Apartment holiday rentals in Wintergreen Resort

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!

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.

Spacious lower level Airbnb! READ SUMMARY!

Hello everyone! I’m not going to try to convince you to stay at this Airbnb but instead address the issues that guests have complained about in reviews. This listing is priced accurately and cheap because there isn’t much besides 2 king beds, bathroom, washer/dryer. There is a bit of noise from upstairs when people walk around but usually no later than 11 PM. Please keep in mind when reviewing that you’re not paying very much to stay here. If you’re going to complain, please stay elsewhere.

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!

Panoramic Blue Ridge Views | dog friendly | pools!

2 bed/2 full bath renovated condo at the Overlook! Dog friendly! This beautifully renovated condo is appointed with 1 king bed, 1 queen bed and an olympic queen sized sleeper sofa + pack-n-play - it is ideal escape for a couples getaway or a family vacation! Enjoy a great view of the fireworks from the balcony to ring in the New Year or to celebrate our Independence Day. There are legos, magnatiles, children’s books and a rotating assortment of other kids toys to keep kids entertained

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.

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 Fire & Frost eatery and the Wintergreen Spa, this is an ideal location.

Ski Slope Views & Private Sauna | Dog Friendly

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!

Wintergreen Escape | King Bed + Porch Views

Escape to our four-season Wintergreen condo! 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!

Walk to Everything -Mtn View at Swoopside Hideaway

Stay at the heart of Wintergreen Resort at Swoopside Hideaway, a wonderful 2BR, 1.5BA condo perched right on the Eagles Swoop slope. Our prime location is steps from The Market, The Mountain Inn, hiking, ski lifts, shops, and restaurants. If you’re someone who doesn’t like to park and drive for everything, this is your ticket for a stress free mountain adventure. *Newly renovated in 2025*

*NEW* Fully Renovated Slopeside Condo

New listing! Enjoy stunning views and easy slope access in this beautifully renovated, 2 bedroom Diamond Hill condo. Located directly on the family-friendly slopes, you'll have a front row view of all the skiing and snowboarding action. This condo is extremely comfortable & relaxing and is a short 8-10 minute walk to the Mountain Inn Village with restaurants, activities, market and shops.

Spacious 2 bedroom, 2 bath condo w/ full kitchen

2 bedrooms, 2 full bathrooms with kitchen and living room. Also features a private outside patio overlooking the golf course. Located on top of Wintergreen resort. Access to unlimited hiking trails, ski/snowboarding seasonally, and very short drive to all the winery's and breweries in Nelson county