Vacation rentals with a patio in Wintergreen Resort

Vacation 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, 220 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, 189 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, 142 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.

4.97 out of 5 average rating, 141 reviews

A rustic log cabin is featured with a green metal roof. An outdoor fire pit surrounded by stones provides a warm glow in front of the cabin. Comfortable chairs are positioned nearby, inviting relaxation. A gas grill is seen to the side, enhancing the outdoor experience.

Cabin in Lyndhurst

Cozy Log Cabin

Relax and unwind in this secluded, hand-hewn log cabin with all the modern conveniences. 10 minutes off the Blue Ridge Parkway from mile marker 16, minutes from Shenandoah National Park and the Appalachian Trail, close to 4 breweries, 6 wineries, 3 cideries, and Wintergreen Four-Season Resort. Located on over 300 acres of private land with plenty of room to explore and enjoy the wildlife. Come witness the brilliant night sky lying in an open field with no city lights to diminish the experience.

4.99 out of 5 average rating, 131 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

Welcome to the Wooder House, a cozy haven nestled in the woods of Virginia's beautiful Nelson County! Enjoy relaxing and connecting in a private home centered on 38 wooded acres, but close to NelCo fun! - Peaceful nature retreat - Outdoor patio & fire pit - Great for families & dogs - Fully stocked kitchen - Private trail + hiking options nearby - 8+ min. to wineries, breweries, cideries, restaurants - 25 min. to Wintergreen Resort For more photos and fun, check us out on IG: @thewooderhouse

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, 237 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.

4.96 out of 5 average rating, 217 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, 151 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, 159 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

A living room features a stone fireplace with a wooden mantel. A clock is mounted above, and decorative items are displayed on the mantel. Hardwood flooring complements the room's layout. The space is open to a kitchen area, visible in the background, with light cabinets and appliances.

4.97 out of 5 average rating, 101 reviews

Wintergreen Resort King bed, Fire place, 2 Bd/2 Br

Forget your worries in this spacious and serene space. Condo has been completely renovated and can be enjoyed all year round! Located between the Wintergarden Spa, the Nature Foundation and the Devils Knob Sports Center (golf, tennis and fine dining restaurant) Stone Ridge neighborhood is centrally positioned to most of the Resort amenities. 5 min drive to slopes 5 mins to Market 15 to Devils Backbone 3 mins to Devils Knob golf course

Townhouse in Wintergreen Resort

The exterior of a two-story townhome is shown, featuring natural wood tones and a welcoming American flag displayed. A wooden ramp leads to the entrance, surrounded by wooded greenery, with large windows that allow for ample natural light.

4.94 out of 5 average rating, 196 reviews

Fantastic home in an ideal location, dogs welcome!

Wintergreen Resort is a fantastic, all season destination, with adventures for everyone! We are a pet and kid friendly, 2br/2ba townhome, located in the heart of all the action. Ski check-in, Mountain Inn, restaurants, & the Market stocked with all the essentials located right next to our community. Come hike, swim in our private pool or lakes, ski, snowboard, tube, and vineyard, brewery, distillery, or cider hop. We have it all!

Popular amenities for Wintergreen Resort patio rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment 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, 164 reviews

Queen City Hideaway

Apartment in Charlottesville

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.

4.93 out of 5 average rating, 103 reviews

Beautiful, Cozy, Downtown Apt!

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, 137 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, 204 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.

Apartment in Buena Vista

4.84 out of 5 average rating, 322 reviews

Rustic Basement Unit

Apartment 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!

Apartment in Wintergreen Resort

4.89 out of 5 average rating, 9 reviews

Eagles Court Ski In/Out Condo

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, 135 reviews

Willow Ridge

House rentals with a patio

Home in Wintergreen Resort

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.

4.9 out of 5 average rating, 31 reviews

Wren Time

4.93 out of 5 average rating, 29 reviews

A warm and inviting living space features a stone fireplace with a fire glowing inside. A comfortable chair with patterned fabric sits beside a small glass coffee table. Natural light enters through large windows, creating a cozy atmosphere.

Home in Roseland

Hot Tub! Wintergreen Resort!

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

Mountain View Meadow Hilltop

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

4.9 out of 5 average rating, 31 reviews

A charming house is positioned at the edge of a gravel road, surrounded by a grassy area with blooming flower beds. Lush trees line the road, complementing the serene landscape under a partly cloudy sky.

Home in Faber

Artist's Cottage, Appalachian Getaway, WIFI

Home in Wintergreen Resort

A two-story mountain home is surrounded by a wooded landscape, showcasing a large front deck supported by wooden beams. The exterior features light-colored siding and stone accents, with a gravel pathway leading to the entrance.

5 out of 5 average rating, 21 reviews

White Wolf Chalet at Wintergreen

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

4.78 out of 5 average rating, 149 reviews

Hot Tub - Fire Pit - Game Room

5 out of 5 average rating, 37 reviews

The open living area showcases a high ceiling with a fan and large windows that allow natural light to fill the space. A dining area features a round table surrounded by chairs, while comfortable seating is arranged near a wooden accent wall. A stylish archway leads to an organized kitchen.

Home in Roseland

Wintergreen Mountain Retreat

Condo 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, 31 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.

5 out of 5 average rating, 10 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, 45 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, 14 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, 35 reviews

Love of mountains oh fill my cup

A stunning view of rolling mountains illuminated by the soft glow of sunset. Layers of hills are visible, with trees blanketing the landscape. The sky displays a mix of orange and gray hues, enhancing the tranquil atmosphere of the scene.