
Places to stay near Wintergreen Resort
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Top-rated vacation rentals near Wintergreen Resort
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Close to hiking! | 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

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.

Panoramic Sunsets, Mountain Views, Private Deck.
Wake up above the mountains and end your day with unforgettable sunset views some of the best on the mountain. Sunset Vista Villa is a cozy retreat designed for slowing down, morning coffee on the deck, evenings by the fire. With two private bedrooms, each with its own en-suite bathroom, its perfect for couples or friends. Easy entry with just a few steps, yet elevated views make this stay both convenient and special. Ask us about early check-in or late check-out to enjoy even more of the view

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!

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.

1 bedroom condo, close to hikes & breweries & pool
Cozy 1BR Wintergreen condo 🌳 🌄 Close to scenic hikes, local breweries and wineries. The resort village, and mountain-top market, just minutes away. Enjoy a fully stocked kitchen, premium coffee and teas, cooking oils and spices. Relax after a day outdoors 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 or cool off in the heated community pool.

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!

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!

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!
Popular amenities for vacation rentals near Wintergreen Resort
Condo rentals with wifi

Where the Trail Ends

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

Five Minute Walk to Everything!

Eight Minute Walk to Everything

Mountain Views

Panoramic Peak: Wintergreen Condo with Views

2-min drive to resort, Outdoor HOA pool opens 5/25

Cozy Comfort with a View - Wintergreen Resort
Family-friendly house rentals

Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat

Private Pool Opens April 1 - All Year Hot Tub

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

Llama Loft | Fire Pit | Fenced Yard | Brew Trail

The Cozy Cottage | Mountain views at Wintergreen

Bear's Mountain Escape

Saltbox at Wintergreen, a Modern Mountain Escape

Mountain Bauhaus | Sleeps 8 | Amenities | Grill
Apartment rentals with air conditioning

Queen City Hideaway

Walk to Market/Slopes!

The Storefront: Downtown Staunton + Unique Stay

Wildflowers Artist House

The Barn at Haden near Wineries and C'ville

Endless Mountain Top Views from All The Way Up!

Blue Ridge Bliss - For family & friends to enjoy!

Willow Ridge
Other great vacation rentals near Wintergreen Resort

Best Blue Ridge Views at Sunrise over Wintergreen

Elk Mountain Overlook: Breathtaking Views

Wintergreen Mountain Views - Diamond in the Slopes

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

Wintergreen home, ideal location, dogs welcome!

The Cottage at Spindle Hill: an Artist’s Farm

Beautiful Mountain Getaway - Walk to Everything!

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





