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.

4.91 out of 5 average rating, 189 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.

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, 322 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.

Superhost

The spacious lower living area features comfortable seating arranged around a central coffee table. A fireplace is present, flanked by large windows overlooking the outdoor space. A flat-screen TV is situated on a stand, complemented by decorative plants and patterned area rugs.

4.9 out of 5 average rating, 107 reviews

An All Season Resort- Serenity Above the Clouds

Spend your days skiing the best ski area in the region! Also enjoy hiking the area’s 30+ miles of trails, completing the highly rated ninja warrior course, soaring down a zip line at ~40mph, tubing down a hill longer than 3 football fields and/or aqua cycling in the lake! Whatever you decide, we’re certain you and your friends/family will enjoy fun-filled days. Book today & enjoy a newly decorated top floor, 2 level end unit with a warm cup of coffee/tea experiencing top-rated sunrise views!

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, 121 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, 111 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 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, 166 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 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.

4.94 out of 5 average rating, 159 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!

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, 254 reviews

Sunset Vista Mountain Views “Skies for Miles”

Welcome to Sunset Vista Villa, where you enjoy, “Skies for Miles.” This beautiful, 2 bedroom, 2 bath, first-floor-unit with second 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 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, 159 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

4.97 out of 5 average rating, 118 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 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, 188 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.

A cozy living area features soft sofas arranged around a wooden coffee table. A stone fireplace occupies one wall, with a fire burning brightly. Large windows provide natural light and a view of the surrounding landscape.

4.86 out of 5 average rating, 118 reviews

Fall mountain get away at Wintergreen!

You don’t want to miss these views! Come enjoy the breathtaking fall foliage in cozy comfort. Our 2 bedroom condo offers central access to dozens of wineries, breweries, and restaurants as well as being in short driving distance to Charlottesville and Shenandoah national park! Miles of available hikes await for you in the resort or venture further out to explore the mountain and waterfalls nearby!

Popular amenities for Wintergreen Resort condo rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

4.89 out of 5 average rating, 28 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 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, 55 reviews

Wintergreen! Dog friendly, cozy and comfortable

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, 45 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 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

The living room features two spacious gray sofas positioned around a wooden coffee table. A green area rug lays beneath, accentuating the cozy space. A flat-screen TV is mounted on the wall above a wooden shelf, with a fireplace nearby. Natural light enters through a window covered by blinds.

4.97 out of 5 average rating, 33 reviews

Wintergreen Condo -Steps to Ski

A sunset view is captured over the mountains, with the sun dipping below the horizon, casting warm hues across the sky. Dense trees frame the scene, providing a sense of tranquility amid the natural landscape.

4.94 out of 5 average rating, 35 reviews

Love of mountains oh fill my cup

A comfortable living area is presented, featuring a gray sectional sofa and an ottoman adorned with a decorative pattern. Natural light filters through multiple windows, illuminating the space. A small desk with two chairs is positioned nearby, with a fireplace adding to the cozy ambiance.

4.83 out of 5 average rating, 53 reviews

Happy hour on the 18th Hole

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, 138 reviews

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

Superhost

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.

4.91 out of 5 average rating, 32 reviews

On the mountain, pet and child friendly

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, 143 reviews

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

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, 238 reviews

Eight Minute Walk to Everything

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.

5 out of 5 average rating, 11 reviews

Condo with Valley Views!

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, 97 reviews

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

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, 114 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, 23 reviews

Recently updated - views of the Blue Ridge Mtns

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.

4.97 out of 5 average rating, 33 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, 118 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

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.

4.78 out of 5 average rating, 96 reviews

Cozy Condo - Sleeps 4

Pool Access: Scenic Condo in Wintergreen Resort!

A balcony view reveals a landscape of bare trees under a bright blue sky. Sunlight filters through the branches, illuminating the area. Two black outdoor chairs are positioned along the railing, inviting moments of relaxation amidst nature.

5 out of 5 average rating, 42 reviews

3BR condo steps from the slopes and Inn! King Bed!

4.91 out of 5 average rating, 68 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