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Holiday houses in Wintergreen Resort

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Quick stats about holiday rentals in Wintergreen Resort

  • Total holiday rentals

    Explore 730 holiday rentals in Wintergreen Resort

  • Nightly prices starting at

    Wintergreen Resort holiday rentals start at $119 NZD per night before taxes and fees

  • Verified guest reviews

    Over 28,490 verified reviews to help you choose

  • Family-friendly holiday rentals

    560 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 250 rentals that welcome pets

  • Holiday rentals with a pool

    480 properties feature pools

  • Rentals with dedicated workspaces

    240 properties have a dedicated workspace

  • Wi-Fi availability

    730 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.

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Top Guest favourite
A welcoming living area features two leather couches arranged around a wooden coffee table, which is complemented by a patterned rug. Large windows allow natural light to illuminate the space, offering views of the surrounding trees. Sliding glass doors provide access to an outdoor deck.
Home in Wintergreen Resort
4.99 out of 5 average rating, 175 reviews

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.

Top Guest favourite
The cabin's exterior is surrounded by lush greenery, featuring a spacious porch with seating and a hot tub nearby. The two-story structure is constructed of wood, with large windows allowing natural light to fill the interior. A picnic table is located in the yard.
Holiday home in Lovingston
4.96 out of 5 average rating, 271 reviews

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!

Top Guest favourite
A spacious bedroom features a high, wood-beamed ceiling and a large window providing natural light. The bed is dressed in navy bedding with a plaid blanket draped across it. A wooden dresser and lamp complement the rustic decor, and a mounted TV is positioned above.
Home in Wintergreen Resort
4.97 out of 5 average rating, 237 reviews

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.

Top Guest favourite
A spacious living area is highlighted by large floor-to-ceiling windows, offering views of the surrounding trees. A comfortable gray sofa and a round glass coffee table are present, along with a wooden dining table that seats six. An electric fireplace adds warmth to the space.
Villa in Wintergreen Resort
4.96 out of 5 average rating, 146 reviews

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!

Top Guest favourite
The living area features large sliding glass doors that open to a stunning view of the mountains. A modern dining table is positioned nearby, illuminated by a pendant light. Comfortable seating is arranged around the room, enhancing the inviting atmosphere.
Condo in Wintergreen Resort
4.98 out of 5 average rating, 129 reviews

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!

Guest favourite
The living area features a comfortable sectional sofa and a wooden coffee table, with a visible fireplace centrally located. Large windows provide natural light and views of the outdoor space. A mounted television is positioned above the fireplace, complementing the cozy ambiance.
Apartment in Wintergreen Resort
4.85 out of 5 average rating, 106 reviews

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!

Top Guest favourite
A bright and airy living area is highlighted by large windows offering mountain views. A casual seating arrangement features a light-colored sofa and a wooden dining table surrounded by black chairs. Sliding glass doors provide access to an outdoor deck.
Apartment in Rockfish
4.98 out of 5 average rating, 228 reviews

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.

Top Guest favourite
Home in Wintergreen Resort
4.97 out of 5 average rating, 126 reviews

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.

Superhost
A private furnished patio features a cozy seating area with light-colored cushions on a dark frame sofa. A wooden coffee table sits in front, accented by a woven rug. The surrounding greenery adds a natural backdrop, creating a peaceful setting for relaxation.
Condo in Wintergreen Resort
4.92 out of 5 average rating, 213 reviews

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.

Top Guest favourite
Cabin in Vesuvius
4.99 out of 5 average rating, 374 reviews

The Sanctuary

Nature lovers paradise! Named "The Sanctuary" for the place you can UNPLUG, unwind & find your peace! Perched up high on nearly 60 acres- you are sure to get fresh air & the rest you are searching for! Only 4 miles to Wintergreen, 6 miles to Sherando lake and backs up to the Blue Ridge Parkway there are plenty of things to do OR just relax and enjoy the crickets & stars! With crazy careers, growing kids & constant hustle- everyone needs a hide out like this every now and then!

Guest favourite
A cozy living area features a teal sofa with a yellow accent pillow and a light wood coffee table. The kitchen is adjacent, showcasing modern appliances. Stairs lead to the loft bedroom. Artwork hangs on the wall, and natural light enters through high windows.
Condo in Wintergreen Resort
4.95 out of 5 average rating, 176 reviews

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!

Top Guest favourite
The main living area features a local stone fireplace framed by large windows that allow natural light to fill the space. A comfortable couch and wooden coffee table create a welcoming atmosphere, complemented by decorative pillows and a small potted plant on the table.
Chalet in Wintergreen Resort
4.92 out of 5 average rating, 129 reviews

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

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Wintergreen Resort's top sights

Wintergreen Resort

285 locals recommend

The Market

109 locals recommend

The Plunge Snow Tubing Park

43 locals recommend

Other great holiday rentals in Wintergreen Resort

Top Guest favourite
Home in Wintergreen Resort
5 out of 5 average rating, 32 reviews

Best Blue Ridge Views at Sunrise over Wintergreen

Top Guest favourite
An open floor plan features wood flooring and large windows that allow light to fill the space. A cozy seating area includes a comfortable armchair and a low table, with a wood-burning stove beside a stone wall. The kitchen area is visible with modern appliances.
Treehouse in Roseland
4.93 out of 5 average rating, 85 reviews

Blue Ridge Treehouse

Top Guest favourite
A spacious living area features a corner fireplace with stacked logs, surrounded by a sectional sofa adorned with patterned upholstery. Large windows provide natural light, while a dark wood coffee table and a neutral-toned area rug enhance the inviting ambiance.
Townhouse in Wintergreen Resort
5 out of 5 average rating, 66 reviews

Beary Lazy - 4 beds and 2 sleeping sofas!

Top Guest favourite
A spacious living area features large windows that provide expansive views of the surrounding landscape. Comfortable seating includes a sectional couch and a reclining chair, arranged around a wooden coffee table. A sleek stone fireplace and a mounted television add to the contemporary decor.
Condo in Wintergreen Resort
4.96 out of 5 average rating, 52 reviews

Wintergreen Mountain Views - Diamond in the Slopes

Top Guest favourite
A wooden walkway leads to the entrance of the house, framed by vibrant pink rhododendron flowers. Tall trees provide a natural backdrop, with dappled sunlight filtering through the leaves, creating a serene outdoor setting.
Home in Wintergreen Resort
4.95 out of 5 average rating, 164 reviews

Bear's Mountain Escape

Guest favourite
Condo in Wintergreen Resort
4.9 out of 5 average rating, 61 reviews

Mountain View Vista: Resort Condo w/ Views

Guest favourite
Townhouse in Wintergreen Resort
4.9 out of 5 average rating, 84 reviews

Cozy condo with loft. Walk to Wintergreen resort!

Guest favourite
Condo in Wintergreen Resort
4.91 out of 5 average rating, 165 reviews

Cozy Comfort with a View - Wintergreen Resort

When is the best time to visit Wintergreen Resort?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$483 NZD$468 NZD$352 NZD$305 NZD$317 NZD$300 NZD$310 NZD$301 NZD$300 NZD$359 NZD$363 NZD$449 NZD
Avg. temp2°C4°C8°C14°C18°C22°C24°C23°C20°C14°C9°C4°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.

Destinations to explore