Apartment vacation rentals in Wintergreen Resort

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.

4.99 out of 5 average rating, 124 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!

FamilyLocationQuiet

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.

4.75 out of 5 average rating, 533 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.

FamilyValueAmenities

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.

4.98 out of 5 average rating, 193 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.

FamilyLocationOutdoor spaces

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.

4.85 out of 5 average rating, 109 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!

LocationValueIndoor spaces

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.

4.96 out of 5 average rating, 23 reviews

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

FamilyLocationIndoor spaces

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.

4.87 out of 5 average rating, 386 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.

FamilyLocationTV

4.98 out of 5 average rating, 229 reviews

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

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.

ValueFamilyView

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.

4.92 out of 5 average rating, 129 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!

FamilyLocationSleep quality

An outdoor deck is adorned with string lights, creating a warm ambiance. A seating area with a wooden table and lounge chairs is set against a backdrop of lush trees and mountains visible in the distance, inviting relaxation in a natural setting.

4.85 out of 5 average rating, 27 reviews

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*

LocationFamilyWifi

5 out of 5 average rating, 14 reviews

*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.

LocationFamilyCheck-in

4.82 out of 5 average rating, 252 reviews

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

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

ValueFamilyWifi

4.95 out of 5 average rating, 22 reviews

little mountain haven. True ski-in Ski out

Wake up to mountain views, falling snow, or rolling mist at Little Mountain Haven. Enjoy true ski-in/ski-out access with no shuttles or driving—just step out and hit the slopes. Every season brings beauty, from snowy winters to colorful fall. A cozy retreat where adventure and comfort meet.

LocationKitchenSkiing

Popular amenities for Wintergreen Resort apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

4.95 out of 5 average rating, 61 reviews

A craftsman-built apartment is nestled among lush greenery, surrounded by mountain forests. Vibrant flowers frame the foreground, leading to the wooden structure with a metal roof. The natural landscape features rolling hills and a clear blue sky, creating an inviting outdoor setting.

Apartment in Tyro

Crabtree Falls Mountain Hollow Guesthouse

FamilyLocationTV

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.

4.98 out of 5 average rating, 46 reviews

Ski Slope Views & Private Sauna | Dog Friendly

FamilyLocationHiking

4.88 out of 5 average rating, 77 reviews

The exterior view of a two-story condo showcases a blend of brown and white siding, with large windows allowing natural light to enter. A wooden deck with steps leads to the main entrance, surrounded by greenery and a gravel pathway.

Apartment in Roseland

Close to Activities/Shops/slopeside

LocationValueQuiet

4.97 out of 5 average rating, 31 reviews

Spacious 2BR Apartment w/ Pool & Fenced Yard

ValueFamilyAccuracy

A cozy living area features a neutral color palette with a comfortable sectional sofa and a second soft sofa. A wooden coffee table is centered between the seating. Artwork is displayed on the wall above the fireplace, complemented by decorative items on the mantel.

5 out of 5 average rating, 14 reviews

Cozy base camp for blue ridge adventures

ValueFamilyHospitality

4.94 out of 5 average rating, 16 reviews

Amazing Views! Wintergreen Ground Level Condo

ValueLocationPets

A scenic view showcases lush greenery with trees framing a winding pathway. The landscape features rolling hills in the background under a bright, partially cloudy sky, offering a tranquil atmosphere for outdoor exploration.

4.92 out of 5 average rating, 13 reviews

Fantastic views/FallFoliage/PupFriendly!

LocationFamilyNearby

Superhost

5 out of 5 average rating, 4 reviews

Ski-In/Ski-Out + Blue Ridge Views | Wintergreen

ValueBathroomCondition

Private apartment rentals

4.85 out of 5 average rating, 177 reviews

A cozy condo is partially visible behind snow-covered trees, with a deck and wooden railing leading to snow-blanketed steps. The scene is enhanced by gentle snowfall, creating a serene winter landscape.

Apartment in Roseland

Wintergreen Resort Retreat Private Pool for Guests

ValueLocationWalkability

A comfortable seating area is depicted, featuring a navy blue sofa adorned with bright orange and white pillows. A round coffee table sits atop a patterned area rug, while natural light streams through glass patio doors opposite. A leather armchair complements the inviting space.

4.98 out of 5 average rating, 51 reviews

The Rookery

FamilyLocationHiking

Superhost

A cozy family room is anchored by a stone fireplace with a glowing fire, complemented by wooden paneling. A mounted television and a cabinet with board games are positioned nearby. A floor lamp and stacked firewood add warmth and practicality to the space.

4.5 out of 5 average rating, 22 reviews

Ski In/Ski Out 3 BR Mountainside Condo!

LocationFamilySkiing

The living room features a spacious couch with colorful pillows, complemented by two accent chairs. A round coffee table sits on a patterned rug, and large windows provide ample natural light, offering views of the surrounding area.

4.94 out of 5 average rating, 64 reviews

Shenandoah Valley Atelier: NEW Waynesboro Loft

ValueFamilyCheck-in

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.

4.78 out of 5 average rating, 110 reviews

Earth Room Suite | Peaceful Blue Ridge Retreat

FamilyValueCheck-in

A cozy living area is present, featuring a spacious sectional sofa adorned with colorful throw pillows. A coffee table is positioned centrally, and a large flat-screen television is mounted on the wall. Natural light streams through expansive windows, highlighting the warm wood accents.

4.92 out of 5 average rating, 12 reviews

Slope-Side with a Mountain View

FamilyLocationHiking

4.92 out of 5 average rating, 13 reviews

Eagles Court Ski In/Out Condo

LocationHospitalityBathroom

Superhost

Apartment in Greenwood

New place to stay

Blue Ridge Apartment - Gateway to the Mountains

Family-friendly apartment rentals

4.89 out of 5 average rating, 156 reviews

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

Lovingston Get-Away Lovingston, VA

FamilyValueDecor

A living room features a comfortable blue sofa with an ottoman, complemented by two accent chairs. Decorative ski equipment and wooden snowshoes adorn the walls. A rustic wooden bookshelf is visible, while a cozy fireplace adds a warm focal point. Natural light filters through nearby curtains.

4.56 out of 5 average rating, 9 reviews

Snowbody Knows!

ValueLocationCheckout

5 out of 5 average rating, 3 reviews

Slopeside Condo Ski In Ski Out Diamond Hill

LocationComfortSleep quality

An open living and dining area is visible, featuring a comfortable gray sofa and a wooden dining table with multiple chairs. Light hardwood flooring extends throughout. A modern kitchen is partially seen in the background, with contemporary appliances and a small unobtrusive rug underfoot.

Apartment in Stuarts Draft

4.06 out of 5 average rating, 16 reviews

Sandstone Lodge

LocationValueCheck-in

5 out of 5 average rating, 51 reviews

A welcoming living space features a gray couch adorned with orange and decorative pillows. A wall-mounted TV is positioned above a faux fireplace, complemented by a glass coffee table. A green accent wall and a patterned rug add character to the area, with wooden shelves displaying various items.

Apartment in Crozet

Mtn Vineyards Getaway

ValueFamilyAccess

A comfortable living area features a light-colored, spacious sofa positioned against a softly lit wall. A small dining table with black chairs sits nearby, complemented by a kitchenette equipped with modern appliances. Soft carpeting covers the floor, adding to the inviting atmosphere.

4.75 out of 5 average rating, 8 reviews

Valley retreat

LocationCleanlinessNearby

4.61 out of 5 average rating, 33 reviews

Castle Abgar

ValueLocationHospitality

A living area features a light-colored sofa and a wooden dining table with four chairs. The space is accented by a fireplace and a large window allowing natural light. A decorative rug adds warmth to the room, and a television is mounted on the wall.