
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.

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.

Ultimate cabin in the mountains
This unique and secluded cabin sits on 75 acres in the Blue Ridge mountains. Enjoy the cozy wood fireplace, hot tub, charcoal grill, and fast, reliable fiberoptic internet if you need to get some work done while you're away. It has a washer and dryer, a full kitchen, and is pet-friendly (no pet fee!), so you can enjoy it with the whole family. There is a 4K 55” smart TV with apps, a Tesla LVL 2 charger, a cabinet full of board games, books, and plenty of items to entertain both kids and adults!

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

Hottub Ski InOut Renovated Chalet Lower Tyro Slope
Completely renovated, 3 BR/2BA chalet, located on Lower Tyro slope, just below Tequila. Rustic decor, fully stocked kitchen, high end appliances, granite counters. Open floor plan, walls of windows, mtn views. Beautiful stone fireplace, ample comfortable seating. 2 main floor Masters, each w/King bed, TV, luxurious bedding. Loft is a dedicated kids space: 2 sets of bunks, daybed w/trundle, TV & PS4. Gas grill, 6 person hot tub. Perfect ski home to host 2 Families, or a romantic couple's getaway.

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.

Elk Mountain Overlook: Breathtaking Views
Mountaintop overlook with jaw dropping views and camp themed interior design. Perched upon Elk Mountain just off the Blue Ridge Parkway this petite chalet is under 30 min from Charlottesville, 10 min to 151 vineyards/breweries/cideries, and 10 min to Waynesboro. Relax in this natural retreat featuring 2 king bedrooms, 2 person soaker tub, double headed shower, and ample kitchen w/many extras. Take in the views from the large deck, firepit, under porch swing, or mountainside adirondack chairs.

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!

Eight Minute Walk to Everything
This one-bedroom, one-bath condo is centrally located. Ski check-in, restaurants, the mountaintop provisions market, and the Mountain Inn and conference center are all within an 8 minute walk. It's a one-story, downstairs unit that includes a back porch with just a few steps down to the ground. Perfect for taking the dog outside in the pet-friendly space. Full kitchen and dishes, wood-burning fireplace, balcony, and all towels and linens are provided for your convenience. Sleeps 3.

1 bedroom condo, walk to the slopes !
Cozy 1BR Wintergreen condo ⛷️❄️ 5-minute walk to the ski slopes, resort village, and mountain-too market, with snow tubing only minutes away. Enjoy a fully stocked kitchen, premium coffee and teas, cooking oils and spices. Relax by the wood burning fire and enjoy a smart TV, fast WiFi and games. Comfortable queen bed in the bedroom plus new queen sleeper sofa in the living room. Private furnished patio with peaceful wooded views and close access to the village for après-ski.

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.

Cliffs Edge -A Contemporary Mountain Home
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.

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
Condo rentals with Wi-Fi

The Modern Mountain Condo

Blue Ridge Retreat: Your Cozy Mountain Getaway

Cozy Condo - Sleeps 4

Five Minute Walk to Everything!

Wintergreen Resort King bed, Fire place, 2 Bd/2 Br

Tips Up: Cozy Slopeside Retreat w/ Fireplace

Cozy Comfort with a View - Wintergreen Resort

Cozy Laurelwood condo - 10 min walk to slopes
Family-friendly house rentals

Pine Lake Lodge

Hot Tub, Firepit, Mtn Views, Walk to Coffee & Park

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

The Cozy Cottage | Mountain views at Wintergreen

Bear's Mountain Escape

Cabin Escape | Family & Dog Friendly | Fire Pit

Beauty in the Shenandoah Valley

Saltbox at Wintergreen, a Modern Mountain Escape
Apartment rentals with air conditioning

Queen City Hideaway

The Storefront: Downtown Staunton + Unique Stay

Wildflowers Artist House

Spacious 2 bedroom, 2 bath condo w/ full kitchen

Lewis Creek Loft

The Barn at Haden near Wineries and C'ville

Endless Mountain Top Views from All The Way Up!

Studio Apt. in Wine/Brewery Country/on 151
Other great holiday rentals near Wintergreen Resort

Best Blue Ridge Views at Sunrise over Wintergreen

Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat

Unique Stay on 151 Brew Trail~Nat. Park & DB 5 min

Cozy Cabin+Walk to Ski *Hot Tub* Mtn Vibe

Condo with Valley Views!

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

The Cottage at Spindle Hill: an Artist’s Farm

Glass & Pine, close to Bold Rock & Vineyards
Destinations to explore
- Shenandoah National Park
- Early Mountain Winery
- Downtown Mall
- James Monroe's Highland
- Frontier Culture Museum
- Homestead Ski Slopes
- Blenheim Vineyards
- Amazement Square
- Devils Backbone Brewing Co Basecamp
- Cardinal Point Winery
- Liberty Mountain Snowflex Centre
- John Paul Jones Arena
- Glass House Winery
- Monticello
- University of Virginia
- Virginia Horse Center
- James Madison University
- The Rotunda
- Grand Caverns
- White Lotus Eco Spa Retreat
- IX Art Park
- James Madison's Montpelier
- James River State Park
- White Oak Lavender Farm & The Purple WOLF Vineyard




