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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

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.

4.99 out of 5 average rating, 181 reviews
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

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.

4.97 out of 5 average rating, 238 reviews
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

Bear's Mountain Escape

Dog friendly, 3 BR, 2 BA, loft style condo located in the heart of the Wintergreen Resort. Ski check-in, restaurants, the mountaintop market, & The Mountain Inn are all right across the street! 2-story unit with a main floor primary BR & hall bath. Main floor bonus room with single & trundle. The loft contains 2 twin beds and the 2nd full bath. Parking, pool, washer/dryer, and Wi-Fi included. Fully stocked kitchen, wood burning fireplace, balcony, all towels/linens provided. Sleeps up to six.

4.95 out of 5 average rating, 170 reviews
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

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!

4.96 out of 5 average rating, 151 reviews
Top guest favourite
Home in Wintergreen Resort

Best Blue Ridge Views at Sunrise over Wintergreen

Spectacular Mountain Views & Sunrises Spend your days hiking over 30+ miles of trails (including the Appalachian Trail), driving the Blue Ridge Parkway, kayaking the lake in the summer, leaf peeping in the Fall, skiing one of the regions best mountains in the winter, or exploring Virginia's brewery and wine country. Whichever you choose, we're positive you'll enjoy your time at Sunrise over Wintergreen! New host family of beloved 250+ ★★★★★ 'Best View in the Blue Ridge from Biscuit's Porch'.

5.0 out of 5 average rating, 38 reviews
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

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!

4.98 out of 5 average rating, 134 reviews
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

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!

4.86 out of 5 average rating, 111 reviews
Top guest favourite
A scenic view of rolling hills is captured at sunset, with soft hues of orange, pink, and purple coloring the sky. In the foreground, a glass of clear liquid rests on a wooden railing, enhancing the tranquil atmosphere.
Apartment in Wintergreen Resort

3 BR 3 BA, 2 story condo in Highlands

Newly renovated condo! You can't beat the view from up here. Top floor/vaulted ceilings, next to the Highlands Lift. Just steps from the expert slopes and on the Wintergreen shuttle route. Enjoy hiking, skiing, snowboarding, tubing, outdoor pool time or a local brewery. This condo has 2 master's with king beds, 1 bunk bed (twin over full), a single twin bed and a pull out twin sleeper sofa. The king beds have new high quality mattresses and luxury bedding and a 60" HDTV in living room

4.99 out of 5 average rating, 185 reviews
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

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.

4.98 out of 5 average rating, 232 reviews
Top guest favourite
Home in Wintergreen Resort

Cliffs Edge - It’s Pumpkin Spice Time!

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.

4.97 out of 5 average rating, 130 reviews
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

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!

4.93 out of 5 average rating, 199 reviews
Guest favourite
Home in Wintergreen Resort

Designer Home w/ Incredible Views, Sleeps 16

Welcome to Highlands Overlook, a designer-decorated home in the heart of Wintergreen. The deck is second-to-none, complete with hot tub, cedar barrel sauna, fire table, dining for 10, grill, smoker, pizza oven, and views everywhere. The light-drenched interior is equally impressive. With 6 bedrooms plus a private game room with pullout sofa, the home sleeps 16 comfortably. Plus, pet friendly! Managed by Chris at New School Hosting- click on his profile below to see more reviews.

4.94 out of 5 average rating, 109 reviews

Popular amenities for Wintergreen holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Wintergreen

Top guest favourite
A balcony view reveals a vast expanse of rolling green mountains under a clear blue sky. A square table is surrounded by two woven chairs, inviting guests to enjoy the serene landscape of the Blue Ridge Mountains and Rockfish Valley.
Apartment in Wintergreen Resort

Condo with Valley Views!

4.93 out of 5 average rating, 40 reviews
Guest favourite
Home in Wintergreen Resort

Luxury|Hot Tub|Sauna|Cold Plunge|Game Room|Views

4.97 out of 5 average rating, 63 reviews
Guest favourite
Home in Wintergreen Resort

Mountain View | Hot tub | Sleeps 14

5.0 out of 5 average rating, 22 reviews
Guest favourite
Cabin in Wintergreen Resort

The Honey Den - Your WTG Fall Retreat! w/ Mtn Vs

5.0 out of 5 average rating, 11 reviews
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

Beary Lazy - 4 beds and 2 sleeping sofas!

5.0 out of 5 average rating, 66 reviews
Top guest favourite
A panoramic view of rolling mountains is displayed under a colorful sky during sunrise. Soft clouds hover over the lush green hills, creating a serene landscape. The vast expanse of nature invites tranquility and offers a sense of openness.
Flat in Wintergreen Resort

Panoramic Blue Ridge Views | dog friendly | pools!

4.96 out of 5 average rating, 25 reviews
Guest favourite
Apartment in Wintergreen Resort

Ski-in/out What-a-Mountain View Fireplace King Bed

4.94 out of 5 average rating, 53 reviews
Top guest favourite
Home in Wintergreen Resort

Art & Soul: Sauna/Hot Tub & EV Charger/Hammocks

4.97 out of 5 average rating, 30 reviews

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