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Vacation rentals in Wintergreen Resort

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Top-rated vacation rentals in Wintergreen Resort

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
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.
Apartment in Wintergreen Resort
4.99 out of 5 average rating, 123 reviews

Endless Mountain Top Views from All The Way Up!

Our warm and inviting condo combines amazing proximity to hiking with to-die-for views of the Blue Ridge Mountains and the horizon 75 MILES distant! Our condo sits a mere 400-yd walk from the closest hiking trail and also has direct access to the ridge line walking area - perfect place for a morning stroll! This updated and modern mountain-themed space features: ✸ Newly renovated! ✸ Stocked modern kitchen! ✸ Two full bathrooms! ✸ Helix Hospitality Mattresses!! ✸ Cozy Fireplace w/ wood provided!

Top 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, 232 reviews

Hottub Ski InOut Renovated Chalet Lower Tyro Slope

Completely renovated, 3 BR/2BA chalet, located on Lower Tyro slope, just below Tequila. Rustic decor, fully stocked kitchen, high end appliances, granite counters. Open floor plan, walls of windows, mtn views. Beautiful stone fireplace, ample comfortable seating. 2 main floor Masters, each w/King bed, TV, luxurious bedding. Loft is a dedicated kids space: 2 sets of bunks, daybed w/trundle, TV & PS4. Gas grill, 6 person hot tub. Perfect ski home to host 2 Families, or a romantic couple's getaway.

Top guest favorite
The living area features large sliding glass doors that open to a stunning view of the mountains. A modern dining table is positioned nearby, illuminated by a pendant light. Comfortable seating is arranged around the room, enhancing the inviting atmosphere.
Condo in Wintergreen Resort
4.98 out of 5 average rating, 127 reviews

Luxury Condo in the Sky! Finest in Wintergreen!

Welcome to our recently renovated luxury condo in the sky! Perched on the edge of the Wintergreen ridgeline, we are just a stone’s throw from nature’s bounty. Our condo offers the perfect blend of relaxation and access to recreation. Hit the ski slopes, take a hike, or explore the bountiful brew and wine scene and then come enjoy the view. The horizon is 75 miles distant from our balcony on a clear day! We love hosting families with kids or couples coming to enjoy all that Wintergreen offers!

Guest favorite
The living area features a comfortable sectional sofa and a wooden coffee table, with a visible fireplace centrally located. Large windows provide natural light and views of the outdoor space. A mounted television is positioned above the fireplace, complementing the cozy ambiance.
Apartment in Wintergreen Resort
4.85 out of 5 average rating, 102 reviews

Wintergreen Getaway

Relax with the whole family at this peaceful place to stay. Enjoy morning coffee and evening cocktails on the deck fronting the golf course. You will love the location and features! Walking distance to spa, The Wintergreen Nature Foundation, and Fire & Frost. Convenient to slopes, Chestnut Springs pool and Upper Shamokin Falls. A great place to relax after a full day of hitting nearby slopes or hiking trails, and exploring Nelson 151's winery and brewery attractions. Stairs to access. WiFi!

Top guest favorite
A scenic view of rolling hills is captured at sunset, with soft hues of orange, pink, and purple coloring the sky. In the foreground, a glass of clear liquid rests on a wooden railing, enhancing the tranquil atmosphere.
Condo in Wintergreen Resort
4.99 out of 5 average rating, 183 reviews

3 BR 3 BA, 2 story condo in Highlands

Newly renovated condo! You can't beat the view from up here. Top floor/vaulted ceilings, next to the Highlands Lift. Just steps from the expert slopes and on the Wintergreen shuttle route. Enjoy hiking, skiing, snowboarding, tubing, outdoor pool time or a local brewery. This condo has 2 master's with king beds, 1 bunk bed (twin over full), a single twin bed and a pull out twin sleeper sofa. The king beds have new high quality mattresses and luxury bedding and a 60" HDTV in living room

Top guest favorite
An open living and dining area showcases warm wooden walls and a colorful area rug. A comfortable seating arrangement includes a sofa with pillows and a coffee table, while a dining table with white chairs is positioned nearby. Large windows allow natural light to fill the space.
Home in Wintergreen Resort
4.95 out of 5 average rating, 238 reviews

Saltbox at Wintergreen, a Modern Mountain Escape

Your mountain adventure awaits at Saltbox, an inviting, eclectic home at Wintergreen Resort in the Blue Ridge Mountains. Combining modern and vintage decor, plus original art, Saltbox was designed to provide escape, inspiration and fun. Nestled at the end of a quiet cul-de-sac drive, with beautiful woods to explore, it's just seconds from the Resort (skiing, tubing, hiking, dining, spa, outdoor movies and more)! Saltbox is the perfect home base for your next getaway, any time of year!

Top guest favorite
A bright and airy living area is highlighted by large windows offering mountain views. A casual seating arrangement features a light-colored sofa and a wooden dining table surrounded by black chairs. Sliding glass doors provide access to an outdoor deck.
Apartment in Rockfish
4.98 out of 5 average rating, 225 reviews

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 Fire & Frost eatery and the Wintergreen Spa, this is an ideal location.

Top guest favorite
Home in Wintergreen Resort
4.97 out of 5 average rating, 123 reviews

Cliffs Edge -A Contemporary Mountain Home

An open floor plan with high ceilings and large skylights, this amazingly engineered home will stun you with its incredible mountain views! This spacious home, with its cantilevered decks, makes this perfect for any family. The large upstairs loft, adjacent to the upstairs bedrooms, offers movies, games, puzzles, and comfortable seating. Wi-Fi, Netflix, and Samsung Smart hub give plenty of entertainment options. The spacious living area and dining room have abundant seating for all.

Superhost
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.
Condo in Wintergreen Resort
4.93 out of 5 average rating, 203 reviews

1 bedroom condo, close to hikes & breweries & pool

Cozy 1BR Wintergreen condo 🌳 🌄 Close to scenic hikes, local breweries and wineries. The resort village, and mountain-top market, just minutes away. Enjoy a fully stocked kitchen, premium coffee and teas, cooking oils and spices. Relax after a day outdoors and enjoy a smart TV, fast WiFi and games. Comfortable queen bed in the bedroom plus new queen sleeper sofa in the living room. Private furnished patio with peaceful wooded views and or cool off in the heated community pool.

Guest favorite
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.
Condo in Wintergreen Resort
4.94 out of 5 average rating, 188 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!

Top guest favorite
Cabin in Vesuvius
4.99 out of 5 average rating, 372 reviews

The Sanctuary

Nature lovers paradise! Named "The Sanctuary" for the place you can UNPLUG, unwind & find your peace! Perched up high on nearly 60 acres- you are sure to get fresh air & the rest you are searching for! Only 4 miles to Wintergreen, 6 miles to Sherando lake and backs up to the Blue Ridge Parkway there are plenty of things to do OR just relax and enjoy the crickets & stars! With crazy careers, growing kids & constant hustle- everyone needs a hide out like this every now and then!

Top guest favorite
A glass of white wine is positioned in the foreground, capturing the warm hues of a sunset. The sun's golden rays reflect off the wine, while silhouettes of trees and distant mountains create a tranquil backdrop in the evening sky.
Condo in Wintergreen Resort
4.99 out of 5 average rating, 272 reviews

Panoramic Sunsets Mountain Views Pool $99 Midweek

SUMMER SPECIAL! Stay 2 nights and get your 3rd night for just $99 when you check in Sunday–Wednesday (select stays, next 60 days). Escape the summer heat and enjoy cooler mountain temperatures, central A/C, a heated outdoor pool, breathtaking sunset views, and two king suites with private en-suite bathrooms. Summer dates are filling fast—book now and experience one of Wintergreen's most sought-after mountain-view condos.

Popular amenities for Wintergreen Resort vacation rentals

GymBBQ grillLaptop-friendly workspaceWifiAir conditioning

Wintergreen Resort house rentals

Guest favorite
A spacious living area features a stone fireplace as the focal point, framed by large windows that offer views of the surrounding trees. A comfortable sectional sofa is arranged around a coffee table, with a television positioned on a media console to the side.
Home in Wintergreen Resort
4.97 out of 5 average rating, 116 reviews

Cozy 5-bedroom home for large gatherings.

Top guest favorite
The exterior of a multi-level home is nestled among trees, with warm lighting illuminating the porch and deck. The spacious deck features a staircase leading down, surrounded by autumn leaves, creating a welcoming atmosphere.
Home in Wintergreen Resort
4.89 out of 5 average rating, 157 reviews

Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat

Top guest favorite
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.
Home in Wintergreen Resort
4.99 out of 5 average rating, 174 reviews

Close to hiking! | King Beds | Fireplace | Hot Tub

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, 148 reviews

Llama Loft | Fire Pit | Fenced Yard | Brew Trail

Guest favorite
A modern living area features a sleek leather sectional sofa adorned with patterned cushions, accompanied by a wooden coffee table. Large windows offer views of the surrounding trees, while natural light enhances the inviting space. A floor lamp adds illumination next to the sofa.
Home in Wintergreen Resort
4.96 out of 5 average rating, 122 reviews

Peaceful 3-BR Mountain home w/Fireplace + Hot tub

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
4.98 out of 5 average rating, 109 reviews

The Cozy Cottage | Mountain views at Wintergreen

Top guest favorite
A wooden walkway leads to the entrance of the house, framed by vibrant pink rhododendron flowers. Tall trees provide a natural backdrop, with dappled sunlight filtering through the leaves, creating a serene outdoor setting.
Home in Wintergreen Resort
4.95 out of 5 average rating, 156 reviews

Bear's Mountain Escape

Guest favorite
The open living area features high ceilings and large windows, allowing natural light to enhance the space. A comfortable seating arrangement includes a sofa and two armchairs, while an adjoining kitchen is visible in the background, equipped with modern appliances.
Home in Nellysford
4.9 out of 5 average rating, 124 reviews

Mountain Bauhaus | Sleeps 8 | Amenities | Grill

Vacation rentals in Wintergreen Resort for a ski trip

Superhost
A wooden staircase is flanked by trees, leading to a brown wooden building with a triangular roof. Large windows allow natural light to enter, surrounded by a peaceful forested area.
Condo in Wintergreen Resort
4.78 out of 5 average rating, 106 reviews

Cozy Condo - Sleeps 4

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
4.95 out of 5 average rating, 175 reviews

Ski-In Ski-Out ~ Mtn Views ~ King Suite

Guest favorite
The multi-story building is nestled among trees, featuring a set of wooden stairs leading to the entrance. Large windows are visible on each floor, allowing natural light to penetrate. A directory sign with multiple unit numbers is displayed at the base of the steps.
Apartment in Roseland
4.82 out of 5 average rating, 250 reviews

Spacious 2 bedroom, 2 bath condo w/ full kitchen

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, 127 reviews

Cozy Cabin+Walk to Ski *Hot Tub* Mtn Vibe

Top 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
4.96 out of 5 average rating, 49 reviews

Wintergreen Mountain Views - Diamond in the Slopes

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, 983 reviews

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

Guest favorite
Townhouse in Wintergreen Resort
4.91 out of 5 average rating, 212 reviews

Wintergreen home, ideal location, dogs welcome!

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, 141 reviews

Family Friendly Home with All Necessities Included

Houses in Wintergreen Resort for a ski trip

Top guest favorite
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.
Home in Wintergreen Resort
5 out of 5 average rating, 39 reviews

Premiere 2 BR Getaway Ski In/Out Wintergreen Condo

Top 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
4.95 out of 5 average rating, 64 reviews

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

Top guest favorite
A snow-covered slope is seen, with skiers and snowboarders enjoying the day. Trees line the edge of the hill, providing a natural border. In the background, multiple buildings are visible, reflecting a ski resort atmosphere under a clear blue sky.
Home in Wintergreen Resort
4.95 out of 5 average rating, 37 reviews

Wintergreen Condo Ski In Ski Out

Guest favorite
Home in Wintergreen Resort
5 out of 5 average rating, 10 reviews

Wintergreen “Dobie Snacks”

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
4.94 out of 5 average rating, 67 reviews

Wintergreen Condo~ 1 Minute To Four Seasons Resort

Top guest favorite
The exterior of a wooden Treeloft home is surrounded by lush greenery, with a gently sloping pathway leading to the front door. The structure features a shaded porch area and large windows that invite natural light while blending with the natural landscape.
Home in Wintergreen Resort
4.97 out of 5 average rating, 31 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
4.98 out of 5 average rating, 44 reviews

Perfect House

Top guest favorite
Home in Wintergreen Resort
5 out of 5 average rating, 16 reviews

Coziest Condo 1st floor, walk to the Patio Terrace

When is the best time to visit Wintergreen Resort?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 1,043ﺩ.ﺇ 1,010ﺩ.ﺇ 760ﺩ.ﺇ 657ﺩ.ﺇ 683ﺩ.ﺇ 646ﺩ.ﺇ 668ﺩ.ﺇ 650ﺩ.ﺇ 646ﺩ.ﺇ 775ﺩ.ﺇ 782ﺩ.ﺇ 970
Avg. temp2°C4°C8°C14°C18°C22°C24°C23°C20°C14°C9°C4°C

Frequently Asked Questions

  • What are the best places to stay in Wintergreen Resort?

    Stay in mountain-side homes, condos, or woodland cottages around Wintergreen Resort. These options have easy access to amenities, scenic views, and outdoor activities, making them frequently suggested for visitors.

  • What are the best things to do in Wintergreen Resort with kids?

    Families can explore nature trails, visit the adventure park for ziplining or mini-golf, and enjoy swimming or skiing when in season. The resort also has craft workshops and special programs for children throughout the year.

  • What are some of the best things to do in Wintergreen Resort?

    Wintergreen Resort has mountain hiking, golf, skiing during winter months, and scenic chairlift rides. Spa experiences, seasonal events, and outdoor dining are also frequently suggested for a well-rounded visit.

  • How is the weather in Wintergreen Resort?

    Wintergreen Resort experiences cool winters around 28–44°F (-2–6°C), and warmer summers near 68–84°F (20–29°C). Spring and autumn are milder, with occasional rainfall and comfortable temperatures.

  • When is the best time to visit Wintergreen Resort?

    Late spring through early autumn is often recommended for hiking, golf, and festivals, while winter draws visitors for skiing and snowboarding. Fall colors and spring blooms offer distinct scenic experiences.

  • What are the best places to visit in Wintergreen Resort?

    Explore the mountain overlooks, nature trails, and the adventure park around Wintergreen Resort. The spa and golf course are also frequently suggested spots for relaxation and recreation.

  • What are some hiking trails in Wintergreen Resort?

    Wintergreen Resort has mountain trails that wind through forested areas and feature scenic outlooks. The Lake Monocan Trail is frequently suggested for gentle walks, while other paths around the resort offer options for varying skill levels.

  • What are some family activities we can do in Wintergreen Resort?

    Families can enjoy swimming, biking, hiking, and mini-golf at Wintergreen Resort. Seasonal programs, craft workshops, and nature exploration are regularly available for all ages.

  • What are some of the best day trip ideas from Wintergreen Resort?

    Plan a visit to nearby vineyards, explore historic towns, or hike in the surrounding Blue Ridge Mountains. Local art galleries and farm markets are also frequently suggested for day trips.

  • Are there any pet friendly accommodations available in Wintergreen Resort?

    Many vacation homes and condos around Wintergreen Resort are pet-friendly, welcoming dogs and other companions. Look for pet-inclusive stays and check for local trails that allow leashed pets.

  • What are some local tips for visiting Wintergreen Resort?

    Pack layers for changing mountain weather and bring sturdy footwear for outdoor activities. Locals suggest booking activities in advance during busy seasons and exploring both forested and open areas for different views.

  • What is Wintergreen Resort known for?

    Wintergreen Resort is known for its mountain recreation, including skiing, snowboarding, hiking, and golf. The area features forested landscapes, scenic overlooks, and family-friendly seasonal events.

  • What are the best hidden gems to explore in Wintergreen Resort?

    Explore lesser-known forest trails, small waterfalls, and quiet picnic spots nestled around Wintergreen Resort. Locally owned art studios and workshops also provide creative experiences beyond the main attractions.

  • What are the best foods to try in Wintergreen Resort?

    Enjoy locally inspired dishes like mountain trout, farm-fresh salads, and seasonal berry desserts at resort restaurants. Virginia wines and regional craft beers are frequently suggested for pairing with meals.

  • What should I bring for a trip to Wintergreen Resort?

    Pack comfortable, weather-appropriate clothing, layered for cooler mornings and warmer afternoons. Bring sturdy shoes for hiking, sunscreen, and swimwear if you plan to enjoy pools or lakes.

  • What is the nightlife in Wintergreen Resort like?

    Wintergreen Resort has relaxed nightlife, including casual bars, lounge areas, and occasional live music events at local venues. Evenings can include outdoor patios or social gatherings around fire pits.

  • What are the most popular events or festivals in Wintergreen Resort?

    Wintergreen Resort hosts music festivals in summer, family-friendly celebrations during holiday weekends, and wine or food tastings throughout the year. Seasonal events draw visitors for mountain activities and outdoor entertainment.

  • Are there family friendly vacation rentals in Wintergreen Resort?

    Wintergreen Resort has many vacation rentals suitable for families, including condos, mountain cottages, and spacious homes. These often feature kitchens, easy access to attractions, and amenities for children.

Quick stats about vacation rentals in Wintergreen Resort

  • Total vacation rentals

    Explore 770 vacation rentals in Wintergreen Resort

  • Nightly prices starting at

    Wintergreen Resort vacation rentals start at ﺩ.ﺇ 257 per night before taxes and fees

  • Verified guest reviews

    Over 28,350 verified reviews to help you choose

  • Family-friendly vacation rentals

    580 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 260 rentals that welcome pets

  • Vacation rentals with a pool

    500 properties feature pools

  • Rentals with dedicated workspaces

    240 properties have a dedicated workspace

  • Wi-Fi availability

    770 of Wintergreen Resort vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Wintergreen Resort rentals

  • 4.9 Average rating

    Wintergreen Resort stays are highly rated by guests—averaging 4.9 out of 5!

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