Holiday houses in Wintergreen Resort
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Quick stats about holiday rentals in Wintergreen Resort
Total holiday rentals
Explore 770 holiday rentals in Wintergreen Resort
Nightly prices starting at
Wintergreen Resort holiday rentals start at $121 NZD per night before taxes and fees
Verified guest reviews
Over 28,350 verified reviews to help you choose
Family-friendly holiday rentals
580 properties offer extra space and kid-friendly amenities
Pet-friendly accommodation
Find 260 rentals that welcome pets
Holiday rentals with a pool
500 properties feature pools
Rentals with dedicated workspaces
240 properties have a dedicated workspace
Wi-Fi availability
770 of Wintergreen Resort holiday rentals include Wi-Fi access
Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Wintergreen Resort rentals
4.9 Average rating
Wintergreen Resort stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated holiday rentals in Wintergreen Resort
Guests agree: these stays are highly rated for location, cleanliness and more.
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!
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!
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.
Wintergreen Getaway
Relax with the whole family at this peaceful place to stay. Enjoy morning coffee and evening cocktails on the deck fronting the golf course. You will love the location and features! Walking distance to spa, The Wintergreen Nature Foundation, and Fire & Frost. Convenient to slopes, Chestnut Springs pool and Upper Shamokin Falls. A great place to relax after a full day of hitting nearby slopes or hiking trails, and exploring Nelson 151's winery and brewery attractions. Stairs to access. WiFi!
2-min drive to resort, Outdoor HOA pool now open!
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
Saltbox at Wintergreen, a Modern Mountain Escape
Your mountain adventure awaits at Saltbox, an inviting, eclectic home at Wintergreen Resort in the Blue Ridge Mountains. Combining modern and vintage decor, plus original art, Saltbox was designed to provide escape, inspiration and fun. Nestled at the end of a quiet cul-de-sac drive, with beautiful woods to explore, it's just seconds from the Resort (skiing, tubing, hiking, dining, spa, outdoor movies and more)! Saltbox is the perfect home base for your next getaway, any time of year!
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 -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.
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!
Cozy Cabin+Walk to Ski *Hot Tub* Mtn Vibe
Renovated 3BR/2.5BA mountain home is just a short walk to ski slopes, hiking trails, and resort amenities. Enjoy a private hot tub, stone fireplace, deck with views, gas fire pit, and grill. Kids will love the bunk room and loft with Buck Hunter arcade & games. Smart TVs with streaming in main living and bunk room. Fully stocked kitchen + washer/dryer. Perfect for ski trips, hiking getaways, winery weekends, or a relaxing mountain escape
Popular amenities for Wintergreen Resort holiday rentals
Other great holiday rentals in Wintergreen Resort
Best Blue Ridge Views at Sunrise over Wintergreen
Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat
Ski-In Ski-Out ~ Mtn Views ~ King Suite
Blue Ridge Treehouse
Condo with Valley Views!
Mountain View Vista: Resort Condo w/ Views
NO STEP ENTRY Wintergreen Mtn Home,HotTub,Sleeps10
The Perch in Wintergreen Laurelwood
When is the best time to visit Wintergreen Resort?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $493 NZD | $477 NZD | $359 NZD | $311 NZD | $323 NZD | $305 NZD | $316 NZD | $307 NZD | $305 NZD | $366 NZD | $370 NZD | $458 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
What are the best places to stay in Wintergreen Resort?
Stay in mountain-side homes, condos, or woodland cottages around Wintergreen Resort. These options have easy access to amenities, scenic views, and outdoor activities, making them frequently suggested for visitors.
What are the best things to do in Wintergreen Resort with kids?
Families can explore nature trails, visit the adventure park for ziplining or mini-golf, and enjoy swimming or skiing when in season. The resort also has craft workshops and special programs for children throughout the year.
What are some of the best things to do in Wintergreen Resort?
Wintergreen Resort has mountain hiking, golf, skiing during winter months, and scenic chairlift rides. Spa experiences, seasonal events, and outdoor dining are also frequently suggested for a well-rounded visit.
How is the weather in Wintergreen Resort?
Wintergreen Resort experiences cool winters around 28–44°F (-2–6°C), and warmer summers near 68–84°F (20–29°C). Spring and autumn are milder, with occasional rainfall and comfortable temperatures.
When is the best time to visit Wintergreen Resort?
Late spring through early autumn is often recommended for hiking, golf, and festivals, while winter draws visitors for skiing and snowboarding. Fall colors and spring blooms offer distinct scenic experiences.
What are the best places to visit in Wintergreen Resort?
Explore the mountain overlooks, nature trails, and the adventure park around Wintergreen Resort. The spa and golf course are also frequently suggested spots for relaxation and recreation.
What are some hiking trails in Wintergreen Resort?
Wintergreen Resort has mountain trails that wind through forested areas and feature scenic outlooks. The Lake Monocan Trail is frequently suggested for gentle walks, while other paths around the resort offer options for varying skill levels.
What are some family activities we can do in Wintergreen Resort?
Families can enjoy swimming, biking, hiking, and mini-golf at Wintergreen Resort. Seasonal programs, craft workshops, and nature exploration are regularly available for all ages.
What are some of the best day trip ideas from Wintergreen Resort?
Plan a visit to nearby vineyards, explore historic towns, or hike in the surrounding Blue Ridge Mountains. Local art galleries and farm markets are also frequently suggested for day trips.
Are there any pet friendly accommodations available in Wintergreen Resort?
Many vacation homes and condos around Wintergreen Resort are pet-friendly, welcoming dogs and other companions. Look for pet-inclusive stays and check for local trails that allow leashed pets.
What are some local tips for visiting Wintergreen Resort?
Pack layers for changing mountain weather and bring sturdy footwear for outdoor activities. Locals suggest booking activities in advance during busy seasons and exploring both forested and open areas for different views.
What is Wintergreen Resort known for?
Wintergreen Resort is known for its mountain recreation, including skiing, snowboarding, hiking, and golf. The area features forested landscapes, scenic overlooks, and family-friendly seasonal events.
What are the best hidden gems to explore in Wintergreen Resort?
Explore lesser-known forest trails, small waterfalls, and quiet picnic spots nestled around Wintergreen Resort. Locally owned art studios and workshops also provide creative experiences beyond the main attractions.
What are the best foods to try in Wintergreen Resort?
Enjoy locally inspired dishes like mountain trout, farm-fresh salads, and seasonal berry desserts at resort restaurants. Virginia wines and regional craft beers are frequently suggested for pairing with meals.
What should I bring for a trip to Wintergreen Resort?
Pack comfortable, weather-appropriate clothing, layered for cooler mornings and warmer afternoons. Bring sturdy shoes for hiking, sunscreen, and swimwear if you plan to enjoy pools or lakes.
What is the nightlife in Wintergreen Resort like?
Wintergreen Resort has relaxed nightlife, including casual bars, lounge areas, and occasional live music events at local venues. Evenings can include outdoor patios or social gatherings around fire pits.
What are the most popular events or festivals in Wintergreen Resort?
Wintergreen Resort hosts music festivals in summer, family-friendly celebrations during holiday weekends, and wine or food tastings throughout the year. Seasonal events draw visitors for mountain activities and outdoor entertainment.
Are there family friendly vacation rentals in Wintergreen Resort?
Wintergreen Resort has many vacation rentals suitable for families, including condos, mountain cottages, and spacious homes. These often feature kitchens, easy access to attractions, and amenities for children.
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- Shenandoah National Park
- University of Virginia
- Early Mountain Winery
- Wintergreen Resort
- Monticello
- Devils Backbone Brewing Co Basecamp
- James Madison University
- Glass House Winery
- Cardinal Point Winery
- Natural Bridge State Park
- Blenheim Vineyards
- Virginia Horse Center
- The Rotunda
- Liberty Mountain Snowflex Centre
- Downtown Mall
- Frontier Culture Museum
- John Paul Jones Arena
- James Monroe's Highland
- Amazement Square
- White Oak Lavender Farm & The Purple WOLF Vineyard
- Grand Caverns
- IX Art Park
- James River State Park
- White Lotus Eco Spa Retreat