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Wintergreen Resort vacation rentals

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Wintergreen Resort vacation rentals

Self check-in
Gym
BBQ grill
Laptop-friendly workspace
Wifi

Wintergreen Resort house rentals

Top guest favorite
A private in-ground swimming pool is surrounded by a wooden deck and sun loungers. Shade is provided by a canopy, and lush greenery is visible in the background, highlighting the calming outdoor setting. The pool features a net for recreational activities.
Home in Lovingston
4.96 out of 5 average rating, 212 reviews

Cottage on the Knoll ~ Prvt Pool & Hot Tub OPEN

Top guest favorite
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
4.97 out of 5 average rating, 118 reviews

Llama Loft | Low Fees | Darts | Fire Pit | Off 151

Guest favorite
A living room area features a queen sofa bed, accented with decorative cushions. A small green side table is positioned beside a cozy armchair. A colorful area rug lays on the floor, and wall art depicting a serene forest scene adds visual interest. Natural light enters from a nearby window.
Home in Wintergreen Resort
5 out of 5 average rating, 5 reviews

Casa Perfecta

Top guest favorite
A dining area features a rustic wooden table surrounded by modern chairs. Large glass windows showcase panoramic mountain views, while natural light illuminates the space. A stylish floor lamp adds warmth, complementing the cozy décor of the nearby seating area.
Home in Wintergreen Resort
4.99 out of 5 average rating, 91 reviews

The Cozy Cottage | Mountain views at Wintergreen

Guest favorite
The farmhouse exterior is set among autumn foliage, framed by trees with colorful leaves. Large windows dominate the front, allowing natural light to fill the interior. A gravel driveway leads to the welcoming entrance, showcasing the welcoming style of the home.
Home in Wintergreen Resort
4.89 out of 5 average rating, 66 reviews

Hot Tub EV Charger Mntn View Fireplace Grill Pool

Top guest favorite
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
4.99 out of 5 average rating, 115 reviews

Wooded Haven | Family Friendly | Fire Pit | Trail

Top guest favorite
The exterior of a cozy two-story mountain house is visible, featuring brown wooden siding and large windows. Leaves cover the ground, and a gravel driveway leads up to the home, surrounded by trees displaying autumn foliage.
Home in Wintergreen Resort
4.99 out of 5 average rating, 102 reviews

Cozy, relaxing mountain getaway on the golf course

Guest favorite
The exterior of a designer home features large windows that provide expansive views. A hot tub and a cedar barrel sauna are positioned on the spacious deck, surrounded by seating areas and greenery, creating a welcoming outdoor space.
Home in Wintergreen Resort
4.95 out of 5 average rating, 65 reviews

Designer Home w/ Incredible Views, Sleeps 16

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Wintergreen Resort condo rentals

Guest favorite
A waterfall cascades gracefully down rocky terrain, surrounded by bare trees and earthy tones of late winter. The water glistens as it flows over the moss-covered stones, creating a serene natural setting that blends with the surrounding forest.
Condo in Wintergreen Resort
5 out of 5 average rating, 14 reviews

Retreat @ 3 Ridges | 3min->Slopes | Walk to Dining

Top guest favorite
A breathtaking vista showcases undulating mountain ranges blanketed in frost, with trees shimmering in icy white. The expansive sky features a mix of clouds and sunlight, creating a dynamic backdrop against the winter landscape.
Condo in Wintergreen Resort
4.95 out of 5 average rating, 299 reviews

Five Minute Walk to Everything!

Guest favorite
A stone fireplace with a sleek, dark frame anchors the living area, complemented by a natural wood mantel. A large wall-mounted TV is positioned above. A light-colored sectional sofa and coffee table create a welcoming seating arrangement, with a large window providing views of the snowy slopes outside.
Condo in Wintergreen Resort
4.92 out of 5 average rating, 26 reviews

Wintergreen Mountain Views - Diamond in the Slopes

Guest favorite
An outdoor terrace is furnished with a round metal table surrounded by six black wicker chairs. The railing offers a view of distant hills, with trees visible in the background under a clear sky.
Condo in Wintergreen Resort
4.88 out of 5 average rating, 113 reviews

1720 High Ridge at Wintergreen Resort

Guest favorite
A ski lift station is positioned atop a hillside, featuring a modern design with a large roof and glass panels. The surrounding landscape showcases rolling mountains in the distance, under a clear blue sky, with a gravel path leading up to the station.
Condo in Wintergreen Resort
4.91 out of 5 average rating, 177 reviews

Tips Up: Cozy Slopeside Retreat w/ Fireplace

Superhost
Condo in Wintergreen Resort
4.88 out of 5 average rating, 163 reviews

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

Guest favorite
A serene winter landscape captures snow-covered mountains under a colorful sunset. The scene includes a gently sloping ski hill, illuminated by soft lights, alongside a cluster of buildings nestled in the valley, framed by wooded areas surrounding the terrain.
Condo in Wintergreen Resort
5 out of 5 average rating, 26 reviews

Love of mountains oh fill my cup

Top guest favorite
An entrance hallway is featured with a welcoming atmosphere. A mirror is mounted on the wall opposite a wooden door with frosted glass. A closet with white slatted doors offers ample storage space. A textured runner rug adds color to the wooden floor.
Condo in Wintergreen Resort
5 out of 5 average rating, 39 reviews

The Perch in Wintergreen Laurelwood

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

Superhost
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.
Condo in Wintergreen Resort
4.72 out of 5 average rating, 144 reviews

Mountain Views

Top guest favorite
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
5 out of 5 average rating, 918 reviews

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

Guest favorite
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.
Townhouse in Wintergreen Resort
4.94 out of 5 average rating, 185 reviews

Fantastic home in an ideal location, dogs welcome!

Top guest favorite
A functional entryway features a built-in mudroom with hanging hooks for jackets and ample storage shelves. Ski equipment is displayed prominently on the right, while a framed wall art piece adds a touch of character to the space.
Chalet in Wintergreen Resort
5 out of 5 average rating, 52 reviews

Mountain Views, Hiking, Ski-Out @ Tyro

Guest favorite
A spacious bedroom features a high, wood-beamed ceiling and a large window providing natural light. The bed is dressed in navy bedding with a plaid blanket draped across it. A wooden dresser and lamp complement the rustic decor, and a mounted TV is positioned above.
Home in Wintergreen Resort
4.97 out of 5 average rating, 198 reviews

Hottub Ski In/Ski Out Renovated Chalet Lower Tyro

Top guest favorite
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.
Cabin in Wintergreen Resort
4.99 out of 5 average rating, 135 reviews

Family Friendly Home with All Necessities Included

Top guest favorite
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.
Condo in Wintergreen Resort
4.9 out of 5 average rating, 144 reviews

Cozy Comfort with a View - Wintergreen Resort

Top guest favorite
The gravel pathway leads to a charming log cabin, framed by tall trees and surrounded by greenery. A sign reading 'COZY MOUNTAIN CABIN' is positioned near the path, inviting visitors to explore this secluded retreat in the Blue Ridge.
Cabin in Roseland
4.96 out of 5 average rating, 703 reviews

Cozy Mountain Cabin

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Quick stats about vacation rentals in Wintergreen Resort

  • Total rentals

    670 properties

  • Nightly prices starting at

    R1,245 ZAR before taxes and fees

  • Total number of reviews

    25K reviews

  • Family-friendly rentals

    520 properties are a good fit for families

  • Pet-friendly rentals

    220 properties allow pets

  • Rentals with a pool

    420 properties have a pool

Frequently Asked Questions

  • What types of vacation rentals are available in Wintergreen Resort?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Wintergreen Resort. From over 310 condo rentals to over 220 house rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.

  • Are there vacation rentals with a dedicated workspace in Wintergreen Resort?

    Yes! Work meets play with ease at over 240 vacation rentals in Wintergreen Resort featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Wintergreen Resort?

    Four-legged friends are welcome in Wintergreen Resort. Choose from more than 220 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in house rentals in Wintergreen Resort?

    Experience the best of Wintergreen Resort with our house rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there Wintergreen Resort house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 110 house rentals with pools in Wintergreen Resort, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Wintergreen Resort have self check-in?

    Absolutely! We offer over 90 house rentals with self check-in in Wintergreen Resort. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Wintergreen Resort have wireless internet?

    Absolutely! We offer over 220 house rentals with wireless internet in Wintergreen Resort. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Wintergreen Resort have a gym?

    Absolutely! We offer over 40 house rentals with a gym in Wintergreen Resort. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Wintergreen Resort have a bbq area?

    Absolutely! We offer over 90 house rentals with a bbq area in Wintergreen Resort. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Wintergreen Resort?

    Wintergreen Resort has more than 220 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

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