Ski-in/Ski-out holiday rentals in Wintergreen Resort

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.

4.98 out of 5 average rating, 207 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.

4.96 out of 5 average rating, 737 reviews

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

Cozy Mountain Cabin

Snuggled in the Blue Ridge. Secluded from the crowds. Experience your visit in an authentic log cabin. Spacious sleeping loft. Perfect romantic escape, friends getaway, or personal retreat. Workout area/sitting room. Fresh eggs (in season), wine, tea, coffee. 1G Internet, SMART TV. A/C. Less than 2 miles to Devil's Backbone and Bold Rock. Minutes from App. Trail, Wintergreen Resort, breweries, wineries, cideries, restaurants, horseback riding, hiking trails, outdoor concerts, & antique shopping.

A cozy living area features a light-colored sofa and an accent chair positioned around a round, woven coffee table. A textured area rug adds warmth to the space, while a stacked stone fireplace serves as a focal point, complemented by tall windows allowing natural light.

4.98 out of 5 average rating, 89 reviews

Base Camp Condo

Indulge in the enchanting seasons of Wintergreen, Virginia, with this quaint 2-bed, 2-bath Airbnb retreat. Just minutes from the heart of Wintergreen resort and walking distance to the slopes, market, and restaurants, this recently renovated mountain escape is waiting to be your next adventure base camp. This cozy haven provides a year-round escape just minutes off the Blue Ridge Parkway, inviting you to experience the diverse charm of Virginia in every season. We look forward to hosting you!!

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.

4.97 out of 5 average rating, 118 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!

5 out of 5 average rating, 954 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

Experience glamping, Blue Ridge style. Our luxury yurt is located at the top of a small hill, in the center of a 70 acre farmstead surrounded by natural beauty. Night Archer Farm is located off a quiet country road in Afton, Nelson County. It is private, but not remote. You are close to the Brew Ridge trail, wineries, breweries, skiing at Wintergreen, Blue Mountain Brewery, Devil's Backbone, golf, hiking, or driving the Blue Ridge Parkway. Hike directly from the Yurt up into the mountains!

An inviting exterior of a two-story home is presented, featuring a blend of wood and stone accents. Large glass windows provide natural light, and snow blankets the ground, creating a serene winter atmosphere. A sloped driveway leads to the entrance, surrounded by trees.

4.85 out of 5 average rating, 124 reviews

Walk to Ski! HotTub PoolTable Shuffleboard Dogs OK

8min walk or 3min drive to ski. 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 $187.

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.

4.99 out of 5 average rating, 172 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

4.96 out of 5 average rating, 165 reviews

1 bedroom condo, walk to the slopes !

Cozy 1BR Wintergreen condo ⛷️❄️ 5-minute walk to the ski slopes, resort village, and mountain-too market, with snow tubing only minutes away. Enjoy a fully stocked kitchen, premium coffee and teas, cooking oils and spices. Relax by the wood burning fire 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 close access to the village for après-ski.

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.

4.91 out of 5 average rating, 153 reviews

Cozy Comfort with a View - Wintergreen Resort

Our private, spacious, dog friendly condo is just a 5 minute walk to the main lodge with shops, restaurants, and of course the slopes! Shuttles run during ski season as well. Beautiful hiking trails are just outside the door, and a short drive will get you to the Blue Ridge Parkway, Crabtree Falls, Stoney Creek Golf Course, and the famous Route 151 with Virginia's finest breweries and wineries. There is a community pool available in Wintergreen Resort during the summer months.

Flat in Wintergreen Resort

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.

4.97 out of 5 average rating, 106 reviews

Mountain View Nest

From the moment you walk in, this condo offers endless opportunities to relax and retreat. The sweeping mountain views over the back deck provide the ideal setting for a romantic getaway, a girls weekend, or much needed time to recharge. This one bedroom/bathroom unit with a king sized bed, fully stocked kitchen, and artistic decor is located on the third floor of the Ledges. It is the perfect location for those who ski, hike, golf, or taste the flavors from local wineries.

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, 146 reviews

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

Just steps from Wintergreen Resort’s slopes, Slope Side Gem offers the perfect mountain escape! Located in the heart of Mountain Village next to the Mountain Inn, you’re just a short walk to Starbucks, The Market, shops, and three restaurants and bars. Whether you’re skiing, hiking, golfing, or enjoying a local brewery or winery, adventure is at your doorstep. After an exciting day, unwind on the private balcony and take in the breathtaking 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.

4.92 out of 5 average rating, 115 reviews

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

Renovated 3BR/2.5BA mountain home is just a short walk to ski slopes, hiking trails, and resort amenities. Enjoy a private hot tub, stone fireplace, deck with views, gas fire pit, and grill. Kids will love the bunk room and loft with Buck Hunter arcade & games. Smart TVs with streaming in main living and bunk room. Fully stocked kitchen + washer/dryer. Perfect for ski trips, hiking getaways, winery weekends, or a relaxing mountain escape

Popular amenities for Wintergreen Resort ski-in/out rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Ski-in/out house rentals

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, 30 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.

4.95 out of 5 average rating, 56 reviews

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

5 out of 5 average rating, 7 reviews

Cool Mountain Breezes on The Slopes

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.

4.94 out of 5 average rating, 62 reviews

Wintergreen Condo~ 1 Minute To Four Seasons Resort

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.

4.95 out of 5 average rating, 21 reviews

Perfect house

4.84 out of 5 average rating, 55 reviews

WalktoSki! 300 Yards from Eagles Swoop! Cozy Cabin

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, 67 reviews

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

The exterior of the home is framed by tall, bare trees, showcasing a modern gray structure. A prominent stone chimney rises above the gabled roof. Wooden decks and steps lead up to the entrance and wrap around the structure, offering access to scenic views.

4.93 out of 5 average rating, 42 reviews

Walk to Ski! Magnificent Mntn View Stone Fireplace

Family-friendly, ski-in/out home rentals

An open living area features a sectional sofa in light grey, arranged around a round wooden coffee table. A sleek black television is mounted above a modern fireplace. Large windows provide natural light, while a ceiling fan and wall art enhance the space.

5 out of 5 average rating, 9 reviews

Steps to the Slopes-Relax in comfort

A comfortable living room setting features a large sofa with plush throws and cushions, a reading lamp beside an armchair, and a wooden coffee table with magazines. A fireplace constructed of stone is prominently displayed against the wall, with stacked firewood nearby.

4.84 out of 5 average rating, 79 reviews

Cozy condo! Short walk to the slopes and trails.

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.

4.88 out of 5 average rating, 17 reviews

Wintergreen Condo Ski In Ski Out

Townhouse in Wintergreen Resort

An open-plan living area is highlighted by natural light, featuring a comfortable seating arrangement and a modern kitchen island. Bar stools are positioned at the counter. Floor-to-ceiling windows offer views of the surrounding greenery, enhancing the spaciousness.

4.94 out of 5 average rating, 36 reviews

Wild Ridges - Newly Renovated!

Flat in Wintergreen Resort

A cozy living area is present, featuring a spacious sectional sofa adorned with colorful throw pillows. A coffee table is positioned centrally, and a large flat-screen television is mounted on the wall. Natural light streams through expansive windows, highlighting the warm wood accents.

4.8 out of 5 average rating, 5 reviews

Slope-Side with a Mountain View

4.93 out of 5 average rating, 29 reviews

A loft-style living area is presented, featuring a comfortable sofa with plaid accent pillows and a wooden coffee table. The kitchenette area is visible, equipped with wooden cabinets and essential appliances. A staircase leads to a sleeping loft, adding verticality to the space.

Apartment in Roseland

Great location! Steps from dining/ event spaces!

A wooden pathway leads to a rustic cabin nestled among trees, with soft lighting illuminating the entrance. An American flag hangs outside a window, while warm light spills from the interior, inviting guests to explore the surrounding nature.

Chalet in Wintergreen Resort

4.84 out of 5 average rating, 62 reviews

House on the Slopes (Ski-in /out)

The view from the condo features a snowy landscape framed by bare trees. Below, skiers can be seen navigating the slopes, while the Blue Ridge Express lift station is visible in the distance, surrounded by the mountains under a partly cloudy sky.

5 out of 5 average rating, 3 reviews

NEW! Slopeside Condo Ski In/Out - 4 bed 3 bath

Ski-in/out cabin rentals

The exterior of a mid-century modern home is surrounded by lush greenery. A spacious deck wraps around the side, featuring a mix of railings and a balcony. The building is designed with asymmetrical angles and large windows, inviting natural light into the interior.

4.86 out of 5 average rating, 44 reviews

Bide-a-Wee- Hike the Trails! Close to the slopes!

4.59 out of 5 average rating, 34 reviews

Cozy 'Hillside Hideaway' in Wintergreen Resort!

The home is set against a backdrop of snowy trees, illuminated by warm light from the windows. The structure is elevated, showcasing the exterior under frosty conditions, with snow covering the ground and branches.

4.84 out of 5 average rating, 38 reviews

A warm mountain top home, steps from the slopes.

A deck is shown with black wrought iron furniture, including a small table and chairs. Fallen leaves are scattered on the wooden surface. Surrounding trees display autumn foliage, revealing distant mountain views under a cloudy sky.

4.93 out of 5 average rating, 40 reviews

Eagle's Lookout Retreat at Wintergreen Resort, VA

A cabin nestled amidst vibrant autumn foliage, surrounded by towering trees adorned with golden leaves. The home features a wooden deck and is approached by a gravel driveway, inviting guests to enjoy the serene natural setting.

4.98 out of 5 average rating, 57 reviews

Leaf-Peeping at Oak Ledge! Trails+Tastings+Peace

A spacious living area is highlighted by large glass doors that offer views of a covered porch. A fireplace is situated beneath a wall-mounted television, while natural light fills the room. Warm wood flooring and a rustic coffee table enhance the inviting atmosphere.

4.45 out of 5 average rating, 78 reviews

Smoky Bear Cabin

A two-story cabin is nestled among trees, showcasing a sloped roof with multiple gables. A wooden walkway leads to the entrance, flanked by greenery. Large windows allow for natural light, contributing to a warm, inviting appearance.

4.73 out of 5 average rating, 82 reviews

Slope Side Suite