Apartment vacation rentals in Wintergreen Resort

Find and book unique apartments on Airbnb

Quick stats about apartment rentals in Wintergreen Resort

  • Total vacation rentals

    Explore 40 vacation rentals in Wintergreen Resort

  • Nightly prices starting at

    Wintergreen Resort vacation rentals start at ﺩ.ﺇ 294 per night before taxes and fees

  • Verified guest reviews

    Over 1,850 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    40 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!

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, 123 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, 529 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, 190 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
4.85 out of 5 average rating, 103 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 favorite
Apartment in Roseland
4.91 out of 5 average rating, 94 reviews

Dogwood Haven

Our haven is located in the Blue Ridge Mountains at Wintergreen Resort, a premier 4 seasons resort. It's a small quiet place in a great location. If your looking to pamper yourself, relax, explore, go on an adventure, try something new, or just enjoy the view Dogwood Haven is the place for you. Just within 3 miles you can: hike, bike, swim, ski, rock climb, play golf/tennis, shop, mini golf, and more. The areas surrounding the resort are rich with history, beauty, craft beer, wine, and fun.

Guest favorite
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
4.77 out of 5 average rating, 882 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 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, 227 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.

Guest favorite
Apartment in Wintergreen Resort
4.92 out of 5 average rating, 13 reviews

Amazing Views! Wintergreen Ground Level Condo

New Listing! Welcome to Vista Haus, a cozy 1BR / 1BA condo in the Cliffs condos at Wintergreen. The Cliffs are known for their amazing views overlooking the Blue Ridge Mountains and the ski slopes. Soak in the sunrise view from the living room, bedroom, or patio. The kitchen is fully stocked, and the unit is on the ground level, allowing for easy access in and out. Walk your dog directly out the back door! Managed by Chris at New School Hosting- click my profile for more reviews.

Top guest favorite
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
4.98 out of 5 average rating, 45 reviews

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!

Superhost
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, 109 reviews

Earth Room Suite | Peaceful 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. See our other listings - Galleywinter Farm on Linktree

Guest favorite
A modern kitchen is equipped with stainless steel appliances and a granite countertop. A pop of color is provided by a turquoise kettle and a 'HOME' sign above the cabinets. Soft lighting is cast from overhead fixtures, illuminating the workspace and creating a welcoming feel.
Apartment in Wintergreen Resort
4.93 out of 5 average rating, 121 reviews

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!

Guest favorite
The multi-story building is nestled among trees, featuring a set of wooden stairs leading to the entrance. Large windows are visible on each floor, allowing natural light to penetrate. A directory sign with multiple unit numbers is displayed at the base of the steps.
Apartment in Roseland
4.82 out of 5 average rating, 251 reviews

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

Popular amenities for Wintergreen Resort apartment rentals

When is the best time to visit Wintergreen Resort?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 760ﺩ.ﺇ 701ﺩ.ﺇ 635ﺩ.ﺇ 477ﺩ.ﺇ 488ﺩ.ﺇ 514ﺩ.ﺇ 514ﺩ.ﺇ 496ﺩ.ﺇ 510ﺩ.ﺇ 551ﺩ.ﺇ 529ﺩ.ﺇ 624
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Destinations to explore