Wintergreen Resort vacation rentals

5 out of 5 average rating, 119 reviews

A charming cottage is framed by lush green lawns, with two prominent stone chimneys rising from its exterior. The landscape is complemented by mature trees and distant mountains under a bright blue sky, creating a serene rural atmosphere.

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.

4.96 out of 5 average rating, 108 reviews

Bear's Mountain Escape

Dog friendly, 3 BR, 2 BA, loft style condo located in the heart of the Wintergreen Resort. Ski check-in, restaurants, the mountaintop market, & The Mountain Inn are all right across the street! 2-story unit with a main floor primary BR & hall bath. Main floor bonus room with single & trundle. The loft contains 2 twin beds and the 2nd full bath. Parking, pool, washer/dryer, and Wi-Fi included. Fully stocked kitchen, wood burning fireplace, balcony, all towels/linens provided. Sleeps up to six.

4.94 out of 5 average rating, 109 reviews

Cabin in Faber

Modern Cabin; River! 13 acres! Hiking! Wineries!

Beautiful cabin -13 acre wooded hillside along Rockfish River. Home provides a wonderful blend of modern comfort (high speed internet, updated kitchen) in a rustic exposed post and beam cabin; 3 floors of living spaces allow options for gathering, working, playing together but also apart. Sliding glass doors lead to a large wrap around porch with gas grill, dining table, plenty of seating and a tree level view of the natural setting and wildlife. So much to explore on the property and nearby!

Two chairs are positioned near a large panoramic window, offering expansive views of the Blue Ridge Mountains. A small table sits between the chairs, adding a touch of convenience to the inviting corner. Soft light filters through the sheer window treatments.

4.97 out of 5 average rating, 119 reviews

2 bdrm/2 full bath Best Views of Blue Ridge Mtns.

Best View of the Blue Ridge Mountains! Panoramic window views from the great room, dining area and kitchen. If you want to get a closer look step out on the observation deck to see the beautiful mountains and ski slopes (seasonal). Patio furniture is on the deck to enjoy morning sunrises and evening sunsets. All new stainless steel appliances in kitchen, Freshly painted throughout. 2 bedroom 2 bath Lots of activities to do at the Wintergreen Resort all year long. Year round resort activities.

4.86 out of 5 average rating, 107 reviews

Hot Tub Pool Table Dog OK Tennis Golf Shuffleboard

Sweeping views year round. Retreats, romantic weekends or adventurous getaways. Close to wineries, breweries, farmers market, and walking distance to three great hiking trails. Sleeps 16: K, K, Q, 2 DBL,4 twin, 1PO ★Dogs OK ★2,714sqft ★HOT TUB for 7 ★Sound system ★2-Story vaulted ceiling, gas fireplace, 60"TV ★Dining table for 6 + breakfast bar ★Workspace w/ FAST Wi-Fi ★Shuffleboard ★Pool table Seasonal pool/tennis. Resort access not included. Pet fee $150. 8min walk or 3min drive to ski.

The kitchen showcases a blend of rustic and modern design, featuring a farmhouse sink under large windows that invite natural light. A dark refrigerator is positioned adjacent to the sink, with wood accents enhancing the inviting atmosphere. Copper pendant lights provide additional warm illumination.

4.88 out of 5 average rating, 163 reviews

Wander Lodge: Golf, Spa, Wine, or just a getaway

Comfortable 3-BR, 2-bath condo on Devil's Knob Golf Course. Comfortably sleeps 6-7, 2 Queen beds, 1 full bed, futon, & comfy couch. Woodburning fireplace; balcony, small newly renovated kitchen w/stove, dishwasher, microwave, Keurig, tea kettle,coffee maker, crockpot; Smart TV w/ Streaming apps(free only); Walking distance to hiking trails, nature center, DeVine Wine & Coffee shop, tennis facilities, & the lovely wintergreen spa; less than 1 mile from Mountain Inn & restaurants & shops.

4.97 out of 5 average rating, 203 reviews

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 spacious outdoor deck features a round dining table surrounded by tall chairs, complemented by a striped couch with soft cushions. An umbrella provides shade, while the scenic mountain views extend into the distance, above a layer of mist.

4.94 out of 5 average rating, 133 reviews

BlueRidge Getaway- Dog Friendly

Relax and enjoy spectacular top-floor mountain views from the deck. This recently renovated unit is at the top of the mountain close to many hiking trails. Visit the Wintergreen village, with its restaurants and shops, with a 5 minute drive or an easy hike through the woods. You also have access to Rhodes Farm and Chestnut Hills pool. This condo is convenient to Devils Backbone, Bold Rock, and the litany of other breweries, cideries, distilleries, and restaurants. Dogs welcome!

A clean, inviting swimming pool is surrounded by lush greenery and tall trees. Comfortable lounge chairs are positioned nearby, and sunlight reflects off the water, creating a serene atmosphere. The pool area is enclosed with a wooden railing for safety.

4.98 out of 5 average rating, 137 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

4.88 out of 5 average rating, 194 reviews

A hot tub is positioned in the foreground, showcasing bubbling water. In the background, a vibrant pink tree stands against a clear blue sky, surrounded by green grass and blooming shrubs. String lights are suspended above, enhancing the outdoor space.

Barn in North Garden

Barn Suite, Mountain View's & Hot tub! Pets OK

Beautiful views just off Route 29, only 10 minutes from UVA, and tucked near the area’s finest wineries and top attractions. This intimate, luxury barn suite offers a private setting with 1 king bedroom, 1 bathroom, and an open-concept living room and kitchen featuring a cozy fireplace, queen pullout sofa bed, and single cot for extra guests. Unwind and relax on the back patio with breathtaking sunsets, hot tub, grill and a firepit — all fully yours to enjoy during your stay.

4.98 out of 5 average rating, 191 reviews

A spacious deck area is furnished with comfortable red seating, including two armchairs and a coffee table. Panoramic mountain views are visible in the distance, showcasing a blend of green and autumnal hues under a clear blue sky.

Apartment in Rockfish

Blue Ridge Bliss - For family & friends to enjoy!

Welcome to Blue Ridge Bliss! Come enjoy the mesmerizing mountain top views of this well-appointed condo in The Ledges of Wintergreen Resort. It’s the perfect place to unwind, unplug and recharge. Whether here to ski, hike, or visit Virginia wineries, cideries, or craft breweries you’re sure to enjoy the beautiful views from the living room and deck. A short walk to The Highlands lift and across the street from the dog park, and picnic area it’s an ideal location.

Townhouse in Wintergreen Resort

4.94 out of 5 average rating, 182 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!

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Apartments

Convenient locations with everyday essentials

Popular amenities for Wintergreen Resort vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Wintergreen Resort's top sights

The Nature Foundation at Wintergreen16 locals recommend

Ravens Roost Overlook22 locals recommend

Upper Shamokin Falls Trail31 locals recommend

Devil’s Knob Grill5 locals recommend

Wintergarden Pool & Spa6 locals recommend

Shamokin Springs Nature Preserve11 locals recommend

Wintergreen Resort house rentals

A welcoming living area features two leather couches arranged around a wooden coffee table, which is complemented by a patterned rug. Large windows allow natural light to illuminate the space, offering views of the surrounding trees. Sliding glass doors provide access to an outdoor deck.

5 out of 5 average rating, 105 reviews

Cozy Chalet | King Beds | Fireplace | Hot Tub

4.97 out of 5 average rating, 137 reviews

An inviting porch view overlooks a spacious green lawn bordered by trees. Soft sunlight filters through the branches, casting gentle shadows on the ground. Two planters with flowers add a touch of color to the scene, contributing to the tranquil outdoor atmosphere.

Home in Nellysford

“Small" House/Peaceful/Breweries/Hikes/Wineries

4.93 out of 5 average rating, 150 reviews

A gravel driveway leads towards a charming home framed by lush greenery and mountain views. Soft clouds drift across a blue sky, while manicured lawns and landscaping create a welcoming entrance.

Home in Lovingston

Three Springs with EV charging station

4.96 out of 5 average rating, 242 reviews

A living room is presented with a large, brown leather sofa in the foreground. An angular coffee table occupies the center, surrounded by two patterned armchairs. A television is positioned on a dark wood media console against a wall, with a potted plant adding a touch of greenery near a window dressed with light curtains.

Home in Afton

CritzerHouse - on 151- Walk to the Brewery!

4.88 out of 5 average rating, 142 reviews

A mountain house is surrounded by trees showcasing autumn foliage. Several porches are visible on the structure, enhancing its connection with nature. A gravel driveway leads up to the home, which is partially obscured by colorful leaves scattered on the ground.

Home in Roseland

Hikers, Spring has sprung & ready for you to come!

4.98 out of 5 average rating, 123 reviews

The exterior of the two-story house is illuminated at dusk, showcasing a welcoming aesthetic. A circular stone fire pit is situated in the foreground, surrounded by landscaped gravel and rocks. A pair of chairs sits nearby, inviting relaxation by the fire.

Home in Afton

Afton Home on 25 Acre Ridgetop with Amazing Views

4.94 out of 5 average rating, 108 reviews

A spacious deck features a hot tub and a dining area set for six. Scenic views of a vibrant sunset and surrounding landscape create a calming atmosphere, while the wooden decking enhances the connection to nature.

Home in Afton

Sycamore Shade: 151 House, HOT TUB, Mountain Views

4.88 out of 5 average rating, 343 reviews

A winding gravel driveway leads to a spacious home, surrounded by a lush green lawn. A large tree provides shade next to the house, which features a covered front porch. The setting includes open fields and a sky filled with soft clouds.

Home in Stuarts Draft

Blackwood Air B & B

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Ski-in/ski-out vacation rentals in Wintergreen Resort

A cozy living area features a teal sofa with a yellow accent pillow and a light wood coffee table. The kitchen is adjacent, showcasing modern appliances. Stairs lead to the loft bedroom. Artwork hangs on the wall, and natural light enters through high windows.

4.97 out of 5 average rating, 129 reviews

Mtn/Firework Views from Private Deck ~ King Suite

A panoramic view of rolling mountains under a dramatic sky filled with clouds. Light filters through the clouds, illuminating sections of the landscape. Tree-covered hills stretch into the distance, showcasing varying shades of green and blue.

4.72 out of 5 average rating, 141 reviews

Mountain Views

Chalet in Wintergreen Resort

The main living area features a local stone fireplace framed by large windows that allow natural light to fill the space. A comfortable couch and wooden coffee table create a welcoming atmosphere, complemented by decorative pillows and a small potted plant on the table.

4.91 out of 5 average rating, 104 reviews

Brown Bear Lodge, walk to the slopes!

5 out of 5 average rating, 904 reviews

A serene landscape showcases rolling hills adorned with autumn foliage. In the foreground, tall grass and scattered trees lead to a cozy house perched on a hillside, surrounded by vibrant fall colors. The distant mountains create a peaceful backdrop.

Yurt in Afton

Luxe Yurt w/Hot Tub in the Heart of the Blue Ridge

The hallway is lined with unique striped wooden flooring, leading to cozy living spaces. A small table with a lamp and decorative artwork adds warmth. In the distance, a living area features a fireplace and a TV, with natural light coming through the windows.

5 out of 5 average rating, 13 reviews

Ski- In/Ski-Out Comfy Condo

A balcony view captures rolling green hills beneath a layer of clouds, with distant mountain peaks rising above. A wrought iron dining set is present on the balcony, providing a serene space for enjoying the landscape.

4.96 out of 5 average rating, 178 reviews

Ski-in/Ski-out Wintergreen Highlands Condo -Views!

Cabin in Wintergreen Resort

A cabin exterior is showcased, featuring a deck with various chairs and a table for outdoor dining. Large windows reflect natural light, complementing the surrounding greenery. A stone feature is visible below the deck, adding organic texture to the scene.

4.99 out of 5 average rating, 134 reviews

Family Friendly Home with All Necessities Included

An open living area features a comfortable sofa with decorative pillows and a coffee table. A dining counter with tall stools is visible, alongside a well-equipped kitchen that includes a refrigerator and microwave. Wall art complements the muted tones of the room.

4.9 out of 5 average rating, 142 reviews

Cozy Comfort with a View - Wintergreen Resort

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Ski-in/ski-out houses in Wintergreen Resort

A modern kitchen features a large island with a granite countertop and seating for several guests. The cabinets are white with sleek hardware, and high-end appliances are visible. Large windows provide natural light and a view of the surrounding trees.

5 out of 5 average rating, 17 reviews

Wintergreen condo ski-in/ski-out

A cozy living room is featured, showcasing a wooden ceiling and a fireplace. A deep blue sectional sofa is arranged around a coffee table. Natural light floods in through a door leading to the balcony, revealing views of the surrounding trees and winter landscape.

5 out of 5 average rating, 17 reviews

Premiere 2 BR Getaway Ski In/Out Wintergreen Condo

The living room features high ceilings with exposed beams and large windows showcasing the surrounding trees. A light gray sofa and armchairs provide comfortable seating, while a round coffee table sits at the center. A jute area rug adds texture to the hardwood floor.

4.94 out of 5 average rating, 48 reviews

Treeloft 17: Ski in/ski out – EV charger – 3BR/3BA

The exterior of a modern mountain condo is showcased, featuring a wooden ramp leading to the entrance. The structure is framed by trees and includes triangular windows that complement the wood siding, creating a harmonious blend with the natural surroundings.

4.93 out of 5 average rating, 58 reviews

Wintergreen Condo~ 1 Minute To Four Seasons Resort

A Great Room is presented, featuring two dark leather sofas and a wooden coffee table at its center. Large windows offer views of the surrounding trees, while a mounted television and a lamp complete the space. A vibrant area rug adds color to the wooden floor.

4.69 out of 5 average rating, 61 reviews

Cliff Hanger Hot Tub Dogs OK Pool Tennis Golf Hike

4.67 out of 5 average rating, 3 reviews

The Distinguished Squirrel Chalet walking distance

An inviting outdoor space features a hot tub, a gas fire pit, and comfortable seating arrangements. The area is designed for relaxation, showcasing smooth wooden decking and views of the surrounding trees. Sliding glass doors provide access to the interior of the home.

5 out of 5 average rating, 59 reviews

Luxe Modern Retreat: Steps to Ski & Hike! Views!

A bubbling hot tub is positioned on the deck, with water being jetted out. Trees with sparse branches surround the area, reflecting the winter season. Clear skies are visible, contributing to a serene outdoor atmosphere.