Apartment holiday 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, 117 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!

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, 184 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.

A bright living area is highlighted by a sunny yellow couch, positioned next to a cozy dining space. A small round table is accompanied by four sleek chairs. Natural light fills the room through large windows, while a decorative rug adds warmth to the wooden floor.

4.96 out of 5 average rating, 242 reviews

Bee & Key—Staunton downtown

Staunton (pronounced “Stanton”) is one of the most vibrant, charming small towns you’ll find anywhere, and Bee & Key is in the center of it. This bright and stylish apartment is on the second floor of a grand 1885 home on East Beverley St. You will be half a block from the restaurants and shops of our bustling downtown, including Blackfriar’s Playhouse, the Woodrow Wilson Museum, The Shack restaurant, and Mary Baldwin University. We’re an easy walk from Staunton’s historic Amtrak station.

A welcoming entryway is presented with floral wallpaper and green wainscoting. A small armchair, paired with a decorative lamp and side table, creates a cozy reading nook. Artwork is hung on the walls, and a door leading to the outside is visible at the end of the hallway.

5 out of 5 average rating, 206 reviews

Queen City Hideaway

Imagine waking up to stunning mountain views, brewing coffee on your private deck, and planning your day exploring Staunton's vibrant downtown. Fully stocked! Need for nothing! Unwind in the heart of Staunton's historic charm! Sip coffee on your private deck overlooking Staunton's vibrant cityscape and rolling mountains. Binge your favorite show on our smart TV, and whip up a meal in the stocked kitchen. Walk to restaurants, shops, or the theater. Book your stay today and start planning!

4.89 out of 5 average rating, 152 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.

Flat in Lovingston

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.

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.

4.86 out of 5 average rating, 370 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.

4.98 out of 5 average rating, 219 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.

Flat 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.

4.99 out of 5 average rating, 536 reviews

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.

Flat in Crozet

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.

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.

4.79 out of 5 average rating, 105 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.

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.

4.94 out of 5 average rating, 112 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!

The exterior of The Storefront is displayed, showcasing a two-story, blue-painted building flanked by red brick structures. A striped awning is positioned over the entrance, and large windows provide a glimpse into the welcoming ambiance inside.

4.94 out of 5 average rating, 267 reviews

The Storefront: Downtown Staunton + Unique Stay

Welcome to The Storefront: A Very Small Hotel. The Storefront is located right in the heart of downtown Staunton. The Storefront was built in the early 1900's and was previously a tea shop before becoming a vacation destination. It's like having your own little townhouse in the heart of Staunton's historic district! Keep your car parked and walk everywhere you need to go.

4.82 out of 5 average rating, 248 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.

Flat 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

Popular amenities for Wintergreen Resort apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

5 out of 5 average rating, 3 reviews

The exterior of the garage apartment is visible, showcasing a rustic wooden facade and a metal roof. A gravel driveway leads to the structure, which features multiple doors and windows. Surrounding greenery includes trees, with a colorful seating area to the side.

Flat in Crozet

Sugar Hollow Outpost on the Moormans River

A spacious living area features a large leather sofa and an accent chair beside a floor lamp. Natural light filters through two windows, enhancing the neutral color palette. A patterned area rug covers the hardwood floor, complemented by a wall mirror and a simple chandelier.

4.92 out of 5 average rating, 25 reviews

Spacious Apartment. Short walk to downtown

The green exterior of a spacious house is surrounded by trees and gently rolling hills, showcasing a panoramic view of the Blue Ridge Mountains in the background. A well-maintained yard is visible, with landscaped gardens and a gravel driveway leading to the entrance.

Luxury Guest Quarters w/Blue Ridge Mountain Views

4.99 out of 5 average rating, 74 reviews

A spacious outdoor area features a seating arrangement with five wooden Adirondack chairs surrounding a circular fire pit. The open landscape showcases lush green grass and distant views of trees and rolling hills under a partly cloudy sky.

Flat in Charlottesville

Exquisite Views From Your Own Apartment

New place to stay

4-Season Mountain Escape | Ski, Golf, Wine

The suite features a stylish living area with a sectional sofa and armchairs. A dining table with upholstered chairs is visible, alongside a kitchenette equipped with modern appliances. A large smart TV is mounted on the wall, and natural light enters through a nearby window.

5 out of 5 average rating, 10 reviews

The Augusta Apartment at Historic Berkeley Place

A two-story building with a grey facade features large front windows adorned with white trim, showcasing displays inside. Blue shutters frame the windows, and a sign hangs from the front. The structure is situated on a charming downtown street with neighboring brick buildings.

5 out of 5 average rating, 292 reviews

The Downtown Corner Place - Location and Luxury

5 out of 5 average rating, 44 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.

Flat in Crozet

Mtn Vineyards Getaway

Private apartment rentals

A spacious living area features natural brick walls and wood beam ceilings. A sectional sofa is positioned beside a coffee table, with a rocking chair nearby. Large windows allow natural light, complemented by greenery from decorative plants. A vibrant Turkish rug adds color to the tiled floor.

4.96 out of 5 average rating, 165 reviews

The Hideaway Suite: Sauna & Lux Amenities

The cozy living area is furnished with a brown leather sofa and two armchairs. A glass coffee table sits on a soft rug, and artwork adorns the wall above the couch. Natural light enters through sliding doors, which lead to the outdoor area.

4.94 out of 5 average rating, 17 reviews

Weller’s Retreat at Stone Ridge

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, 44 reviews

Luxury Slope-View Condo w/ Sauna | Dogs OK

4.75 out of 5 average rating, 515 reviews

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.

Flat in Waynesboro

Spacious lower level Airbnb! READ SUMMARY!

A cozy bedroom features a king bed adorned with a colorful quilt and decorative pillows. A vintage-style chandelier hangs from the ceiling above. A patterned area rug covers the floor, and a charming fireplace is complemented by greenery and artistic decor. A television is mounted on the wall.

4.96 out of 5 average rating, 474 reviews

The Bohemian Suite: King Bed, Walk Downtown

A cozy living room features green walls and wooden flooring. A plush, dark green sofa sits alongside a brown accent chair. A glass coffee table occupies the center, while framed artwork adorns the walls. Natural light filters through the windows, complemented by decorative plants.

4.96 out of 5 average rating, 112 reviews

Downtown Luxe: Luxury Vintage + Downtown

A Gothic Revival Victorian home from 1877 is surrounded by lush greenery, featuring symmetrical hedges. The two-story house has a gray exterior with decorative rooflines and multiple gabled peaks, complemented by a broad set of steps leading toward the entrance.

4.97 out of 5 average rating, 267 reviews

Updated Victorian Welcomes You & Your Pets

The exterior of a historic two-story brick house is displayed, featuring white columns and large windows. Lush greenery and colorful flowers surround the front porch, which is complemented by a welcoming atmosphere created by its classic design. The house is set against a clear sky.

4.98 out of 5 average rating, 332 reviews

the apARTment on Church

Family-friendly apartment rentals

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.

4.93 out of 5 average rating, 45 reviews

Big Condo*Luxe Baths*Sweeping Views*Walk2Chairlift

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.

4.57 out of 5 average rating, 7 reviews

Snowbody Knows!

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.

Flat in Roseland

Wintergreen Resort Retreat Private Pool for Guests

5 out of 5 average rating, 3 reviews

Walk to ski! Updated condo w/ balcony & fireplace.

The exterior of the building displays a two-story structure with light brown siding and a front porch adorned with white railings. Windows are visible on both levels, complemented by a small garden and walkway leading up to the entrance.

4.93 out of 5 average rating, 161 reviews

Walker's dream. Close to downtown.

The historic mansion features a classic red-brick facade with white columns and large windows. Lush greenery and ornamental plants frame the entrance, highlighting the architectural details. A welcoming front porch invites guests to explore the property.

4.94 out of 5 average rating, 400 reviews

The Attic in Restored Mansion Walk everywhere!

4.91 out of 5 average rating, 22 reviews

A serene landscape showcases a lush green field bordered by dense trees. The scene features a mix of grassy areas and patches of bare earth under a bright blue sky with scattered clouds, evoking a sense of tranquility in nature.

Flat in Esmont

Farm Stay Basement Apartment

A vibrant sunset is captured over rolling hills, with shades of orange and pink filling the sky. A grassy field in the foreground leads to a white fence, and buildings are visible in the distance under a dramatic cloud formation.