Condo vacation rentals in Wintergreen Resort

4.96 out of 5 average rating, 291 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.

An aerial view showcases a lively outdoor gathering space surrounded by greenery. The layout features a spacious lawn with people sitting at tables under wooden awnings. A large building is visible in the background, along with a parking area filled with vehicles.

4.93 out of 5 average rating, 152 reviews

Cozy Updated Wintergreen Condo at Devil’s Knob

This 2 bedroom, 2 bathroom, fully updated condo is a great place to spend your get away at Wintergreen. Fantastic wifi throughout. Brand new queen mattress in master bedroom. Enjoy Apple TVs in the living room and bedrooms. Sony 55” tv with soundbar and subwoofer in living room. Mounted big screen tv in the master bedroom. NES classic and Nintendo Switch dock. On the deck is a Weber electric grill. Nest thermostat. We hope you will enjoy this fully loaded home away from home as much as we do!!

Two chairs are positioned near a large panoramic window, offering expansive views of the Blue Ridge Mountains. A small table sits between the chairs, adding a touch of convenience to the inviting corner. Soft light filters through the sheer window treatments.

4.97 out of 5 average rating, 119 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 image captures a panoramic view of rolling mountains blanketed in lush greenery, under a serene twilight sky transitioning from soft blues to warm pink hues. The expansive landscape conveys a sense of tranquility and connection to nature.

4.94 out of 5 average rating, 217 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.

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.

4.98 out of 5 average rating, 133 reviews

2-min drive from hiking/resort, stairs-free

Peaceful, newly renovated mountain-top retreat. Relax or work from home. End your day with a hike or personal spa treatment before you linger with a glass of wine over an amazing view at sunset. It’s 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 pools CLOSED

Superhost

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.

4.85 out of 5 average rating, 105 reviews

Wintergreen Cozy Mountain Getaway!

Take advantage of the best snow conditions this area has seen in years! Come stay in our cozy mountain condo and experience the skiing and snowboarding you’ve been looking for! Enjoy the crisp mountain air while relaxing on the patio, treat yourself at the Spa at Wintergreen that is within walking distance, or explore nature’s winter beauty by hiking (carefully!) through nearly 30 miles of trails winding throughout the resort. Our condo is located less than a mile from the main resort.

A panoramic view of the mountainous landscape showcases layers of rolling hills and valleys, bordered by a mix of lush greenery and rocky outcrops. The sky is partially cloudy, with soft light illuminating the scenery below.

4.94 out of 5 average rating, 226 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, 158 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

An outdoor patio area is highlighted by a sturdy picnic table set on a stone surface, with a slight dusting of snow. Wooden supports frame the space beneath a balcony, which overlooks the patio and surrounding area.

4.9 out of 5 average rating, 134 reviews

All season 3bd/3ba ski out/in - Location & Views!

Spend your days hiking the area’s 30+ miles of trails, completing the ninja warrior course, soaring down a zip line at ~40mph, tubing down a hill longer than 3 football fields, playing volleyball/kayaking in the lake or ski out/ski in the patio door to the best ski area in the region! Bring your friends/family to enjoy special home away from home! Book today & enjoy our two-level, two fireplaces, 3 bathroom unit with a warm cup of coffee/tea experiencing top-rated views! Dog friendly!

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, 132 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!

4.96 out of 5 average rating, 128 reviews

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

Come experience four seasons of fun- hit the ski slopes, hike the blue ridge mountains, enjoy local cider or beer, or cozy up by the fire and enjoy the mountain views. Located across the street from the aquatic/fitness center & spa, on the Devil's Knob golf course, and next to the ski shuttle pickup location and Nature Foundation, the location couldn't be better. The unit has a spectacular sunset view from the balcony, a gas fireplace, and speedy wifi for working or streaming!

A clean, inviting swimming pool is surrounded by lush greenery and tall trees. Comfortable lounge chairs are positioned nearby, and sunlight reflects off the water, creating a serene atmosphere. The pool area is enclosed with a wooden railing for safety.