
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!

Tips Up: Cozy Slopeside Retreat w/ Fireplace
The mountains are calling and you must go. Well, you don't have to, but we think it's a good idea. Make Tips Up your home while you're away. With slopeside views, a cozy and comfortable ambiance, and close proximity to skiing (only 100 yards from the slopes!) and hiking, this 1B/1BA condo is the perfect getaway for outdoor enthusiasts seeking a mountain escape. Relax at nearby breweries and wineries with unbeatable views, and return to your condo to enjoy the amenities of Wintergreen Resort.

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, close to hikes & breweries
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.

Cozy Laurelwood condo - 10 min walk to slopes
This beautiful 1-bedroom, 1-bath Laurelwood condo is perfectly located just a short walk from the pool, market, coffee shop, restaurants, and the Wintergreen Conference Center. Inside, you’ll find a fully equipped kitchen, a cozy wood-burning fireplace (with complimentary firewood), and a spacious king-size bed. Step outside to your private deck and enjoy the peace of the surrounding forest—an ideal retreat for relaxation and comfort.

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!

Panoramic Peak: Wintergreen Condo with Views
Panoramic Peak is situated in the heart of Wintergreen Resort and boasts stunning mountain views from every window. The condo is one bedroom with 2 full bathrooms, but the unit comfortably sleeps four with a well-appointed sleeper sofa in the living area. During summer months, guests have access to the Chestnut Springs and Rodes Valley Pools.

Ski-in/Ski-out Wintergreen Highlands Condo -Views!
Come escape! Newly updated with fresh paint, floors, furniture, and finishes! Sleeps 7. Our condo sits in the heart of Devils Knob and at the top of the Highlands Express Ski Lift. Steps away from Upper Cliffhanger, Upper Wild Turkey and Outer Limits ski runs.
Popular amenities for holiday rentals near Wintergreen Resort
Condo rentals with Wi-Fi

The Modern Mountain Condo

Cozy Condo - Sleeps 4

Five Minute Walk to Everything!

Ski-In Ski-Out ~ Mtn Views ~ King Suite

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

1720 High Ridge at Wintergreen Resort

Panoramic Views | Sunrise on the Deck | Nelson 151

Panoramic Sunsets, Mountain Views, Private Deck.
Family-friendly house rentals

The Be Kind House

“Small" House/Peaceful/Brewery/Hike/Winery/River

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

The Cozy Cottage | Mountain views at Wintergreen

Bear's Mountain Escape

Cabin Retreat | Family & Dog Friendly | Fire Pit

Beauty in the Shenandoah Valley

Hottub Ski InOut Renovated Chalet Lower Tyro Slope
Apartment rentals with air conditioning

The Storefront: Downtown Staunton + Unique Stay

Wildflowers Artist House

Spacious 2 bedroom, 2 bath condo w/ full kitchen

Earth Room Suite | Quiet Blue Ridge Retreat

Traveler’s Escape-1 bedroom. Walk to downtown!

The Barn at Haden near Wineries and C'ville

Endless Mountain Top Views from All The Way Up!

The Bons Amis Suite: Chic Decor, Walk Downtown
Other great holiday rentals near Wintergreen Resort

Elk Mountain Overlook: Breathtaking Views

Cozy Mountain Cottage on Brew/Wine Trail-King Bed

The Laurel Hill Treehouse

The Distinguished Squirrel Chalet walking distance

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

The Cottage at Spindle Hill: an Artist’s Farm

Historic cottage with stunning mountain views

Gorgeous Modern Mountain Home + Blue Ridge Views
Destinations to explore
- Shenandoah National Park
- Early Mountain Winery
- University of Virginia
- Downtown Mall
- James Monroe's Highland
- Blenheim Vineyards
- Frontier Culture Museum
- Cardinal Point Winery
- Homestead Ski Slopes
- Devils Backbone Brewing Co Basecamp
- Amazement Square
- John Paul Jones Arena
- Liberty Mountain Snowflex Centre
- Monticello
- Glass House Winery
- James Madison University
- Virginia Horse Center
- The Rotunda
- Grand Caverns
- White Lotus Eco Spa Retreat
- James Madison's Montpelier
- Natural Bridge State Park
- IX Art Park
- James River State Park




