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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, 174 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
A balcony is featured, showcasing two Adirondack-style chairs positioned for optimal mountain views. Sunrise illuminates the expansive horizon, with soft light reflecting off the distant landscapes. The floor is made of wood, enhancing the outdoor ambiance.
Flat in Wintergreen Resort
4.99 out of 5 average rating, 123 reviews

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!

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, 232 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
The unique octagonal house is framed by lush greenery, showcasing its distinctive architecture. A spacious deck offers a vantage point for enjoying unobstructed views of the surrounding landscape. Panoramic windows reflect the natural beauty of the Blue Ridge Mountains, inviting light into the living space.
Home in Afton
4.99 out of 5 average rating, 103 reviews

Mountain Overlook House - Blue Ridge Parkway

Unique octagonal house with stunning views of the Blue Ridge Mountains of Virginia. Located 2 miles from I-64, 15 minutes to downtown Waynesboro and an easy 25 min drive to Charlottesville and UVA. Open floor plan, perfect for gathering, and long-range 180 degree views from nearly every room. Fully equipped renovated kitchen. Quality linens and bedding. Rustic, yet modern decor. Home features large fireplace, outside fire pit, wifi, and board games galore. Stargazing and birdwatching heaven.

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, 127 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.
Flat in Wintergreen Resort
4.85 out of 5 average rating, 102 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.
Flat in Rockfish
4.98 out of 5 average rating, 225 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, 123 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.
Apartment in Wintergreen Resort
4.93 out of 5 average rating, 204 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.

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
4.94 out of 5 average rating, 188 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!

Top guest favourite
Cabin in Vesuvius
4.99 out of 5 average rating, 372 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!

Top guest favourite
A glass of white wine is positioned in the foreground, capturing the warm hues of a sunset. The sun's golden rays reflect off the wine, while silhouettes of trees and distant mountains create a tranquil backdrop in the evening sky.
Apartment in Wintergreen Resort
4.99 out of 5 average rating, 272 reviews

Panoramic Sunsets Mountain Views Pool $99 Midweek

SUMMER SPECIAL! Stay 2 nights and get your 3rd night for just $99 when you check in Sunday–Wednesday (select stays, next 60 days). Escape the summer heat and enjoy cooler mountain temperatures, central A/C, a heated outdoor pool, breathtaking sunset views, and two king suites with private en-suite bathrooms. Summer dates are filling fast—book now and experience one of Wintergreen's most sought-after mountain-view condos.

Popular amenities for Wintergreen holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Wintergreen

Top guest favourite
Home in Wintergreen Resort
5 out of 5 average rating, 27 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, 83 reviews

Blue Ridge Treehouse

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, 127 reviews

Cozy Cabin+Walk to Ski *Hot Tub* Mtn Vibe

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.
Apartment in Wintergreen Resort
4.96 out of 5 average rating, 49 reviews

Wintergreen Mountain Views - Diamond in the Slopes

Top guest favourite
Home in Wintergreen Resort
5 out of 5 average rating, 37 reviews

White Wolf Chalet at Wintergreen

Guest favourite
An expansive outdoor deck features a dining table with seating for six, along with several lounge chairs. A grill is positioned nearby, and the area is illuminated by a patio heater. Large windows provide views into the interior of the home.
Home in Wintergreen Resort
4.99 out of 5 average rating, 80 reviews

Hot Tub Valley View Pool Tennis Dogs OK EV Charger

Superhost
A cozy living area features natural stone accents around a wood-burning fireplace. A small dining table with two chairs is positioned near large windows, allowing ample natural light. Green accent walls enhance the inviting atmosphere, while a comfortable seating area is visible nearby.
Apartment in Wintergreen Resort
4.89 out of 5 average rating, 218 reviews

Tips Up: Cozy Slopeside Retreat w/ Fireplace

Top guest favourite
A spacious deck offers a wooden dining table set for eight, accompanied by a cozy bench. A Big Green Egg grill sits nearby, surrounded by trees and mountains. The scene reflects a tranquil outdoor setting, ideal for enjoying meals or gatherings amidst nature.
Chalet in Wintergreen Resort
5 out of 5 average rating, 87 reviews

Mountain Views, Hiking, Ski-Out @ Tyro

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

  1. Airbnb
  2. United States
  3. Virginia
  4. Nelson County
  5. Wintergreen