Apartment vacation rentals in Wintergreen Resort

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Top-rated apartment rentals in Wintergreen Resort

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

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Top guest favorite
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, 105 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 favorite
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 favorite
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 favorite
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!

Top guest favorite
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 favorite
A wooden deck is elevated and features a vibrant red umbrella. Surrounding the deck are leafy green plants and a small seating area with pink chairs. A lattice design is present under the deck, adding texture to the space.
Apartment in Lovingston
4.9 out of 5 average rating, 147 reviews

Lovingston Get-Away Lovingston, VA

Guesthouse for ADULTS ONLY/ NO kids/pets located in Lovingston, VA. There are wineries, breweries, and distilleries. We have the Wintergreen Ski Resort. The Music Festival in October. Crabtree Falls and Humpback Rock for hiking. In Nelson Co., the Blue Ridge Parkway and Skyland Drive began. Nearby is UVa's Rotunda, Monticello, Appomattox, DC, Schuyler (the Waltons). Nelson hosts peach and apple festivals each year. The beautiful foliage to be seen in the fall and winter snowy mountains.

Superhost
A bright efficiency apartment is showcased, featuring a spacious bed with soft linens and decorative pillows. A small dining table with four chairs is positioned nearby, and a kitchenette with a microwave and coffee maker is visible. Light enters through two windows, enhancing the airy feel.
Apartment in Afton
4.87 out of 5 average rating, 359 reviews

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.

Top guest favorite
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, 209 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 favorite
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 favorite
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, 522 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.

Top guest favorite
Apartment in Wintergreen Resort
5 out of 5 average rating, 8 reviews

The highland hideaway

Welcome to our mountain retreat! Conveniently located near the Wintergarden Spa , the Nature foundation and numerous trails , our place is great to relax after skiing or to just be in the midst of nature or discover one of the many wineries and breweries nearby. 2 bedrooms : one with a queen bed and the second with a full bed . 2 bathrooms both with tubs . A fully equipped kitchen and a cozy living room with fireplace.

Guest favorite
A warm and cozy bedroom is visible, featuring a spacious bed with yellow pillows and a neutral quilt. A bedside table holds a ceramic cup and a small lamp with a textured shade. Soft lighting enhances the inviting atmosphere against wooden accents and a colorful area rug.
Apartment in Afton
4.78 out of 5 average rating, 102 reviews

Earth Room Suite | Quiet Blue Ridge Retreat

Find peace at Galleywinter Farm’s cozy farmhouse retreat in the Blue Ridge Mountains. Enjoy the entire private ground floor with its own entrance, rustic bathroom with Jacuzzi tub, and patio overlooking the woods. Guests love the calm, cozy energy—many say it’s the best sleep they’ve ever had. Relax in the sauna, forest bathing tub, or yoga studio and reconnect with nature in this healing, restorative space.

Popular amenities for Wintergreen Resort apartment rentals

When is the best time to visit Wintergreen Resort?

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Avg. priceﺩ.ﺇ573ﺩ.ﺇ580ﺩ.ﺇ485ﺩ.ﺇ477ﺩ.ﺇ488ﺩ.ﺇ514ﺩ.ﺇ514ﺩ.ﺇ496ﺩ.ﺇ510ﺩ.ﺇ474ﺩ.ﺇ481ﺩ.ﺇ602
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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 ﺩ.ﺇ331 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 & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Wi-Fi availability

    30 of Wintergreen Resort vacation rentals include wi-fi 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!

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