
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.

NO STEP ENTRY Wintergreen Mtn Home,HotTub,Sleeps10
We had to create a new listing for this property. Previous listing had 70+ reviews with a 4.8 Star rating. Same great host and same great house, just a new listing. Screenshots of old listing in additional photos. Stay at this luxurious 4-bedroom, 3-full bath vacation rental home for 10 in Wintergreen, within minutes of top-notch golf courses, skiing / snow boarding at the Mountain Inn, and dozens of hiking trails . In addition to the unbeatable location, the property offers a private hot tub!

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!

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.

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.

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
Wintergreen Resort house rentals

Cozy 5-bedroom home for large gatherings.

Mountain Retreat: Year-Round Getaway, Pup Friendly

Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat

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

Glass House | Mountain & Water Views @ Wintergreen

Saltbox at Wintergreen, a Modern Mountain Escape

Ridge Retreat @ Wintergreen!

Cozy Wintergreen Townhome
Ski-in/ski-out vacation rentals in Wintergreen Resort

Spacious 2 bedroom, 2 bath condo w/ full kitchen

Cozy Cabin+Walk to Ski *Hot Tub* Mtn Vibe

Mountain 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!

Ski- In/Ski-Out Comfy Condo

Ski-in/Ski-out Wintergreen Highlands Condo -Views!
Ski-in/ski-out houses in Wintergreen Resort

Premiere 2 BR Getaway Ski In/Out Wintergreen Condo

Wintergreen Condo~ 1 Minute To Four Seasons Resort

Perfect House

Walk to Ski! Cliff Hanger Hot Tub Fireplace DogsOK

WalktoSki! Just steps from Eagles Swoop! Views!

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

Hottub Ski InOut Renovated Chalet Lower Tyro Slope

Find YOUR Magic
When is the best time to visit Wintergreen Resort?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ848 | ﺩ.ﺇ841 | ﺩ.ﺇ679 | ﺩ.ﺇ657 | ﺩ.ﺇ683 | ﺩ.ﺇ646 | ﺩ.ﺇ668 | ﺩ.ﺇ650 | ﺩ.ﺇ646 | ﺩ.ﺇ687 | ﺩ.ﺇ683 | ﺩ.ﺇ768 |
| 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
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 self check-in?
Absolutely! We offer over 90 house rentals with self check-in 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.
What are the most popular amenities for House Rentals in Wintergreen Resort?
Enhance your stay in our House Rentals with the most popular amenities: over 90 homes with self check-in, over 40 homes with a gym, over 220 homes with wifi, over 90 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about vacation rentals in Wintergreen Resort

Total vacation rentals
Explore 710 vacation rentals in Wintergreen Resort

Nightly prices starting at
Wintergreen Resort vacation rentals start at ﺩ.ﺇ294 per night before taxes and fees

Verified guest reviews
Over 26,760 verified reviews to help you choose

Family-friendly vacation rentals
560 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 270 rentals that welcome pets

Vacation rentals with a pool
460 properties feature pools

Rentals with dedicated workspaces
260 properties have a dedicated workspace

Wi-Fi availability
710 of Wintergreen Resort vacation rentals include wi-fi 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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- Shenandoah National Park
- Early Mountain Winery
- Downtown Mall
- James Monroe's Highland
- Amazement Square
- Frontier Culture Museum
- Blenheim Vineyards
- Wintergreen Resort
- Homestead Ski Slopes
- Liberty Mountain Snowflex Centre
- Cardinal Point Winery
- Glass House Winery
- James Madison University
- Devils Backbone Brewing Co Basecamp
- University of Virginia
- Monticello
- John Paul Jones Arena
- White Lotus Eco Spa Retreat
- Natural Bridge State Park
- The Rotunda
- Grand Caverns
- Virginia Horse Center
- Percival's Island Natural Area
- IX Art Park




