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Holiday houses in Wintergreen

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Top-rated holiday rentals in Wintergreen

Guests agree: these stays are highly rated for location, cleanliness and more.

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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, 233 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 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, 762 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.

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, 142 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
A cozy living area features a brown sofa and an armchair in muted blue. A wooden coffee table sits atop a light brown rug, with a lamp illuminating one corner. Framed artwork adorns the walls, while a storage cabinet offers practical space.
Condo in Wintergreen Resort
4.94 out of 5 average rating, 165 reviews

Cozy Updated Wintergreen Condo at Devil’s Knob

This 2 bedroom, 2 bathroom, fully updated condo is a great place to spend your get away at Wintergreen. Fantastic wifi throughout. Brand new queen mattress in master bedroom. Enjoy Apple TVs in the living room and bedrooms. Sony 55” tv with soundbar and subwoofer in living room. Mounted big screen tv in the master bedroom. NES classic and Nintendo Switch dock. On the deck is a Weber electric grill. Nest thermostat. We hope you will enjoy this fully loaded home away from home as much as we do!!

Top Guest favourite
The living room features vaulted ceilings and large windows offering expansive mountain views. A comfortable seating area is arranged around a wooden coffee table, with a cozy wood-burning fireplace to one side. Soft lighting is provided by two lamps, enhancing the inviting ambiance.
Townhouse in Wintergreen Resort
4.98 out of 5 average rating, 105 reviews

Hike*Spacious MtnTop Escape *4 EnSuites* Dogs OK

Enter this recently renovated home and discover an open floor plan on the main level with endless views of Shenandoah Valley! Highlights include: ✶ Easy Access to breweries! ✶ Spectacular Mountain Top views! ✶ Recently Renovated! ✶ Every bedroom has an en-suite bath! ✶ Helix Hospitality Mattresses! ✶ 3 Roku TVs! ✶ Cozy wood-burning fireplace! ✶ Hiking! Bring the family or a large group and enjoy the common space for gathering & another 3 floors of bedrooms to spread out and enjoy privacy.

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, 104 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.

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, 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.
Apartment in Rockfish
4.98 out of 5 average rating, 226 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, 124 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
4.93 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.

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.
Condo 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.

Top Guest favourite
The exterior of a multi-level home is nestled among trees, with warm lighting illuminating the porch and deck. The spacious deck features a staircase leading down, surrounded by autumn leaves, creating a welcoming atmosphere.
Home in Wintergreen Resort
4.89 out of 5 average rating, 158 reviews

Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat

We invite you to enjoy Lily Pad, our family-friendly home located in the heart of Wintergreen Resort and perfect for all-season enjoyment. (Covid-CDC guideline cleaned.) On the 5th hole green of Devil’s Knob Golf Course. Walking distance to the APPALACHIAN TRAIL. Large paved driveway for 5-6 cars. This home is perfect for 3-5 couples, or two families with children or large/extended families.

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, 13 reviews

Mountain View | Hot tub | Sleeps 14

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
The airy living room features a stone gas fireplace beneath a large mounted TV, offering a cozy focal point. Large windows frame the view of the outdoors, allowing natural light to fill the space. Ample seating is provided by a sectional couch and accent chairs.
Home in Wintergreen Resort
4.96 out of 5 average rating, 51 reviews

Welcome to Winterhaven! 5BR/4BA .5mi from lodge!

Guest favourite
An inviting open living space features large windows that allow natural light to fill the room, showcasing scenic mountain views. The wooden walls and flooring create warmth, while a mix of seating options can be seen. A dining table is placed near the kitchen area.
Cabin in Wintergreen Resort
4.85 out of 5 average rating, 46 reviews

Historic Cabin Hot Tub Mntn View Dogs OK King Bed

Top Guest favourite
An A-frame cabin is illuminated softly by string lights, showcasing a front deck that invites relaxation. Large windows reveal a warm interior, while the surrounding wooded lot creates a serene, natural setting at dusk.
Cabin in Wintergreen Resort
4.98 out of 5 average rating, 89 reviews

On The Rocks

Guest favourite
Home in Wintergreen Resort
4.93 out of 5 average rating, 82 reviews

Whispering Creek Hot Tub Pool TennisGolf King Beds

Top Guest favourite
Tent in Nellysford
4.99 out of 5 average rating, 94 reviews

Natural Living in a Bell Tent

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, 88 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