Wintergreen vacation rentals

5 out of 5 average rating, 116 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.

4.89 out of 5 average rating, 186 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 off route 29, approximately 10 minutes to UVA, nestled near the area's BEST wineries and attractions. This barndominium has 1 bedroom, 1 bathroom, open living area with a pull-out sofa bed and cot for additional guests. Relax and enjoy the breathtaking scenery and sunsets outside on the patio complete with a hot tub, firepit, and lounge chairs. This cozy barn has all you need and more for a great quality stay. You can upgrade your space at anytime to include the downstairs suites

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, 101 reviews

A private porch is shown with wooden flooring and a rustic wooden ceiling. Several outdoor chairs are arranged around a small table. Trees are visible in the background, providing a natural setting.

Cabin in Crozet

#4 Cabin Near Wineries, Breweries, UVA, & Hiking

The #4 Loblolly Cottage is an eco-friendly cabin overlooking a lake. Small 450 sq ft, cottage has a queen size bed in the primary bedroom, bunk beds in the second bedroom and a full size futon in living room. Kitchenette equipped with modern appliances and breakfast table. Bathroom and shower. Wi-Fi. Private porch. Pets are welcome for an additional fee. Hike, canoe, fish and bike onsite on a 129 acres. Close by wineries, 15 min to Shenandoah National Park. This cabin is ideal for families!

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, 202 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, 132 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, 130 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

4.98 out of 5 average rating, 187 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.

4.91 out of 5 average rating, 264 reviews

A bright living room features modern furnishings, including a cozy gray sofa and a large yellow chair. Natural light fills the space through a window, while colorful artwork adorns the walls. A smart TV is positioned on a white console, adding to the inviting atmosphere.

Bungalow in Waynesboro

Cheerful 2 bd bungalow with HOT TUB! Pet friendly!

Enjoy the entire home to yourself, including a relaxing backyard retreat with hot tub. Perfect for singles or couples who want to stay home and relax or visit the sites then come home to enjoy the hot tub under the stars. 10 min drive to shopping; 10 min to Blue Ridge Parkway & Skyline Drive; 15 min to 151 Breweries. kayaking/canoeing/hiking/fishing on the beautiful South River.

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Popular amenities for Wintergreen vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Wintergreen's top sights

Bold Rock Hard Cider251 locals recommend

Basic Necessities103 locals recommend

Blue Ridge Pig58 locals recommend

Rockfish Valley Foundation Natural History Center27 locals recommend

Rockfish Valley Trail Parking Lot14 locals recommend

Wintergreen True Value Hardware7 locals recommend

Wintergreen house rentals

4.95 out of 5 average rating, 130 reviews

Home in Charlottesville

Scenic Private Farm House Great for Large Groups

4.93 out of 5 average rating, 150 reviews

A charming three-bedroom home is surrounded by lush gardens filled with colorful flowers and vibrant greenery. Towering hills rise in the background, while a variety of trees and shrubs add to the scenic landscape of the property.

Home in Lovingston

Three Springs with EV charging station

4.98 out of 5 average rating, 149 reviews

A newly constructed house presents a modern facade with blue siding and white trim. A covered porch offers seating, surrounded by manicured shrubbery and flowers. The driveway leads to a spacious garage, while lush green grass enhances the inviting exterior setting.

Home in Charlottesville

UVa, Stadium, Downtown , Wineries & The Corner

4.97 out of 5 average rating, 105 reviews

Home in Crozet

"The Shire" at Hollow View: Crozet Farmhouse

4.96 out of 5 average rating, 241 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!

4.91 out of 5 average rating, 137 reviews

Home in Staunton

Little Yellow House: Walk to Downtown Staunton

4.88 out of 5 average rating, 142 reviews

Home in Roseland

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

4.93 out of 5 average rating, 106 reviews

Home in Afton

Sycamore Shade: 151 House, HOT TUB, Mountain Views

Show all

Ski-in/ski-out vacation rentals in Wintergreen

4.97 out of 5 average rating, 126 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 soaring ceilings and a local stone fireplace as the focal point. Comfortable seating is arranged around a wooden coffee table. Large windows bring in natural light, and a smart TV is positioned to one side, enhancing the space's functionality.

4.91 out of 5 average rating, 103 reviews

Brown Bear Lodge, walk to the slopes!

5 out of 5 average rating, 900 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

Townhouse in Wintergreen Resort

The living area features a cozy red sofa and a wooden coffee table, complemented by a colorful area rug. A circular wooden dining table with four chairs sits nearby, illuminated by natural light from the large windows. A stone fireplace adds a rustic touch to the atmosphere.

4.94 out of 5 average rating, 180 reviews

Fantastic home in an ideal location, dogs welcome!

A well-furnished living room features a large sectional sofa alongside a cozy chair. A coffee table sits in the center, while a stone fireplace adds warmth. Glass doors provide access to a balcony with dining furniture, highlighting scenic mountain views.

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, 133 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

Show all

Ski-in/ski-out houses in Wintergreen

A spacious living area features a gray sectional sofa arranged around a rustic stone fireplace. A wooden shelf displays decorative items, and a rocking chair adds a cozy element. The open layout connects to a modern kitchen area with bar seating visible in the background.

5 out of 5 average rating, 16 reviews

Wintergreen condo ski-in/ski-out

5 out of 5 average rating, 15 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 image captures the exterior of a mountain condo, featuring a wooden ramp leading to the main entrance. The structure displays a combination of natural wood tones, triangular gable, and multiple windows. Lush green trees surround the condo, enhancing the sense of privacy.

4.93 out of 5 average rating, 58 reviews

Wintergreen Condo~ 1 Minute To Four Seasons Resort

4.72 out of 5 average rating, 60 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

The living area features a large, plush leather sofa accompanied by two armchairs. Natural light filters through multiple windows, enhancing the warm wood accents and vaulted ceilings. A round wooden coffee table is positioned centrally on a soft area rug.

5 out of 5 average rating, 58 reviews

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

A spacious living area is highlighted by a stone fireplace with a mounted TV above. Natural light flows through the surrounding large windows, and wooden beams enhance the rustic feel. A staircase leads to an upper loft area, with comfortable seating arranged nearby.