Apartment holiday rentals in Wintergreen Resort

4.93 out of 5 average rating, 45 reviews

Big Condo*Luxe Baths*Sweeping Views*Walk2Chairlift

Step into our recently renovated sky-high condominium! Nestled on the Wintergreen ridge, we're a short distance from nature's wonders. Our unit strikes a balance between serenity and recreational opportunities. Whether you're skiing, hiking, or indulging in the local brew and wine scene, our place is the perfect hub. Cap off your adventures with the stunning 75-mile view from our balcony on clear days. Families with kids and couples seeking the best of Wintergreen's offerings are always welcome!

5 out of 5 average rating, 94 reviews

Endless Mountain Top Views from All The Way Up!

Our warm and inviting condo combines amazing proximity to hiking with to-die-for views of the Blue Ridge Mountains and the horizon 75 MILES distant! Our condo sits a mere 400-yd walk from the closest hiking trail and also has direct access to the ridge line walking area - perfect place for a morning stroll! This updated and modern mountain themed space features: ✸ Newly renovated! ✸ Stocked modern kitchen! ✸ Two full bathrooms! ✸ Helix Hospitality Mattresses!! ✸ Cozy Fireplace w/ wood provided!

5 out of 5 average rating, 12 reviews

3 Ridges 3 min walk to slopes,besides inn,King bed

Best of Wintergreen located in beautiful three ridges community, great location besides Wintergreen Inn, Parking in front of condo, short 3 min straight walk to the slopes , all in walking distance, enjoy garden ground level from your beautiful terrace, peacefull and private, Master bedroom with memory foam King Bed, Comfortable queen Sofa bed, granite kitchen, Central a/c cold and heat,hot water,wifi,TV with netflix,Keurig machine, regular coffee maker, Check in and out Time Flexible Please ask

Superhost

4.88 out of 5 average rating, 8 reviews

Eagles Court Ski In/Out Condo

Directly on the slope of Eagle's Swoop our condo is in a central location to everything in the Wintergreen Resort! Enjoy a true ski in/ski out experience with mountain views. Park your car in our designated parking spot and walk to The Market at Wintergreen, the Skyline Pavilion and The Edge & Coppermine restaurants that overlook the slopes. Enjoy 2 bedrooms with queen beds, 1 pullout sectional and 1 and 1/2 bathrooms. Get cozy in front of the wood burning fireplace & watch the skiers fly by.

4.98 out of 5 average rating, 170 reviews

Flat in Afton

Cozy stay with scenic views on a horse farmette

Cozy apartment with beautiful views on a horse farmette on the most scenic road in the county. Located within 15 miles from Charlottesville and only 6 miles from Shenandoah National Park and the Blue Ridge Parkway, this vacation rental is the perfect spot if you are looking for places to hike, scenic drives or visit the many wineries, breweries or cideries located in close proximity. The apartment is situated over the garage and has its own separate entrance offering guests plenty of privacy.

4.88 out of 5 average rating, 68 reviews

Wintergreen Getaway

Relax with the whole family at this peaceful place to stay. Enjoy morning coffee and evening cocktails on the deck fronting the golf course. You will love the location and features! Walking distance to spa, The Wintergreen Nature Foundation, and Fire & Frost. Convenient to slopes, Chestnut Springs pool and Upper Shamokin Falls. A great place to relax after a full day of hitting nearby slopes or hiking trails, and exploring Nelson 151's winery and brewery attractions. Stairs to access. WiFi!

4.94 out of 5 average rating, 83 reviews

Wintergreen Escape | King Bed + Porch Views

Escape to our four-season Wintergreen condo! ***The porch will be unavailable from 08/18/25 to 09/12/25 due to scheduled deck repairs! Enjoy crisp mountain air, scenic hikes, fall foliage, and nearby wineries and breweries. Walk to Discovery Ridge, the spa, and activities! Relax at the seasonal heated pool, play a round of golf, or explore the Blue Ridge Parkway and Shenandoah National Park. Perfect for couples or families, cook a cozy meal or unwind by the fire after a day outdoors!

4.87 out of 5 average rating, 355 reviews

Flat in Afton

Best Spot on the Wine/Brew Trail!

Charming, private, efficiency apartment located in the center of winery/brewery country! This efficiency offers fiber internet (super fast)! Less than a minute to Blue Mountain Brewery, Flying Fox Vineyard, and Valley Road Vineyard. Less than 5 minutes to Veritas Vineyard, Cardinal Point Vineyard, Silver Back Distillery, Afton Mountain Vineyards. 5-10 minutes to Bold Rock Cidery, Devils Backbone Brewery, Brewing Tree Brewery, Mountain Meadery, Hill Top Berry Farm, and so many more.

4.97 out of 5 average rating, 34 reviews

Luxury Condo: Stunning Slope Views, Sauna, Dogs-Ok

Welcome to the view from above the clouds! Our two-floor penthouse condo right on the ridge at Wintergreen Resort has stunning views of the mountains and ski slopes. On warm days, you can soak in the sun and dine al fresco on the enormous wraparound deck. On chilly nights, there’s a wood-burning fireplace for cozying up. And no matter the weather, you can soothe your muscles in the state-of-the-art infrared sauna. Whether you’re looking for peace or adventure, this is the place!

4.97 out of 5 average rating, 96 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.

4.98 out of 5 average rating, 198 reviews

Flat in Rockfish

Blue Ridge Bliss - For family & friends to enjoy!

Welcome to Blue Ridge Bliss! Come enjoy the mesmerizing mountain top views of this well-appointed condo in The Ledges of Wintergreen Resort. It’s the perfect place to unwind, unplug and recharge. Whether here to ski, hike, or visit Virginia wineries, cideries, or craft breweries you’re sure to enjoy the beautiful views from the living room and deck. A short walk to The Highlands lift and across the street from the dog park, and picnic area it’s an ideal location.