Airbnb your place

Places to stay near Wintergreen Resort

Book unique holiday rentals, homes and more on Airbnb

Top-rated holiday rentals near Wintergreen Resort

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

%{current} / %{total}1 / 1
Top guest favourite
A welcoming living area features two leather couches arranged around a wooden coffee table, which is complemented by a patterned rug. Large windows allow natural light to illuminate the space, offering views of the surrounding trees. Sliding glass doors provide access to an outdoor deck.
Home in Wintergreen Resort
4.99 out of 5 average rating, 140 reviews

Close to skiing! | King Beds | Fireplace | Hot Tub

Welcome to Blackrock Escape! Dog friendly, 2BR/2.5BA mountain home in prime location at Wintergreen Resort. 3-min drive to the Mountain Inn. Walk to hiking trails–the Plunge Trail/Blackrock Park is only a 2-min walk. Two BRs on first floor - both with King-size Helix mattresses, smart TVs, and en suite bathrooms. Wood burning fireplace, games, puzzles, 65” smart TV in living room. Two decks w/gas grill and hot tub. Keurig K-Duo coffee maker and dishwasher in kitchen. Full-sized washer and dryer.

Top guest favourite
A cozy cottage, named the 'Sugah Shack,' is nestled amidst the rolling hills of the Blue Ridge Mountains. The white exterior contrasts with the vibrant greenery surrounding the property, while the majestic mountains form a picturesque backdrop against a bright, partly cloudy sky.
Cottage in Afton
5 out of 5 average rating, 211 reviews

Cozy Mountain Cottage on Brew/Wine Trail-King Bed

Welcome to the Sugah Shack, a cozy, beautifully appointed new construction cottage nestled in the foothills of the Blue Ridge Mountains! Located midway on the Brew Ridge Trail, but 500 yards off the byway, so guests have a quiet retreat. Perfect for romantic getaways, destination telework space, or families exploring this outdoor paradise community. Stunning property boasts beautiful vistas with sweeping 300-degree mountain and a year-round calendar of outdoor activities. GAS FIREPLACE/FIREPIT

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.
Flat in Wintergreen Resort
4.99 out of 5 average rating, 103 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!

Top guest favourite
The gravel pathway leads to a charming log cabin, framed by tall trees and surrounded by greenery. A sign reading 'COZY MOUNTAIN CABIN' is positioned near the path, inviting visitors to explore this secluded retreat in the Blue Ridge.
Cabin in Roseland
4.96 out of 5 average rating, 732 reviews

Cozy Mountain Cabin

Snuggled in the Blue Ridge. Secluded from the crowds. Experience your visit in an authentic log cabin. Spacious sleeping loft. Perfect romantic escape, friends getaway, or personal retreat. Workout area/sitting room. Fresh eggs (in season), wine, tea, coffee. 1G Internet, SMART TV. A/C. Less than 2 miles to Devil's Backbone and Bold Rock. Minutes from App. Trail, Wintergreen Resort, breweries, wineries, cideries, restaurants, horseback riding, hiking trails, outdoor concerts, & antique shopping.

Top guest favourite
The two-story condo features a warm wood exterior, framed by lush greenery and trees. Wide wooden steps lead to the entrance, giving access to individual balconies that enhance the inviting appearance of the building.
Apartment in Wintergreen Resort
4.95 out of 5 average rating, 327 reviews

Five Minute Walk to Everything!

**Pet friendly** two bedroom, two bath, loft style condo centrally located at Wintergreen Resort. Ski check-in, restaurants, the mountaintop provisions market, and the Mountain Inn and conference center are all within a 5 minute walk! This is a two-story unit with loft style master bedroom and en suite bath, and first floor bedroom with hall bath. Parking, pool access, washer/dryer, and Wi-Fi included. Fully stocked kitchen, wood burning fireplace, balcony, all towels/linens provided. Sleeps 5.

Top guest favourite
The living area features large sliding glass doors that open to a stunning view of the mountains. A modern dining table is positioned nearby, illuminated by a pendant light. Comfortable seating is arranged around the room, enhancing the inviting atmosphere.
Apartment in Wintergreen Resort
4.97 out of 5 average rating, 114 reviews

Luxury Condo in the Sky! Finest in Wintergreen!

Welcome to our recently renovated luxury condo in the sky! Perched on the edge of the Wintergreen ridgeline, we are just a stone’s throw from nature’s bounty. Our condo offers the perfect blend of relaxation and access to recreation. Hit the ski slopes, take a hike, or explore the bountiful brew and wine scene and then come enjoy the view. The horizon is 75 miles distant from our balcony on a clear day! We love hosting families with kids or couples coming to enjoy all that Wintergreen offers!

Guest favourite
The interior of the tiny house features an open kitchen layout with modern appliances and a central island. A geometric area rug extends across the floor, while light wood accents create a warm feel. Shelving holds books and decor, enhancing the cozy atmosphere.
Cabin in Nellysford
4.96 out of 5 average rating, 236 reviews

Tiny Luxury Retreat: Lake, Hikes, Brews & Vines

Welcome to our luxurious tiny house nestled in the heart of Nelson County, Virginia. This enchanting retreat, surrounded by the majestic Blue Ridge Mountains, offers an unparalleled experience in a landscape dotted with wineries, breweries, distilleries, and sprawling farmland. This luxury tiny house was built in 2022 and is available for couples, solo travelers, or a small family wanting to explore this beautiful stretch of the Blue Ridge Mountains. FREE Electric Vehicle Charger on-site.

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.
Flat 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
Home in Wintergreen Resort
4.96 out of 5 average rating, 113 reviews

Cliffs Edge- It's Pumpkin Spice Time!

An open floor plan with high ceilings and large skylights, this amazingly engineered home will stun you with its incredible mountain views! This spacious home, with its cantilevered decks, makes this perfect for any family. The large upstairs loft, adjacent to the upstairs bedrooms, offers movies, games, puzzles, and comfortable seating. Wi-Fi, Netflix, and Samsung Smart hub give plenty of entertainment options. The spacious living area and dining room have abundant seating for all.

Top guest favourite
A private balcony features wooden railings, with a light dusting of snow on the ledge. Lush pine trees stand prominently in the background, contrasting against a clear blue sky and hints of distant landscape, contributing to a serene outdoor viewing experience.
Apartment in Wintergreen Resort
4.97 out of 5 average rating, 155 reviews

2-min drive from slopes, stair-free/free firewood!

Peaceful, recently renovated mountain-top retreat. Relax or work from home. End your day with a hike or spa treatment around the corner—linger with a glass of wine at sunset. It’s all only a 2 minute walk from the front door. Welcome to our mountain home! 2-3 min drive from ski lifts/resort, hiking Free firewood (seasonal) Family games & smart TVs (no cable) for movie night (must sign into your own subscriptions) Smartlock entry Stair-free entry *outdoor HOA pools CLOSEDe

Guest favourite
A private furnished patio features a cozy seating area with light-colored cushions on a dark frame sofa. A wooden coffee table sits in front, accented by a woven rug. The surrounding greenery adds a natural backdrop, creating a peaceful setting for relaxation.
Apartment in Wintergreen Resort
4.96 out of 5 average rating, 164 reviews

1 bedroom condo, hiking, breweries, wineries

Enjoy the mountains in the spring & summer enjoy hiking or a swim in the heapool! 1BR 1BA centrally located in Wintergreen 5 minute walk to Wintergreen resort Close to many hiking trails Enjoy the many breweries & wineries in the area Mountaintop Market is across the street 1 Bedroom 1 Bath & New queen sleeper sofa Stocked kitchen, cookware, spices & cooking oils Premium coffee & assorted tea Private furnished patio Wood burning fireplace, all you need for a quiet getaway

Top guest favourite
The cabin exterior features a spacious wrap-around porch with a national flag gently waving. The structure combines stone and wood elements, set against a backdrop of tall trees and fallen leaves, presenting a private and serene atmosphere.
Cabin in Vesuvius
4.99 out of 5 average rating, 361 reviews

The Sanctuary

Nature lovers paradise! Named "The Sanctuary" for the place you can UNPLUG, unwind & find your peace! Perched up high on nearly 60 acres- you are sure to get fresh air & the rest you are searching for! Only 4 miles to Wintergreen, 6 miles to Sherando lake and backs up to the Blue Ridge Parkway there are plenty of things to do OR just relax and enjoy the crickets & stars! With crazy careers, growing kids & constant hustle- everyone needs a hide out like this every now and then!

Popular amenities for holiday rentals near Wintergreen Resort

KitchenWifiPoolFree parking on premisesAir conditioning

Apartment rentals with wifi

Guest favourite
A spacious living area features a wood-burning fireplace surrounded by light-colored walls. A comfortable couch, adorned with a welcoming throw pillow, faces a wooden coffee table. Natural light enters through large windows, offering views of the outdoor greenery.
Apartment in Wintergreen Resort
4.93 out of 5 average rating, 239 reviews

The Modern Mountain Condo

Top guest favourite
A cozy living room is presented, featuring two plush leather sofas, a coffee table, and a fireplace. Natural light enters through large windows, and decorative accents enhance the warm ambiance. A flat-screen TV sits on a stand, completing the inviting space.
Apartment in Wintergreen Resort
4.98 out of 5 average rating, 192 reviews

Cozy getaway with heated floors

Top guest favourite
The exterior of a two-story cabin houses warm wooden accents and large windows. The entrance features a welcoming set of wooden steps leading up to a balcony, surrounded by tall trees, with a concrete pathway leading toward it.
Apartment in Wintergreen Resort
4.94 out of 5 average rating, 240 reviews

Eight Minute Walk to Everything

Guest favourite
Apartment in Wintergreen Resort
4.9 out of 5 average rating, 141 reviews

Panoramic Peak: Wintergreen Condo with Views

Top guest favourite
A cozy living room features comfortable seating on a sofa and armchair, complemented by a round coffee table. A smart TV is positioned above a fireplace with subtle artwork on the wall. Natural light filters through large windows, enhancing the inviting atmosphere.
Apartment in Wintergreen Resort
4.99 out of 5 average rating, 100 reviews

Stylish*Updated*Central*Walk to Slopes*Dogs OK!

Top guest favourite
A comfortable living area features a spacious gray sofa and a wooden coffee table, positioned on a patterned rug. Light from a nearby lamp and large sliding doors illuminates the space, which offers views of the outdoors. A cozy accent chair completes the inviting setup.
Apartment in Wintergreen Resort
4.95 out of 5 average rating, 217 reviews

New Construction! 1 Bed/2 Bath, pet friendly

Guest favourite
A cozy living area features natural stone accents around a wood-burning fireplace. A small dining table with two chairs is positioned near large windows, allowing ample natural light. Green accent walls enhance the inviting atmosphere, while a comfortable seating area is visible nearby.
Apartment in Wintergreen Resort
4.91 out of 5 average rating, 192 reviews

Tips Up: Cozy Slopeside Retreat w/ Fireplace

Guest favourite
Apartment in Wintergreen Resort
4.95 out of 5 average rating, 192 reviews

Ski-in/Ski-out Wintergreen Highlands Condo -Views!

Family-friendly house rentals

Top guest favourite
The exterior view showcases a modern blue house set against a backdrop of lush green hills. A wooden deck extends from the home, providing access to outdoor space. The gravel driveway is lined with a rustic split-rail fence, enhancing the natural feel of the surroundings.
Home in Nellysford
4.98 out of 5 average rating, 135 reviews

Llama Loft | Fire Pit | Fenced Yard | Nelson 151

Top guest favourite
A modern living area features a sleek leather sectional sofa adorned with patterned cushions, accompanied by a wooden coffee table. Large windows offer views of the surrounding trees, while natural light enhances the inviting space. A floor lamp adds illumination next to the sofa.
Home in Wintergreen Resort
4.96 out of 5 average rating, 112 reviews

Peaceful 3-BR Mountain home w/Fireplace + Hot tub

Guest favourite
A wooden walkway leads to the entrance of the house, framed by vibrant pink rhododendron flowers. Tall trees provide a natural backdrop, with dappled sunlight filtering through the leaves, creating a serene outdoor setting.
Home in Wintergreen Resort
4.95 out of 5 average rating, 130 reviews

Bear's Mountain Escape

Top guest favourite
A three-story wooden house is nestled among lush greenery in a forested setting. The deck and patio area are accessible, surrounded by trees and natural landscaping, creating a serene environment for relaxation.
Home in Nellysford
4.99 out of 5 average rating, 137 reviews

Cabin in Woods | Family & Dog Friendly | Fire Pit

Top guest favourite
The exterior of a cozy two-story mountain house is visible, featuring brown wooden siding and large windows. Leaves cover the ground, and a gravel driveway leads up to the home, surrounded by trees displaying autumn foliage.
Home in Wintergreen Resort
4.99 out of 5 average rating, 103 reviews

Cozy, relaxing mountain getaway on the golf course

Top guest favourite
A spacious bedroom features a high, wood-beamed ceiling and a large window providing natural light. The bed is dressed in navy bedding with a plaid blanket draped across it. A wooden dresser and lamp complement the rustic decor, and a mounted TV is positioned above.
Home in Wintergreen Resort
4.98 out of 5 average rating, 206 reviews

Hottub Ski In/Ski Out Renovated Chalet Lower Tyro

Guest favourite
An open living and dining area showcases warm wooden walls and a colorful area rug. A comfortable seating arrangement includes a sofa with pillows and a coffee table, while a dining table with white chairs is positioned nearby. Large windows allow natural light to fill the space.
Home in Wintergreen Resort
4.95 out of 5 average rating, 232 reviews

Saltbox at Wintergreen, a Modern Mountain Escape

Guest favourite
A cozy living space is highlighted by large windows that provide views of the surrounding trees. A comfortable sofa and armchair are arranged around a glass coffee table, complemented by a wooden dining set nearby. Warm wood accents are present in the ceiling beams and furnishings.
Home in Wintergreen Resort
4.81 out of 5 average rating, 127 reviews

Cozy Mountain Home Nestled in Nature!

Apartment rentals with air conditioning

Top guest favourite
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.
Flat in Staunton
5 out of 5 average rating, 176 reviews

Queen City Hideaway

Guest favourite
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.
Flat in Staunton
4.95 out of 5 average rating, 254 reviews

The Storefront: Downtown Staunton + Unique Stay

Top guest favourite
A two-story building is surrounded by lush greenery, with a spacious deck shaded by a red umbrella. Flowering plants and a bench are positioned in the front yard, inviting relaxation against the backdrop of the well-maintained exterior.
Flat in Staunton
4.99 out of 5 average rating, 441 reviews

Wildflowers Artist House

Top guest favourite
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.
Flat in Staunton
4.93 out of 5 average rating, 144 reviews

Walker's dream. Close to downtown.

Top guest favourite
A bright living room is furnished with a white leather sofa, accented by cushions and a red ottoman. A rocking chair sits next to a set of bookshelves. Natural light floods the space through large windows, with a colorful artwork visible on the wall in the background.
Flat in Staunton
4.93 out of 5 average rating, 605 reviews

Lewis Creek Loft

Guest favourite
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.
Flat in Afton
4.78 out of 5 average rating, 102 reviews

Earth Room Suite | Quiet Blue Ridge Retreat

Top guest favourite
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.
Flat in Staunton
4.97 out of 5 average rating, 456 reviews

The Bohemian Suite: Walk Downtown!

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.
Flat in Crozet
4.99 out of 5 average rating, 520 reviews

The Barn at Haden near Wineries and C'ville

Other great holiday rentals near Wintergreen Resort

Top guest favourite
The image showcases a cozy front porch featuring two rocking chairs, perfect for enjoying mountain views. The living area displays a comfortable couch and a stylish coffee table. A private hot tub is visible on the rear deck, complemented by scenic outdoor seating arrangements.
Cottage in Afton
4.97 out of 5 average rating, 148 reviews

Cottage on 151 w/ Hot Tub, Firepit, Mountain Views

Top guest favourite
The cottage is framed by lush greenery and trees, showcasing rustic wooden siding and a steeply pitched roof. Large windows allow natural light to fill the interior. A pair of rocking chairs is situated on the porch, inviting relaxation in a serene outdoor setting.
Cottage in Afton
4.99 out of 5 average rating, 267 reviews

Oasis in the Blue Ridge Rt. 151 Brew Ridge Trail

Guest favourite
The living area features a sectional couch, accented with striped throw pillows. Large windows provide ample natural light and scenic views of the outdoors. A small area rug adds warmth to the space, while a ceiling fan and built-in cabinetry contribute to the room's functionality.
Campervan/Motorhome in Afton
4.77 out of 5 average rating, 162 reviews

LaCasadeChiChi

Top guest favourite
A serene landscape showcases rolling hills adorned with autumn foliage. In the foreground, tall grass and scattered trees lead to a cozy house perched on a hillside, surrounded by vibrant fall colors. The distant mountains create a peaceful backdrop.
Yurt in Afton
5 out of 5 average rating, 948 reviews

Luxe Yurt w/Hot Tub in the Heart of the Blue Ridge

Guest favourite
The living area features a cozy red sofa and a wooden coffee table, complemented by a colorful area rug. A circular wooden dining table with four chairs sits nearby, illuminated by natural light from the large windows. A stone fireplace adds a rustic touch to the atmosphere.
Townhouse in Wintergreen Resort
4.94 out of 5 average rating, 198 reviews

Wintergreen home, ideal location, dogs welcome!

Top guest favourite
Four horses graze on a lush green lawn, with a charming two-story building in the background. The house features a balcony and is surrounded by blooming shrubs and trees, creating a serene atmosphere on the farm.
Farm stay in Afton
4.99 out of 5 average rating, 306 reviews

Afton, Mountain View Mini Farm

Top guest favourite
A contemporary home is showcased against a wooded backdrop, featuring large windows that enhance natural light. A spacious deck is fitted with seating and a dining table, inviting outdoor relaxation. Decorative string lights add a subtle charm, highlighting the entrance area.
Home in Nellysford
4.96 out of 5 average rating, 48 reviews

Glass & Pine, close to Bold Rock & Vineyards

Top guest favourite
A wooden sign painted in soft colors displays the name 'The Stable' in a flowing, artistic script. The background is a light gray with hints of gold, while the lettering features a warm rust tone, prominently positioned against a red door.
Guest house in Waynesboro
4.92 out of 5 average rating, 432 reviews

The Stable