
Holiday houses in Wintergreen Resort
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Top-rated holiday rentals in 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.

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!

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.

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!

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.

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.

BlueRidge Getaway- Dog Friendly
Relax and enjoy spectacular top-floor mountain views from the deck. This recently renovated unit is at the top of the mountain close to many hiking trails. Visit the Wintergreen village, with its restaurants and shops, with a 5 minute drive or an easy hike through the woods. You also have access to Rhodes Farm and Chestnut Hills pool. This condo is convenient to Devils Backbone, Bold Rock, and the litany of other breweries, cideries, distilleries, and restaurants. Dogs welcome!

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 holiday rentals
Other great holiday rentals in Wintergreen Resort

Premiere 2 BR Getaway Ski In/Out Wintergreen Condo

Weller’s Retreat at Stone Ridge

Blue Ridge Treehouse

Beary Lazy - 4 beds and 2 sleeping sofas!

Wintergreen Mountain Views - Diamond in the Slopes

4 min to Ski: Whispering Creek Hot Tub King Beds

Wintergreen Best location,Arcades,king bed,2 room

Mountain Views, Hiking, Ski-Out @ Tyro
When is the best time to visit Wintergreen Resort?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $382 NZD | $379 NZD | $306 NZD | $296 NZD | $308 NZD | $291 NZD | $301 NZD | $293 NZD | $291 NZD | $349 NZD | $353 NZD | $437 NZD |
| 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 holiday rentals in Wintergreen Resort

Total holiday rentals
Explore 710 holiday rentals in Wintergreen Resort

Nightly prices starting at
Wintergreen Resort holiday rentals start at $132 NZD per night before taxes and fees

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

Family-friendly holiday rentals
560 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 270 rentals that welcome pets

Holiday 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 holiday 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
- Wintergreen Resort
- Frontier Culture Museum
- Blenheim Vineyards
- Amazement Square
- Homestead Ski Slopes
- Liberty Mountain Snowflex Centre
- Glass House Winery
- Cardinal Point Winery
- University of Virginia
- John Paul Jones Arena
- Devils Backbone Brewing Co Basecamp
- James Madison University
- White Lotus Eco Spa Retreat
- Monticello
- Virginia Horse Center
- The Rotunda
- Grand Caverns
- White Oak Lavender Farm & The Purple WOLF Vineyard
- IX Art Park
- James River State Park




