizon, casting warm hues across the sky. Dense trees frame the scene, providing a sense of tranquility amid the natural landscape.

4.94 out of 5 average rating, 36 reviews

Love of mountains oh fill my cup

A cozy living area is presented, featuring large windows allowing natural light to fill the space. A sleek fireplace is surrounded by a dark stone facade. A flat-screen TV is mounted above, while a coffee table and patterned rug add to the inviting atmosphere.