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Vacation rentals in Wintergreen Resort

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Vacation rentals for every style

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Popular amenities for Wintergreen Resort vacation rentals

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

Wintergreen Resort house rentals

Top guest favorite
An outdoor deck features a cozy fire pit surrounded by comfortable seating. The scene is tranquil with trees in the background, and a colorful sunset sky enhances the atmosphere. Soft lighting along the railing adds a welcoming touch.
Home in Wintergreen Resort
5 out of 5 average rating, 24 reviews

Luxury|Hot Tub|Sauna|Cold Plunge|Game Room|Views

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
4.95 out of 5 average rating, 215 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
4.98 out of 5 average rating, 121 reviews

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

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, 93 reviews

The Cozy Cottage | Mountain views at Wintergreen

Top guest favorite
The home's modern architecture is illuminated against the night sky, showcasing angular lines and large windows. Natural elements surround the property, with trees reflecting the warm glow from the interior lights and highlighting the peaceful setting.
Home in Nellysford
4.97 out of 5 average rating, 153 reviews

Glass House | Mountain & Water Views @ Wintergreen

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, 118 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
A hot tub is positioned on a wooden deck, surrounded by lush greenery and trees. The serene view of the mountains is visible in the distance, complementing the tranquil setting. Steps lead to the hot tub, creating easy access.
Home in Wintergreen Resort
4.81 out of 5 average rating, 161 reviews

Misty Mountain Cabin w/spa

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

Guest favorite
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.
Condo in Wintergreen Resort
4.96 out of 5 average rating, 137 reviews

Mtn/Firework Views from Private Deck ~ King Suite

Top guest favorite
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.
Chalet in Wintergreen Resort
4.92 out of 5 average rating, 108 reviews

Summer Pool+Walk to Ski *Hot Tub* Mtn Vibe

Guest favorite
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.
Condo in Wintergreen Resort
4.93 out of 5 average rating, 28 reviews

Wintergreen Mountain Views - Diamond in the Slopes

Top guest favorite
A table set for two features a bottle of sparkling beverage and two glasses, accompanied by an elegant plate of appetizers. The backdrop showcases expansive mountain views under a bright sky, enhancing the serene atmosphere of the outdoor dining area.
Apartment in Wintergreen Resort
4.97 out of 5 average rating, 91 reviews

Mountain View Nest

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, 923 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, 187 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, 57 reviews

Mountain Views, Hiking, Ski-Out @ 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

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Ski-in/ski-out houses in Wintergreen Resort

Guest favorite
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.
Home in Wintergreen Resort
5 out of 5 average rating, 18 reviews

Wintergreen condo ski-in/ski-out

Top guest favorite
A cozy living area is centered around a rustic fireplace, enhanced by warm wood accents. Stockings hang from the mantle, while a plush sectional sofa offers ample seating. Natural light streams in through large windows, highlighting the tranquil atmosphere of the space.
Home in Wintergreen Resort
5 out of 5 average rating, 22 reviews

Premiere 2 BR Getaway Ski In/Out Wintergreen Condo

Guest favorite
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.
Home in Wintergreen Resort
4.94 out of 5 average rating, 51 reviews

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

Top guest favorite
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.
Home in Wintergreen Resort
4.93 out of 5 average rating, 59 reviews

Wintergreen Condo~ 1 Minute To Four Seasons Resort

Superhost
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.
Home in Wintergreen Resort
4.71 out of 5 average rating, 66 reviews

Cliff Hanger Hot Tub Dogs OK Pool Tennis Golf Hike

Superhost
Home in Wintergreen Resort
4.83 out of 5 average rating, 6 reviews

The Distinguished Squirrel Chalet walking distance

Top 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, 7 reviews

Casa Perfecta

Superhost
A spacious living area is highlighted by high vaulted ceilings and a cozy wood-burning fireplace. Large glass doors invite natural light, opening to a view of the greenery outside. A spiral staircase leads to an upper loft, offering additional living space. Two lamps provide soft illumination.
Home in Wintergreen Resort
4.81 out of 5 average rating, 48 reviews

Cozy cabin/BeautifulFoliage/FantasticHikes/PupsOK!

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Quick stats about vacation rentals in Wintergreen Resort

  • Total rentals

    670 properties

  • Nightly prices starting at

    G$14,629 GYD before taxes and fees

  • Total number of reviews

    25K reviews

  • Family-friendly rentals

    520 properties are a good fit for families

  • Pet-friendly rentals

    240 properties allow pets

  • Rentals with a pool

    410 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 290 condo rentals to over 230 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 260 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 240 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 $100 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 120 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 230 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 230 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

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