
Places to stay near Wintergreen Resort
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Top-rated vacation rentals near Wintergreen Resort
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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.

Bear's Mountain Escape
Dog friendly, 3 BR, 2 BA, loft style condo located in the heart of the Wintergreen Resort. Ski check-in, restaurants, the mountaintop market, & The Mountain Inn are all right across the street! 2-story unit with a main floor primary BR & hall bath. Main floor bonus room with single & trundle. The loft contains 2 twin beds and the 2nd full bath. Parking, pool, washer/dryer, and Wi-Fi included. Fully stocked kitchen, wood burning fireplace, balcony, all towels/linens provided. Sleeps up to six.

Five Minute Walk to Everything!
**Pet friendly** two bedroom, two bath, loft style condo centrally located at Wintergreen Resort. Ski check-in/lifts, 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 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.

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!

Stylish*Updated*Central*Walk to Slopes*Dogs OK!
Step into the allure of our fantastic Wintergreen, just a leisurely 4min stroll away from the heart of Wintergreen's mtn action! Tucked away in a serene and tranquil nook of the mountain, our meticulously curated property combines serene relaxation with unfettered access to the thrilling outdoor adventures that await nearby. The closest hiking trail is within 200 yds! Whether you're a couple seeking a romantic retreat or a small, fun family, our home is eager to embrace your mountain dreams!

2-min drive to 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 CLOSED for season

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.

3 BR 3 BA, 2 story condo in Highlands
Newly renovated condo! You can't beat the view from up here. Top floor/vaulted ceilings, next to the Highlands Lift. Just steps from the expert slopes and on the Wintergreen shuttle route. Enjoy hiking, skiing, snowboarding, tubing, outdoor pool time or a local brewery. This condo has 2 master's with king beds, 1 bunk bed (twin over full), a single twin bed and a pull out twin sleeper sofa. The king beds have new high quality mattresses and luxury bedding and a 60" HDTV in living room

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.

Mountain View Nest
From the moment you walk in, this condo offers endless opportunities to relax and retreat. The sweeping mountain views over the back deck provide the ideal setting for a romantic getaway, a girls weekend, or much needed time to recharge. This one bedroom/bathroom unit with a king sized bed, fully stocked kitchen, and artistic decor is located on the third floor of the Ledges. It is the perfect location for those who ski, hike, golf, or taste the flavors from local wineries.

Ski-In Ski-Out ~ Mtn Views ~ King Suite
Just steps from Wintergreen Resort’s slopes, Slope Side Gem offers the perfect mountain escape! Located in the heart of Mountain Village next to the Mountain Inn, you’re just a short walk to Starbucks, The Market, shops, and three restaurants and bars. Whether you’re skiing, hiking, golfing, or enjoying a local brewery or winery, adventure is at your doorstep. After an exciting day, unwind on the private balcony and take in the breathtaking mountain views!
Popular amenities for vacation rentals near Wintergreen Resort
Condo rentals with wifi

The Modern Mountain Condo

Cozy getaway with heated floors

Mountain Views

New Construction! 1 Bed/2 Bath, pet friendly

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

Cozy, clean, quiet mountain condo- King bed

Cozy Comfort with a View - Wintergreen Resort

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

Stargazing on 12 Acres: Hot Tub 55"TV Fire Pit

Cliffs Edge -A Contemporary Mountain Home

Hilltop at Mountain View Meadow

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

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

The Cozy Cottage | Mountain views at Wintergreen

Cabin Getaway | Family & Dog Friendly | Fire Pit

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

The Hideaway Suite: Sauna & Lux Amenities

The Storefront: Downtown Staunton + Unique Stay

Spacious 2 bedroom, 2 bath condo w/ full kitchen

Walker's dream. Close to downtown.

Lewis Creek Loft

The Shenandoah Suite: Private Balcony, Walkable

Endless Mountain Top Views from All The Way Up!

The Barn at Haden near Wineries and C'ville
Other great vacation rentals near Wintergreen Resort

Best Blue Ridge Views at Sunrise over Wintergreen

Cozy 1-bedroom Condo with Fireplace Near Ski Slope

Premiere 2 BR Getaway Ski In/Out Wintergreen Condo

Wintergreen Mountain Views - Diamond in the Slopes

Timbers Lodge 39 with Wintergreen Advantage

Spacious Ski In Ski Out Condo with Mountain View

Cozy Wintergreen Condo 5 minute walk to slopes

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




