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

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

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.

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.

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 master suite, fully equipped kitchen, to coffee and wet bar, sauna, outdoor grill, billiard table, and a cozy fire pit.

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!

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!

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

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.

Cozy Comfort with a View - Wintergreen Resort
Our private, spacious, dog friendly condo is just a 5 minute walk to the main lodge with shops, restaurants, and of course the slopes! Shuttles run during ski season as well. Beautiful hiking trails are just outside the door, and a short drive will get you to the Blue Ridge Parkway, Crabtree Falls, Stoney Creek Golf Course, and the famous Route 151 with Virginia's finest breweries and wineries. There is a community pool available in Wintergreen Resort during the summer months.
Popular amenities for holiday rentals near Wintergreen Resort
Condo rentals with Wi-Fi

The Modern Mountain Condo

All-Season 2bd/2ba next to Spa view of Golf Course

Five Minute Walk to Everything!

Eight Minute Walk to Everything

Mountain Views

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

New Construction! 1 Bed/2 Bath, pet friendly

Ski-in/Ski-out Wintergreen Highlands Condo -Views!
Family-friendly house rentals

Cliffs Edge- “Available Again This Weekend !’

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

Centrally located home on the brew trail

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

Bear's Mountain Escape

Cabin in Woods | Family & Dog Friendly | Fire Pit

Saltbox at Wintergreen, a Modern Mountain Escape

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

Queen City Hideaway

Best Spot on the Wine/Brew Trail!

Mountain View Nest

Walker's dream. Close to downtown.

Lewis Creek Loft

Endless Mountain Top Views from All The Way Up!

The Barn at Haden near Wineries and C'ville

The Urban Cowboy Suite: Walk Downtown!
Other great holiday rentals near Wintergreen Resort

Tiny Luxury Retreat: Lake, Hikes, Brews & Vines

Ultimate cabin in the mountains

Afton, Mountain View Mini Farm

Lakefront Cabin w Stunning Curated Decor & Hot Tub

Mountain View Vista: Resort Condo w/ Views

Glass & Pine, close to Bold Rock & Vineyards

Owl Bnb | Walkable to Slopes | Speakeasy Room

On the Slopes- Swoopside Hideaway- Prime Location
Destinations to explore
- Early Mountain Winery
- Boonsboro Country Club
- The Plunge Snow Tubing Park
- Amazement Square
- Massanutten Ski Resort
- James Monroe's Highland
- Homestead Ski Slopes
- Chisholm Vineyards at Adventure Farm
- Liberty Mountain Snowflex Centre
- Frontier Culture Museum
- Spring Creek Golf Club
- Blenheim Vineyards
- Farmington Country Club
- Birdwood Golf Course
- Cardinal Point Winery
- Glass House Winery
- Meriwether Springs Vineyard and Brewery
- Monticello
- Burnley Vineyards




