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Holiday rentals in Wintergreen

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Top-rated holiday rentals in Wintergreen

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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, 176 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.

FamilyLocationWifi

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, 238 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.

ValueFamilyHiking

Top guest favourite
The gravel pathway leads to a charming log cabin, framed by tall trees and surrounded by greenery. A sign reading 'COZY MOUNTAIN CABIN' is positioned near the path, inviting visitors to explore this secluded retreat in the Blue Ridge.
Cabin in Roseland
4.96 out of 5 average rating, 768 reviews

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.

LocationValueCondition

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!

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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.
Flat in Wintergreen Resort
4.85 out of 5 average rating, 107 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!

ValueLocationQuiet

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.
Flat 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.

ValueFamilySolo travel

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.
Apartment 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.

ValueLocationWifi

Top guest favourite
Home in Wintergreen Resort
4.97 out of 5 average rating, 127 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.

LocationFamilyWalkability

Guest favourite
A spacious outdoor deck features a round dining table surrounded by tall chairs, complemented by a striped couch with soft cushions. An umbrella provides shade, while the scenic mountain views extend into the distance, above a layer of mist.
Apartment in Wintergreen Resort
4.93 out of 5 average rating, 195 reviews

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!

ValueFamilyHospitality

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!

LocationValueHospitality

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.
Apartment in Wintergreen Resort
4.95 out of 5 average rating, 177 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!

LocationFamilyCheck-in

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, 130 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

FamilyValueView

Popular amenities for Wintergreen holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Wintergreen

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

ValueFamilyBack garden

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

Cozy Comfort with a View - Wintergreen Resort

ValueLocationNearby

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.
Apartment in Wintergreen Resort
4.98 out of 5 average rating, 131 reviews

Luxury Condo in the Sky! Finest in Wintergreen!

ValueLocationKitchen

Guest favourite
An open living and dining area showcases warm wooden walls and a colorful area rug. A comfortable seating arrangement includes a sofa with pillows and a coffee table, while a dining table with white chairs is positioned nearby. Large windows allow natural light to fill the space.
Home in Wintergreen Resort
4.95 out of 5 average rating, 239 reviews

Saltbox at Wintergreen, a Modern Mountain Escape

LocationValueSkiing

Guest favourite
The cabin is nestled among lush green trees, showcasing a multi-level structure with wooden balconies and a roof. A warm sunset casts a colorful glow over the exterior, highlighting its welcoming design and natural surroundings.
Cabin in Wintergreen Resort
4.97 out of 5 average rating, 118 reviews

3 Levels · 3 Scenic Decks · Game Room · Hot Tub

ValueFamilyDecor

Top guest favourite
Home in Wintergreen Resort
5.0 out of 5 average rating, 34 reviews

Best Blue Ridge Views at Sunrise over Wintergreen

ValueLocationView

Top guest favourite
Cottage in Nelson County
5.0 out of 5 average rating, 25 reviews

Starlit Soak – Romantic Hideaway in the Hollow

LocationQuietHot tub

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
5.0 out of 5 average rating, 66 reviews

Beary Lazy - 4 beds and 2 sleeping sofas!

LocationFamilyCheck-in

Frequently Asked Questions

  • What are the best places to stay in Wintergreen?

    Stay in mountain-view vacation homes, condos, or cottages near recreational areas. Properties around Wintergreen’s main resort area often feature amenities like pools, access to trails, and terraces.

  • What are the best things to do in Wintergreen with kids?

    Kids can enjoy outdoor adventure programs, guided nature walks, and swimming in resort pools. In winter, snow tubing and beginner ski lessons are often recommended activities for families.

  • What are some of the best things to do in Wintergreen?

    Explore hiking trails, enjoy skiing or snowboarding in cooler months, and play golf in warmer seasons. Visiting local breweries, shops, and participating in mountain festivals is frequently suggested.

  • How is the weather in Wintergreen?

    Wintergreen has cool winters around 28–44°F (-2–6°C), and warm, humid summers reaching 68–84°F (20–29°C). Rainfall is spread throughout the year, so a waterproof layer is often useful for outdoor plans.

  • When is the best time to visit Wintergreen?

    Mid spring through early fall is often recommended for mild temperatures and vibrant mountain scenery. If you enjoy winter sports, colder months bring snowfall and opportunities for skiing or snowboarding.

  • What are the best places to visit in Wintergreen?

    Wintergreen has scenic overlooks, mountain hiking trails, and golf courses that attract visitors. Local breweries and shops add to the experience, especially around the main resort area.

  • What are some hiking trails in Wintergreen?

    Explore forested trails with mountain views; paths around the main resort area frequently offer scenic overlooks and waterfalls. Trail networks cater to a range of abilities, from gentle walks to steeper climbs.

  • What are some family activities we can do in Wintergreen?

    Families can explore nature trails, play mini golf, or participate in outdoor adventure programs. Seasonal activities include snow tubing in winter, swimming in warmer months, and craft workshops around local festivals.

  • What are some of the best day trip ideas from Wintergreen?

    Popular day trips include exploring nearby vineyards, visiting small mountain towns with craft galleries, or hiking in regional parks. Local farm tours and river kayaking are frequently suggested for adventure seekers.

  • Are there any pet friendly accommodations available in Wintergreen?

    Several accommodations in Wintergreen welcome pets, often around the main resort and near hiking areas. Outdoor amenities and easy access to trails make it convenient to travel with your dog.

  • What are some local tips for visiting Wintergreen?

    Bring layers for changing weather and plan ahead for outdoor activities, especially in peak seasons. Locals suggest visiting mountain overlooks early in the morning for quiet scenery, and sampling craft food at neighborhood markets.

  • What is Wintergreen known for?

    Wintergreen is known for scenic mountain landscapes, outdoor recreation like hiking and skiing, and golf courses. Locally rooted food and craft beverages are frequently suggested throughout the area.

  • What are the best hidden gems to explore in Wintergreen?

    Discover tucked-away hiking paths, local artisan shops, and quiet picnic spots around the mountain. Insider tips often highlight farm-to-table dining and scenic overlooks that are less traveled.

  • What are the best foods to try in Wintergreen?

    Wintergreen’s dining features locally sourced mountain cuisine, including roasted meats, farm-fresh vegetables, and craft beverages. Seasonal menus often highlight apple desserts, regional cheeses, and handmade breads.

  • What should I bring for a trip to Wintergreen?

    Pack layers for changing mountain conditions, comfortable hiking shoes, and a waterproof jacket. If visiting during cooler months, bring warmer clothing; in summer, sunscreen and a hat help for outdoor activities.

  • What is the nightlife in Wintergreen like?

    Wintergreen’s nightlife centers on casual venues with music, craft beverages, and locally rooted dining. Social gatherings often feature scenic mountain views and relaxed atmospheres.

  • What are the most popular events or festivals in Wintergreen?

    Wintergreen has seasonal festivals, including events for music, arts, and food. Outdoor celebrations around Labor Day weekend and winter gatherings with snow sports are frequently suggested.

  • Are there family friendly vacation rentals in Wintergreen?

    Many vacation rentals in Wintergreen are equipped for families, often featuring spacious layouts, kitchen access, and outdoor amenities. Look for options near recreational areas and trails for easy access to activities.

Destinations to explore