
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!

Romantic Yurt~On 151 Brew Trl~Nat. Park & DB 5 min
Come for a memorable stay at the Rockfish Valley Yurt and enjoy "glamping" at its finest! Picturesque mountain views await at this magical yurt conveniently located ON the “151 Brew Ridge Trail", on 3 acres close to popular attractions- Nat. Park & hiking 2 mi, Lake 10 mi, Devils Backbone Brewery 1 mi, Bold Rock 2 mi & Wintergreen Spa/Ski/Tube 10 mi. You’ll have 15+ wineries & breweries within a 20 min radius. It’s a one of a kind experience here! Create memories that will last a lifetime!

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.

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 Log Cabin
Relax and unwind in this secluded, hand-hewn log cabin with all the modern conveniences. 10 minutes off the Blue Ridge Parkway from mile marker 16, minutes from Shenandoah National Park and the Appalachian Trail, close to 4 breweries, 6 wineries, 3 cideries, and Wintergreen Four-Season Resort. Located on over 300 acres of private land with plenty of room to explore and enjoy the wildlife. Come witness the brilliant night sky lying in an open field with no city lights to diminish the experience.

Gorgeous Modern Mountain Home + Blue Ridge Views
GREENWOOD VISTA - Escape to our modern mountain retreat nestled along the Blue Ridge mountains. Whether you want to explore Shenandoah National Park, visit wineries, or relax in our hot tub with stunning mountain views, this gorgeous A-Frame home is the perfect place for you. We have thoughtfully appointed our home with everything you need to be comfortable. From a luxurious bedroom suite, fully equipped kitchen, to coffee and wet bar, sauna, outdoor grill, billiard table, and a cozy fire pit.

Mountain Hideaway Cottage
Perfect for couples or families. Tucked away on its own private mountain acreage with stream access. Large screened porch for talking into the night or enjoying your morning coffee. Ask about same day after 5pm discount! Less than 2 miles to Devil's Backbone and Bold Rock. Minutes to Blue Ridge Parkway,Appalachian Trail, Wintergreen, breweries, wineries, cideries, restaurants, horseback riding, hiking, mountain lakes, & antique shopping. Gas fireplace. 1G WiFi & SMART TV. Fire pit and wood.

The Modern Mountain Condo
Conveniently located within the 4-season Wintergreen Resort, this recently renovated condo offers a quiet and cozy stay while you take in the mountain views and enjoy endless outdoor activities, wineries, breweries, restaurants, and antique shops. Rest and recharge while you enjoy the light-filled, open floor plan with a wood-burning fireplace, a kitchen with plenty of cabinet space, and full-sized appliances for cooking. Private patio and community pool access are located outside the unit.

Luxe Yurt w/Hot Tub in the Heart of the Blue Ridge
Experience glamping, Blue Ridge style. Our luxury yurt is located at the top of a small hill, in the center of a 70 acre farmstead surrounded by natural beauty. Night Archer Farm is located off a quiet country road in Afton, Nelson County. It is private, but not remote. You are close to the Brew Ridge trail, wineries, breweries, skiing at Wintergreen, Blue Mountain Brewery, Devil's Backbone, golf, hiking, or driving the Blue Ridge Parkway. Hike directly from the Yurt up into the mountains!

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.
Popular amenities for holiday rentals near Wintergreen Resort
Condo rentals with Wi-Fi

Five Minute Walk to Everything!

Eight Minute Walk to Everything

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

Third & Thornrose, Staunton Condominium

Panoramic Peak: Wintergreen Condo with Views

Panoramic Views | Sunrise on the Deck | Nelson 151

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

Sunset Vista Villa, Mountain Views-Close to Slopes
Family-friendly house rentals

Cliffs Edge -A Contemporary Mountain Home

Pine Lake Lodge

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

The Cozy Cottage | Mountain views at Wintergreen

Bear's Mountain Escape

Perfect getaway among the orchards of Batesville

Little Yellow House: Walk to Downtown Staunton

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

The Storefront: Downtown Staunton + Unique Stay

Walker's dream. Close to downtown.

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

Willow Ridge

⭐Private Apartment Footsteps From Downtown
Other great holiday rentals near Wintergreen Resort

Tiny Luxury Retreat: Lake, Hikes, Brews & Vines

Guesthouse at Hamilton Oaks

Cozy Mountain Cottage on Brew/Wine Trail-King Bed

The Nest...lovely 2 bedroom apartment in the woods

140 Acres River trails, Private! Ski Wintergreen!

Buena Vista Panoramic Retreat: Million Dollar View

Spacious Ski In Ski Out Condo with Mountain View

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
- Liberty Mountain Snowflex Centre
- Cardinal Point Winery
- Glass House Winery
- John Paul Jones Arena
- University of Virginia
- Monticello
- Virginia Horse Center
- The Rotunda
- James Madison University
- White Lotus Eco Spa Retreat
- Grand Caverns
- IX Art Park
- James Madison's Montpelier
- James River State Park
- Natural Bridge State Park




