Condo vacation rentals in Wintergreen Resort

A cozy living area features natural stone accents around a wood-burning fireplace. A small dining table with two chairs is positioned near large windows, allowing ample natural light. Green accent walls enhance the inviting atmosphere, while a comfortable seating area is visible nearby.

4.89 out of 5 average rating, 210 reviews

Tips Up: Cozy Slopeside Retreat w/ Fireplace

The mountains are calling and you must go. Well, you don't have to, but we think it's a good idea. Make Tips Up your home while you're away. With slopeside views, a cozy and comfortable ambiance, and close proximity to skiing (only 100 yards from the slopes!) and hiking, this 1B/1BA condo is the perfect getaway for outdoor enthusiasts seeking a mountain escape. Relax at nearby breweries and wineries with unbeatable views, and return to your condo to enjoy the amenities of Wintergreen Resort.

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.

4.99 out of 5 average rating, 268 reviews

Sunset Vista Villa, Mountain Views-Close to Slopes

Welcome to Sunset Vista Villa, Mountain Views & Close to Slopes (on the shuttle route) This beautiful, 2 bedroom, 2 bath, first-floor-unit with top story mountain views, is near all amenities the Wintergreen Resort has to offer. It comfortably sleeps five and with its western vistas, sunsets are a thing to behold! Whether you spend your days hiking, skiing or enjoying the wineries and breweries, SVV will enhance your stay. Book today & come enjoy the Wintergreen Resort and Blue Ridge Mountains!

A spacious great room is featured, furnished with a comfortable brown leather sofa and accent chairs. Large panoramic windows provide expansive views of the Blue Ridge Mountains, while a dining area with a table for six is positioned nearby. Warm wood flooring enhances the inviting space.

4.98 out of 5 average rating, 124 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.

The two-story condo features a warm wood exterior, framed by lush greenery and trees. Wide wooden steps lead to the entrance, giving access to individual balconies that enhance the inviting appearance of the building.

4.96 out of 5 average rating, 347 reviews

Five Minute Walk to Everything!

**Pet friendly** two bedroom, two bath, loft style condo centrally located at Wintergreen Resort. Ski check-in/lifts, restaurants, the mountaintop provisions market, and the Mountain Inn and conference center are all within a 5 minute walk! This is a two-story unit with loft style bedroom and en suite bath, and first floor bedroom with hall bath. Parking, pool access, washer/dryer, and Wi-Fi included. Fully stocked kitchen, wood burning fireplace, balcony, all towels/linens provided. Sleeps 5.

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.

4.98 out of 5 average rating, 122 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!

A private balcony features wooden railings, with a light dusting of snow on the ledge. Lush pine trees stand prominently in the background, contrasting against a clear blue sky and hints of distant landscape, contributing to a serene outdoor viewing experience.

4.97 out of 5 average rating, 165 reviews

2-min drive to resort, stair-free/free firewood!

Peaceful, recently renovated mountain-top retreat. Relax or work from home. End your day with a hike or spa treatment around the corner—linger with a glass of wine at sunset. It’s all only a 2 minute walk from the front door. Welcome to our mountain home! 2-3 min drive from ski lifts/resort, hiking Free firewood (seasonal) Family games & smart TVs (no cable) for movie night (must sign into your own subscriptions) Smartlock entry Stair-free entry *outdoor HOA pools CLOSED for season

The exterior of a two-story cabin houses warm wooden accents and large windows. The entrance features a welcoming set of wooden steps leading up to a balcony, surrounded by tall trees, with a concrete pathway leading toward it.

4.94 out of 5 average rating, 246 reviews

Eight Minute Walk to Everything

This one-bedroom, one-bath condo is centrally located. Ski check-in, restaurants, the mountaintop provisions market, and the Mountain Inn and conference center are all within an 8 minute walk. It's a one-story, downstairs unit that includes a back porch with just a few steps down to the ground. Perfect for taking the dog outside in the pet-friendly space. Full kitchen and dishes, wood-burning fireplace, balcony, and all towels and linens are provided for your convenience. Sleeps 3.

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, 179 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, 188 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.

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.

4.96 out of 5 average rating, 165 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!

A cozy living area features a blue couch facing a wood-burning fireplace, with a flat-screen TV mounted above. A side chair provides additional seating. Natural light filters through large windows, illuminating a small coffee table adorned with a vase of yellow tulips.

5 out of 5 average rating, 100 reviews

Cozy Laurelwood condo - 10 min walk to slopes

This beautiful 1-bedroom, 1-bath Laurelwood condo is perfectly located just a short walk from the pool, market, coffee shop, restaurants, and the Wintergreen Conference Center. Inside, you’ll find a fully equipped kitchen, a cozy wood-burning fireplace (with complimentary firewood), and a spacious king-size bed. Step outside to your private deck and enjoy the peace of the surrounding forest—an ideal retreat for relaxation and comfort.

A cozy living room is presented, featuring two plush leather sofas, a coffee table, and a fireplace. Natural light enters through large windows, and decorative accents enhance the warm ambiance. A flat-screen TV sits on a stand, completing the inviting space.

4.98 out of 5 average rating, 200 reviews

Cozy getaway with heated floors

Step into a beautifully crafted retreat where a stunning live-edge oak breakfast bar with leather stools awaits. Enjoy the elegance of granite countertops and sleek stainless steel appliances. The cozy living room, with its plush leather sofas and a warm fireplace, offers the perfect spot to relax. Accommodating up to 2 guests, you'll find a luxurious queen bed. Radiant heated floors add an extra touch of comfort throughout your stay.

Popular amenities for Wintergreen Resort condo rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Condo rentals with a hot tub

A spacious living area is presented with large windows offering natural light and views. Comfortable seating is arranged around a wooden coffee table, with a cozy armchair and leather sofa. A stone fireplace adds warmth, complementing the light wood flooring and neutral color palette.

Overlook 26 with Wintergreen Advantage

The exterior of the condo is surrounded by mature trees and greenery. A paved path leads to the entrance, with steps visible. A gazebo appears in the distance, providing a shaded gathering area. The scene captures a tranquil setting with soft lighting.

5 out of 5 average rating, 14 reviews

Ski-In/Ski-Out Wintergreen Resort Condo + Hot Tub!

A spacious living area features a large sectional sofa arranged around a round coffee table. Panoramic windows offer scenic views of the surrounding landscape, while wood accents and a stone fireplace add warmth and comfort. Natural light floods the room through skylights.

Vistas 82 with Wintergreen Advantage

Highridge Court 30 with Wintergreen Advantage

A comfortable living area is arranged with a dark brown sofa, a blue couch, and a cozy ottoman. Natural light fills the space through large glass doors that open to a balcony with scenic views. Subtle artwork and lamps complement the warm tones of the room.

Highlands 37 with Wintergreen Advantage

Diamond Hill 49 with Wintergreen Advantage

5 out of 5 average rating, 3 reviews

Timbers Lodge 39 with Wintergreen Advantage

A cozy living area features a large mural of misty mountains and trees on the wall. A spacious gray sofa is positioned in front of a wooden coffee table on a textured area rug. Natural light fills the room through a sliding glass door, with a small side table and potted plants enhancing the decor.

5 out of 5 average rating, 4 reviews

Mountain Inn Lodge 63 with Wintergreen Advantage

Condo rentals with a pool

A cozy living area features a light-colored sofa with decorative cushions. A wooden coffee table sits in front, accompanied by an accent chair. A fireplace is positioned against the wall, and large windows allow natural light to illuminate the space, overlooking lush greenery.

4.92 out of 5 average rating, 59 reviews

2 br/2 b condo; skiing; hiking; wineries; pool

Two reclining chairs are positioned in a cozy living area, complemented by a warm orange wall. A dining area with a wooden table is visible in the background, along with large glass doors that provide natural light and access to a terrace overlooking greenery.

4.9 out of 5 average rating, 40 reviews

On the mountain, pet and child friendly

4.95 out of 5 average rating, 19 reviews

Wintergreen Ski Retreat, Cozy Condo Near Slopes

A spacious living area features a comfortable sofa, a wooden coffee table, and a well-lit dining space. Large windows allow natural light to fill the room, and a fireplace adds warmth. Colorful artwork adorns the walls, complementing the light-toned flooring.

4.89 out of 5 average rating, 66 reviews

Wintergreen! Dog friendly, cozy and comfortable

A deck features two comfortably arranged chairs with cushions, overlooking expansive views of the Blue Ridge Mountains. Clear skies are visible, and the natural landscape extends into the distance, highlighting the serene outdoor setting.

4.97 out of 5 average rating, 33 reviews

Recently updated - views of the Blue Ridge Mtns

A spacious balcony offers outdoor seating with a glass-top table and four metal chairs. Expansive mountain views extend beyond the boundary, showcasing rolling hills under a clear blue sky.

4.59 out of 5 average rating, 98 reviews

Amazing views! Overlooking Expert Slope

4.99 out of 5 average rating, 81 reviews

A Mountain Escape-Cozy Condo for 2 to 4

The bedroom features a spacious bed dressed in soft, plaid linens, with a decorative throw pillow placed against a padded headboard. A bedside lamp provides gentle illumination, while windows allow natural light to fill the room.

4.94 out of 5 average rating, 80 reviews

360° Views of the Slopes and Mountains

Weekly condo rentals

A modern kitchen showcases sleek brown cabinets and stainless-steel appliances, complemented by a granite countertop. Pendant lights hang above bar seating with wooden chairs. Open shelving displays decorative items, and natural light filters in through nearby windows, enhancing the cozy ambiance.

4.97 out of 5 average rating, 69 reviews

Ty's Retreat: Cozy 2-bedroom condo with fireplace

4.89 out of 5 average rating, 37 reviews

A bright living area features a comfortable gray sectional sofa and various seating options, including a patterned chair. A large flat-screen TV is mounted above a black fireplace, with daylight filtering through expansive windows that showcase views of surrounding nature.

Condo in Massies Mill

Mountain Top Getaway

A vibrant sunset displays a gradient of orange, pink, and purple hues over distant mountains. The sun sets gently on the horizon, with silhouettes of trees framing the scene, creating a serene and picturesque view.

4.85 out of 5 average rating, 73 reviews

Fireworks & Mountain Views Ski In/Out Studio in WG

An open dining area features a large wooden table surrounded by leather chairs. A granite countertop separates the dining space from the kitchen. Light fixtures cast soft patterns on the ceiling, while large windows provide views of the surrounding greenery.

4.89 out of 5 average rating, 36 reviews

Condo w/ Full Kitchen, Balcony, King & Queen Beds

The living area is designed with an open layout, featuring a spacious sectional couch and a wooden coffee table. Two bar stools are positioned at a high table, and decorative paddles adorn the wall above. A staircase leads to the upper level, while light floods the space, enhancing its cozy ambiance.

4.9 out of 5 average rating, 41 reviews

Ski-in/Ski-out condo Pet-OK Steps from Wintergreen

The living area features large windows allowing natural light to illuminate the space. A sectional sofa, leather chairs, and a coffee table are arranged around the wood-burning fireplace. A dining table with wooden chairs is visible, alongside a view of the outdoors through the sliding glass doors.

4.94 out of 5 average rating, 64 reviews

Sitting on the 18th fairway

The living area features a large sectional sofa facing a stone fireplace, with a wooden accent wall above. Floor-to-ceiling windows provide expansive views of the surrounding forest and mountains. A dining table and four chairs sit nearby, with stylish decor enhancing the inviting atmosphere.

5 out of 5 average rating, 45 reviews

Lovely Ski Front Private 3-bed/3-bath condo

A balcony view captures a serene sunset over snow-covered mountains, with hues of orange and purple in the sky. String lights adorn the railing, and a warm beverage is held in one hand, creating a peaceful ambiance.