Condo vacation rentals in 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, 259 reviews

Sunset VistaVilla, 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!

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.

4.95 out of 5 average rating, 328 reviews

Five Minute Walk to Everything!

**Pet friendly** two bedroom, two bath, loft style condo centrally located at Wintergreen Resort. Ski check-in, 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 master 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.

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, 122 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 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, 115 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 cozy living room features comfortable seating on a sofa and armchair, complemented by a round coffee table. A smart TV is positioned above a fireplace with subtle artwork on the wall. Natural light filters through large windows, enhancing the inviting atmosphere.

4.99 out of 5 average rating, 100 reviews

Stylish*Updated*Central*Walk to Slopes*Dogs OK!

Step into the allure of our fantastic Wintergreen, just a leisurely 4min stroll away from the heart of Wintergreen's mtn action! Tucked away in a serene and tranquil nook of the mountain, our meticulously curated property combines serene relaxation with unfettered access to the thrilling outdoor adventures that await nearby. The closest hiking trail is within 200 yds! Whether you're a couple seeking a romantic retreat or a small, fun family, our home is eager to embrace your mountain dreams!

A spacious living area features a wood-burning fireplace surrounded by light-colored walls. A comfortable couch, adorned with a welcoming throw pillow, faces a wooden coffee table. Natural light enters through large windows, offering views of the outdoor greenery.

4.93 out of 5 average rating, 239 reviews

The Modern Mountain Condo

Conveniently located within the 4-season Wintergreen Resort, this recently renovated condo offers a quiet and cozy stay while you take in the mountain views and enjoy endless outdoor activities, wineries, breweries, restaurants, and antique shops. Rest and recharge while you enjoy the light-filled, open floor plan with a wood-burning fireplace, a kitchen with plenty of cabinet space, and full-sized appliances for cooking. Private patio and community pool access are located outside the unit.

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, 240 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, 171 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

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.

4.96 out of 5 average rating, 164 reviews

1 bedroom condo, hiking, breweries, wineries

Enjoy the mountains in the spring & summer enjoy hiking or a swim in the heapool! 1BR 1BA centrally located in Wintergreen 5 minute walk to Wintergreen resort Close to many hiking trails Enjoy the many breweries & wineries in the area Mountaintop Market is across the street 1 Bedroom 1 Bath & New queen sleeper sofa Stocked kitchen, cookware, spices & cooking oils Premium coffee & assorted tea Private furnished patio Wood burning fireplace, all you need for a quiet getaway

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, 144 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!

4.97 out of 5 average rating, 119 reviews

Mountaintop Overlook: Warm Fires • Golden Views

Breathe in the Crisp Air, Cozy Up by the Fire, Take in Golden Views. The Mountain Top Overlook @ Wintergreen Resort is a cozy and clean two bedroom(king size beds), two full bathroom condo with a living room sleeper sofa. This condo accommodates 6 guests. It boasts panoramic window views of the Blue Ridge Mountains, while being located in sought after Wintergreen Resort. Ground level with easy access off the deck to a grassy area overlooking the valley.

A living room features large windows showcasing a vibrant sunset over the mountains. A cozy sofa is set against the backdrop, complemented by a patterned throw pillow. A coffee table with various decor items is positioned in front of it, alongside a decorative table with plants.

4.98 out of 5 average rating, 128 reviews

Slope side+Panoramic Mountain Views!

Panoramic views over Diamond Hill Ski Slope and the Blue Ridge Mountains. 2 bedroom/2 bath condo. Walk to slopes, hiking trails, and restaurants. Master w/King bed and attached bath with jetted tub. 2nd bedroom hosts 2 bunks- Twins over Double beds. Hall bath with shower and tub. Living Room with sleeper sofa, TV, and wood burning fireplace, wood included! Gated parking lot. Breathtaking Mountain Views + walking distance to the Mountain Inn! Perfection!

Popular amenities for Wintergreen Resort condo rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

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, 68 reviews

Fireworks & Mountain Views Ski In/Out Studio in WG

A comfortable living room features a cozy couch adorned with throw pillows, situated near a sleek fireplace. A round, woven coffee table stands in the center, while minimalist wall art and a reflective mirror enhance the clean, modern aesthetic.

5 out of 5 average rating, 22 reviews

Retreat @ 3 Ridges | 3 min walk to Slopes/Dining

An outdoor deck features a comfortable seating area with plush cushions and a coffee table. Two glasses of wine rest atop the table, surrounded by panoramic views of the Blue Ridge Mountains bathed in soft hues of sunset.

5 out of 5 average rating, 48 reviews

Buena Vista Panoramic Retreat: Million Dollar View

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, 63 reviews

Sitting on the 18th fairway

A cozy living room features a comfortable seating arrangement with plush chairs and a sofa. Large windows allow natural light to fill the space, enhancing the view of the surrounding greenery. A coffee table is placed centrally, surrounded by decorative plants.

4.79 out of 5 average rating, 73 reviews

Wintergreen Best location,Arcades,king bed,2 room

A patio area features a round table surrounded by four metal chairs, offering a clear view of the expansive landscape. The sky displays vibrant hues of orange and pink as the sun sets over the distant mountains, creating a serene backdrop.

4.98 out of 5 average rating, 41 reviews

Breathtaking Views from The Ledges

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.

5 out of 5 average rating, 38 reviews

Spacious Ski In Ski Out Condo with Mountain View

The main living area features a new sectional sofa facing a stone fireplace with a mounted TV above. A coffee table is positioned centrally, while light fills the room through large windows. The space is designed with soft carpeting and built-in shelving.

4.97 out of 5 average rating, 88 reviews

Beautiful Mountain Getaway - Walk to Everything!

Pet-friendly condo rentals

An inviting living space features a comfortable sectional sofa arranged around a round coffee table, complemented by a cozy rug. A gas fireplace is framed by white paneling, and large windows provide ample natural light while showcasing views of the surrounding landscape.

4.95 out of 5 average rating, 140 reviews

All-Season 2bd/2ba next to Spa view of Golf Course

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.

4.91 out of 5 average rating, 57 reviews

Wintergreen! Dog friendly, cozy and comfortable

A balcony view reveals a vast expanse of rolling green mountains under a clear blue sky. A square table is surrounded by two woven chairs, inviting guests to enjoy the serene landscape of the Blue Ridge Mountains and Rockfish Valley.

4.94 out of 5 average rating, 17 reviews

Condo with Valley Views!

The living area features comfortable leather seating arranged around a wooden coffee table. A fireplace is visible, surrounded by a stone accent, and large windows allow natural light to fill the space, offering views of the outdoors.

4.89 out of 5 average rating, 117 reviews

1720 High Ridge at Wintergreen Resort

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.

4.96 out of 5 average rating, 27 reviews

Recently updated - views of the Blue Ridge Mtns

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.

4.91 out of 5 average rating, 194 reviews

Tips Up: Cozy Slopeside Retreat w/ Fireplace

The living area features a spacious gray sectional couch with decorative pillows, a low wooden coffee table, and a patterned area rug. A wood-burning fireplace is situated against a white wall adorned with rustic decor. Natural light enters through large windows.

4.94 out of 5 average rating, 258 reviews

Cozy, clean, quiet mountain condo- King bed

4.93 out of 5 average rating, 75 reviews

Aspen Inspired + Walkout Deck & Top Views

Condo rentals with a pool

The exterior of the mountain condo is displayed, featuring a brown wooden structure with a steeply pitched roof. A wooden walkway leads to the entrance, bordered by low greenery. Large windows adorn the upper level, providing natural light. The setting is surrounded by trees, indicating a tranquil environment.

4.94 out of 5 average rating, 34 reviews

Pepper's Mountain Pad

A spacious living area is furnished with a comfortable couch adorned with multiple pillows. A wooden coffee table sits on a textured rug, complemented by a small side table with a plant. Bright light emanates from a floor lamp, while a ceiling fan provides air circulation.

4.9 out of 5 average rating, 119 reviews

Blue Ridge Retreat: Your Cozy Mountain Getaway

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.

4.9 out of 5 average rating, 50 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.

4.88 out of 5 average rating, 34 reviews

On the mountain, pet and child friendly

4.92 out of 5 average rating, 71 reviews

The living room features a spacious sectional sofa and two armchairs, arranged around a wooden coffee table. A wood-burning fireplace is located against a green wall, complemented by softly illuminated shelves. Natural light filters through windows, creating a cozy atmosphere.

Condo in Roseland

Nature’s Haven 1 Bedroom Condo Wintergreen Resort

4.99 out of 5 average rating, 79 reviews

Time To Get Away-Cozy Condo for 2 to 4

4.85 out of 5 average rating, 151 reviews

Ski-in/out Birds Eye View Fireplace DogOK King Bed

The family room features a spacious, comfortable sofa arranged around a round wooden coffee table. Large windows allow natural light to fill the space, with views of the outdoors. A stack of firewood sits neatly beside the fireplace, and dining space is visible in the background.