
Vacation rentals in Wintergreen Resort
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Top-rated vacation rentals in 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.

Endless Mountain Top Views from All The Way Up!
Our warm and inviting condo combines amazing proximity to hiking with to-die-for views of the Blue Ridge Mountains and the horizon 75 MILES distant! Our condo sits a mere 400-yd walk from the closest hiking trail and also has direct access to the ridge line walking area - perfect place for a morning stroll! This updated and modern mountain themed space features: ✸ Newly renovated! ✸ Stocked modern kitchen! ✸ Two full bathrooms! ✸ Helix Hospitality Mattresses!! ✸ Cozy Fireplace w/ wood provided!

2 bdrm/2 full bath Best Views of Blue Ridge Mtns.
Best View of the Blue Ridge Mountains! Panoramic window views from the great room, dining area and kitchen. If you want to get a closer look step out on the observation deck to see the beautiful mountains and ski slopes (seasonal). Patio furniture is on the deck to enjoy morning sunrises and evening sunsets. All new stainless steel appliances in kitchen, Freshly painted throughout. 2 bedroom 2 bath Lots of activities to do at the Wintergreen Resort all year long. Year round resort activities.

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!

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

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- It's Pumpkin Spice Time!
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.

Sunset Vista Mountain Views “Skies for Miles”
Welcome to Sunset Vista Villa, where you enjoy, “Skies for Miles.” This beautiful, 2 bedroom, 2 bath, first-floor-unit with second story mountain views, is near all amenities the Wintergreen Resort has to offer. It comfortably sleeps five and with its western vistas, sunsets are a thing to behold! Whether you spend your days hiking, skiing or enjoying the wineries and breweries, SVV will enhance your stay. Book today & come enjoy the Wintergreen Resort and Blue Ridge Mountains!

2-min drive from 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 CLOSEDe

1 bedroom condo, hiking, breweries, wineries
Enjoy the mountains in the spring & summer enjoy hiking or a swim in the heapool! 1BR 1BA centrally located in Wintergreen 5 minute walk to Wintergreen resort Close to many hiking trails Enjoy the many breweries & wineries in the area Mountaintop Market is across the street 1 Bedroom 1 Bath & New queen sleeper sofa Stocked kitchen, cookware, spices & cooking oils Premium coffee & assorted tea Private furnished patio Wood burning fireplace, all you need for a quiet getaway

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 Wintergreen Resort vacation rentals
Other great vacation rentals in Wintergreen Resort

Premiere 2 BR Getaway Ski In/Out Wintergreen Condo

2 min to Slopes: Hot Tub, Gameroom, 3 King Beds

Perfect house

Beary Lazy - 4 beds and 2 sleeping sofas!

Buena Vista Panoramic Retreat: Million Dollar View

Luxe Modern Retreat: Steps to Ski & Hike! Views!

Mountain Views, Hiking, Ski-Out @ Tyro

Cozy 3BR/2BR+Fire table+Foosball
When is the best time to visit Wintergreen Resort?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $324 CAD | $322 CAD | $260 CAD | $251 CAD | $261 CAD | $247 CAD | $256 CAD | $249 CAD | $247 CAD | $263 CAD | $261 CAD | $294 CAD |
| Avg. temp | 2 °C | 4 °C | 8 °C | 14 °C | 18 °C | 22 °C | 24 °C | 23 °C | 20 °C | 14 °C | 9 °C | 4 °C |
Frequently Asked Questions
What types of vacation rentals are available in Wintergreen Resort?
Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Wintergreen Resort. From over 320 condo rentals to over 220 house rentals, we've got you covered.
Are there vacation rentals with a dedicated workspace in Wintergreen Resort?
Yes! Work meets play with ease at over 250 vacation rentals in Wintergreen Resort featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in house rentals in Wintergreen Resort?
Experience the best of Wintergreen Resort with our house rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there Wintergreen Resort house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 120 house rentals with pools in Wintergreen Resort, available on Airbnb. Make a splash and soak up the sun in style!
Are there pet-friendly vacation rentals in Wintergreen Resort?
Four-legged friends are welcome in Wintergreen Resort. Choose from more than 250 vacation rentals for guests traveling with pets.
Do house rentals in Wintergreen Resort have wifi?
Absolutely! We offer over 220 house rentals with wifi in Wintergreen Resort. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Wintergreen Resort have air conditioning?
Absolutely! We offer over 200 house rentals with air conditioning in Wintergreen Resort. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Wintergreen Resort have a gym?
Absolutely! We offer over 40 house rentals with a gym in Wintergreen Resort. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Wintergreen Resort have a bbq area?
Absolutely! We offer over 90 house rentals with a bbq area in Wintergreen Resort. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Wintergreen Resort?
Wintergreen Resort has more than 220 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Quick stats about vacation rentals in Wintergreen Resort

Total vacation rentals
Explore 700 vacation rentals in Wintergreen Resort

Nightly prices starting at
Wintergreen Resort vacation rentals start at $98 CAD per night before taxes and fees

Verified guest reviews
Over 25,830 verified reviews to help you choose

Family-friendly vacation rentals
550 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 250 rentals that welcome pets

Vacation rentals with a pool
450 properties feature pools

Rentals with dedicated workspaces
250 properties have a dedicated workspace

Wifi availability
690 of Wintergreen Resort vacation rentals include wifi access

Popular amenities for guests
Guests love Self check-in, Gym, and BBQ grill across Wintergreen Resort rentals

4.9 Average rating
Wintergreen Resort stays are highly rated by guests—averaging 4.9 out of 5!
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