Apartment vacation rentals in Wintergreen Resort

Find and book unique apartments on Airbnb

Top-rated apartment rentals in Wintergreen Resort

Guests agree: these apartments are highly rated for location, cleanliness, and more.

%{current} / %{total}1 / 1
Top guest favourite
The living room features a spacious seating arrangement with two sofas, a cozy armchair, and a round coffee table. Large windows frame expansive views of the Blue Ridge Mountains, inviting natural light into the airy space. A dining table for six is visible in the background.
Apartment 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!

Top guest favourite
A balcony is featured, showcasing two Adirondack-style chairs positioned for optimal mountain views. Sunrise illuminates the expansive horizon, with soft light reflecting off the distant landscapes. The floor is made of wood, enhancing the outdoor ambiance.
Apartment in Wintergreen Resort
4.99 out of 5 average rating, 104 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!

Guest favourite
The exterior features a two-story home with a welcoming red front door. The entrance is accessible by a wooden staircase, surrounded by a deck and landscaped with trees and fallen leaves. A paved driveway accommodates parking for multiple vehicles.
Apartment in Waynesboro
4.75 out of 5 average rating, 510 reviews

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.

Top guest favourite
Rolling green fields are framed by colorful trees in autumn hues, creating a serene landscape. Horses are seen grazing near a small shelter, with distant hills providing a picturesque backdrop under a soft sky.
Apartment in Afton
4.98 out of 5 average rating, 177 reviews

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.

Guest favourite
The living area features a comfortable sectional sofa and a wooden coffee table, with a visible fireplace centrally located. Large windows provide natural light and views of the outdoor space. A mounted television is positioned above the fireplace, complementing the cozy ambiance.
Apartment in Wintergreen Resort
4.86 out of 5 average rating, 79 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!

Guest favourite
A spacious studio features a queen-sized bed with crisp white linens and decorative blue pillows. Natural light filters through sheer curtains, illuminating the room. A small artwork in blue hangs above the bed, complemented by bedside lamps. A minimalist table is positioned at the foot of the bed.
Apartment in Afton
4.78 out of 5 average rating, 855 reviews

Studio Apt. in Wine/Brewery Country/on 151

Clean & bright studio apartment with full kitchen & full bath. Less than 1 mile from Blue Mt. Brewery and Flying Fox Vineyard. Cardinal Point Vineyard, Afton Mountain Vineyard, Silverback Distillery, Valley Road Vineyard & Veritas Vineyard all between 2-5 miles away. Right on 151 also known as "alcohol alley". Tons of breweries, distilleries, ciderys & vineyards all up and down the road. The setting is peaceful. Apt. has fiber internet and Apple TV. Pets welcome for 30 dollars per pet.

Top guest favourite
A panoramic view of rolling mountains is displayed under a colorful sky during sunrise. Soft clouds hover over the lush green hills, creating a serene landscape. The vast expanse of nature invites tranquility and offers a sense of openness.
Apartment in Wintergreen Resort
5 out of 5 average rating, 12 reviews

Family and dog friendly with views and 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

Top guest favourite
A bright and airy living area is highlighted by large windows offering mountain views. A casual seating arrangement features a light-colored sofa and a wooden dining table surrounded by black chairs. Sliding glass doors provide access to an outdoor deck.
Apartment in Rockfish
4.98 out of 5 average rating, 208 reviews

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.

Top guest favourite
An outdoor dining setup on a spacious deck features several plates with a breakfast spread, including eggs, fruit, and pastries. A steaming cup and a glass of juice are present. In the background, a telescope is positioned to enjoy the scenic mountain view under a cloudy sky.
Apartment in Wintergreen Resort
4.97 out of 5 average rating, 38 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!

Top guest favourite
A table set for two features a bottle of sparkling beverage and two glasses, accompanied by an elegant plate of appetizers. The backdrop showcases expansive mountain views under a bright sky, enhancing the serene atmosphere of the outdoor dining area.
Apartment in Wintergreen Resort
4.97 out of 5 average rating, 106 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.

Top guest favourite
The exterior of a bright red barn-style building is showcased, featuring large windows that allow natural light to enter. A well-maintained lawn with small shrubs enhances the landscaping, while a staircase leads up to the entrance. The inviting setting is complemented by a clear blue sky.
Apartment in Crozet
4.99 out of 5 average rating, 521 reviews

The Barn at Haden near Wineries and C'ville

The Barn at Haden is a custom well appointed finished 2 bedroom, 1 full bath space elevated above a detached 3 car garage with a large outdoor private deck. It features a fully equipped gourmet kitchen with high end finishes. Whether staying for a night or for the weekend, it is an experience to enjoy the easy living Crozet has to offer. Walkable/bikeable to downtown Crozet, 2 miles to King Family Vineyard & Chiles Peach Orchard and 15 minutes from Charlottesville.

Guest favourite
A spacious living area features a dark brown sofa adorned with yellow pillows, alongside a stylish coffee table. A flat-screen TV is mounted on the wall, and natural light brightens the space. The open layout connects to a modern kitchen in the background.
Apartment in Afton
5 out of 5 average rating, 8 reviews

The Meadows of White Mountain

A newly finished space with all of the amenities and stylish attributes to have a peaceful and comfortable home away from home. The Meadows of White Mountain sit nestled into the hillside and is central to the areas many attractions. A quiet and private property. The Meadows is comfy and secluded, and in the winter months when the trees are bare the view opens up to the beautiful western mountain range. We look forward to sharing this wonderful space with you!

Popular amenities for Wintergreen Resort apartment rentals

When is the best time to visit Wintergreen Resort?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$220 CAD$223 CAD$186 CAD$183 CAD$187 CAD$197 CAD$197 CAD$190 CAD$196 CAD$182 CAD$185 CAD$231 CAD
Avg. temp2 °C4 °C8 °C14 °C18 °C22 °C24 °C23 °C20 °C14 °C9 °C4 °C

Quick stats about apartment rentals in Wintergreen Resort

  • Total vacation rentals

    Explore 30 vacation rentals in Wintergreen Resort

  • Nightly prices starting at

    Wintergreen Resort vacation rentals start at $127 CAD per night before taxes and fees

  • Verified guest reviews

    Over 1,540 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Wifi availability

    30 of Wintergreen Resort vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Wintergreen Resort rentals

  • 4.9 Average rating

    Wintergreen Resort stays are highly rated by guests—averaging 4.9 out of 5!

Destinations to explore