
Condo vacation rentals in Wintergreen Resort
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Top-rated condo rentals in 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.

Sunset Vista Villa, Mountain Views-Close to Slopes
Welcome to Sunset Vista Villa, Mountain Views & Close to Slopes (on the shuttle route) This beautiful, 2 bedroom, 2 bath, first-floor-unit with top 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!

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.

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!

Mountain View Condo at Wintergreen, Fireplace
Breathe in the crisp mountain air, cozy up by the fireplace, and soak in sweeping views of the Blue Ridge Mountains. This clean, comfortable 2-bedroom condo at Wintergreen Resort features two king beds, two full bathrooms, and a sleeper sofa—perfect for up to 6 guests. Enjoy panoramic windows overlooking the mountains,, a fully stocked kitchen, in-unit washer/dryer, central heat/AC, and free parking. The shuttle to the ski lodge is just steps away!

Wintergreen Resort King bed, Fire place, 2 Bd/2 Br
Forget your worries in this spacious and serene space. Condo has been completely renovated and can be enjoyed all year round! Located between the Wintergarden Spa, the Nature Foundation and the Devils Knob Sports Center (golf, tennis and fine dining restaurant) Stone Ridge neighborhood is centrally positioned to most of the Resort amenities. 5 min drive to slopes 5 mins to Market 15 to Devils Backbone 3 mins to Devils Knob golf course
Popular amenities for Wintergreen Resort condo rentals
Weekly condo rentals

Fireworks & Mountain Views Ski In/Out Studio in WG

Wintergreen Resort Condo- 440 Three Ridges

Retreat @ 3 Ridges | 3 min walk to Slopes/Dining

Wintergreen Ski Retreat, Cozy Condo Near Slopes

Wintergreen! Dog friendly, cozy and comfortable

Lovely Ski Front Private 3-bed/3-bath condo

Wintergreen Condo -Steps to Ski

Slope Views, Aspen Suite — 2 Fireplaces
Pet-friendly condo rentals

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

Condo with Valley Views!

Timbers Lodge 39 with Wintergreen Advantage

1720 High Ridge at Wintergreen Resort

Recently updated - views of the Blue Ridge Mtns

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

Cozy, clean, quiet mountain condo- King bed

Mountain top 3-bedroom condo with spectacular view
Condo rentals with a pool

Steps to the Slopes-Relax in comfort

Cozy condo! Short walk to the slopes and trails.

On the mountain, pet and child friendly

Nature’s Haven 1 Bedroom Condo Wintergreen Resort

A Mountain Escape-Cozy Condo for 2 to 4

3 Ridges 3 min walk to slopes,besides inn,King bed

Overlook 180 degree views w/Peloton!

Wintergreen Retreat- 3 min walk to slopes.
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.ﺇ580 | ﺩ.ﺇ580 | ﺩ.ﺇ507 | ﺩ.ﺇ474 | ﺩ.ﺇ459 | ﺩ.ﺇ459 | ﺩ.ﺇ503 | ﺩ.ﺇ477 | ﺩ.ﺇ474 | ﺩ.ﺇ499 | ﺩ.ﺇ499 | ﺩ.ﺇ529 |
| 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 |
Quick stats about condo rentals in Wintergreen Resort

Total vacation rentals
Explore 320 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 9,750 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 80 rentals that welcome pets

Vacation rentals with a pool
250 properties feature pools

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
320 of Wintergreen Resort vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool 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
- Frontier Culture Museum
- Blenheim Vineyards
- Amazement Square
- Wintergreen Resort
- 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




