House holiday rentals in Wintergreen Resort

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.

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.

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.

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.

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.

4.95 out of 5 average rating, 163 reviews

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.

4.99 out of 5 average rating, 106 reviews

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

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.

Superhost

A spacious living area features a large sectional sofa adorned with colorful throw pillows. High, wooden ceilings are complemented by large windows that bring in natural light. A dining table and rustic décor are visible, creating a comfortable gathering space.

4.84 out of 5 average rating, 141 reviews

Hot Tub EV Charger Pool Table Dogs OK Tennis Golf

Sweeping views year round. Retreats, romantic weekends or adventurous getaways. Close to wineries, breweries, farmers market, and walking distance to hiking trails. Sleeps 16: K, K, Q, 2 DBL,4 twin, 1PO 🏡 2-Story vaulted ceiling, gas fireplace, 60" TV 🛁 HOT TUB 🔋 EV charger 🔊 Sound system 🍽️ Dining table for 6 + breakfast bar 💻 Workspace w/ FAST Wi-Fi 🎱 Game room: shuffleboard, pool table Seasonal pool/tennis. Resort access not included. Pet fee $187. 8min walk or 3min drive to ski.

4.98 out of 5 average rating, 132 reviews

Stargaze on 12 Acres: Hot Tub 55"TV Fire Pit Grill

Relax with the family on 12 private acres at our peaceful, brand new construction farmhouse. We're just 12 miles to Wintergreen Ski Resort and Stoney Creek Golf, breweries, and wineries. Sleeps 8: K, K, Q + daybed w/ trundle. ★Amazing mountain views ★Hot tub for 6 people ★Outdoor shower ★Rockers, Adirondacks chairs for idle stargazing ★Gas grill ★Teak dining table seats 6 ★Indoor/outdoor gas fireplaces ★View 55” TV from comfy leather sofa/kitchen ★Pack 'n Play/Bassinet/High chair ★Mud room

5 out of 5 average rating, 238 reviews

Home in Greenwood

Gorgeous Modern Mountain Home + Blue Ridge Views

GREENWOOD VISTA - Escape to our modern mountain home nestled along the Blue Ridge mountains. Whether you want to explore Shenandoah National Park, visit wineries, or relax in our hot tub with stunning mountain views, this gorgeous A-Frame home is the perfect place for you. We have thoughtfully appointed our home with everything you need to be comfortable. From a luxurious bedroom suite, fully equipped kitchen, to coffee and wet bar, sauna, outdoor grill, billiard table, and a cozy fire pit.

A spacious living area features a stone fireplace as the focal point, framed by large windows that offer views of the surrounding trees. A comfortable sectional sofa is arranged around a coffee table, with a television positioned on a media console to the side.

4.97 out of 5 average rating, 119 reviews

Cozy 5-bedroom home for large gatherings.

Within the Wintergreen Resort, this 4-season mountain home is perfect for a large gathering with friends and family. A generously stocked home for all your needs and occasions. A clean, comfortable, and relaxing home with many amenities and accessible to many outdoor adventures. Wintergreen Resort provides a great skiing experience. Being near the scenic Blue Ridge Parkway, Skyline Drive and the Appalachian Trail, you will wish to return every season to get away from your busy schedules.

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.

4.95 out of 5 average rating, 239 reviews

Saltbox at Wintergreen, a Modern Mountain Escape

Your mountain adventure awaits at Saltbox, an inviting, eclectic home at Wintergreen Resort in the Blue Ridge Mountains. Combining modern and vintage decor, plus original art, Saltbox was designed to provide escape, inspiration and fun. Nestled at the end of a quiet cul-de-sac drive, with beautiful woods to explore, it's just seconds from the Resort (skiing, tubing, hiking, dining, spa, outdoor movies and more)! Saltbox is the perfect home base for your next getaway, any time of year!

4.97 out of 5 average rating, 125 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.

A cozy living space is highlighted by large windows that provide views of the surrounding trees. A comfortable sofa and armchair are arranged around a glass coffee table, complemented by a wooden dining set nearby. Warm wood accents are present in the ceiling beams and furnishings.

4.81 out of 5 average rating, 137 reviews

Cozy Mountain Home Nestled in Nature!

4 bedroom/2.5 bath home nestled in the Blue Ridge Mountains at Wintergreen Resort. This will be your favorite home away from home. Enjoy all the creature comforts while basking in all that nature has to offer. First floor master bedroom w/ private bathroom featuring a whirlpool tub . Two bedrooms upstairs with shared bathroom. Common space with large wood burning fireplace, full kitchen amenities, and high capacity washer/dryer. Outdoor deck with table and gas grill!

The exterior of the home is surrounded by lush trees, featuring a spacious deck that extends around the building. A gravel pathway leads to the front steps, creating a welcoming entrance. Natural light filters through the trees, enhancing the peaceful setting.

4.9 out of 5 average rating, 189 reviews

Wintergreen Resort: Weeping Rock Retreat

Welcome to Weeping Rock Retreat in Wintergreen Resort. This 4 bedroom, 3 full bath home is certain to fit your individual or family needs. Tucked away on a hill off a quiet street is sure to give you a peaceful retreat to enjoy your vacation. Our home is located walking distance from the Upper Shamokin Trail which features a great scenic waterfall and easy trail for family. Great for large or multiple families and a short drive to the ski slopes.

Popular amenities for Wintergreen Resort house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

An outdoor deck is equipped with a propane firepit surrounded by a dark block, offering a cozy gathering space. Comfortable, upholstered seating is arranged for relaxation, with expansive views of trees and hills in the background, showcasing the natural beauty of the mountainous landscape.

4.98 out of 5 average rating, 65 reviews

Stunning Views, Hot Tub, Impeccable Design

An outdoor deck features a cozy fire pit surrounded by comfortable seating. The scene is tranquil with trees in the background, and a colorful sunset sky enhances the atmosphere. Soft lighting along the railing adds a welcoming touch.

4.98 out of 5 average rating, 57 reviews

4.96 out of 5 average rating, 238 reviews

A private in-ground swimming pool is surrounded by a wooden deck and sun loungers. Shade is provided by a canopy, and lush greenery is visible in the background, highlighting the calming outdoor setting. The pool features a net for recreational activities.

Home in Lovingston

Private Pool Opens April 1 - All Year Hot Tub

4.94 out of 5 average rating, 159 reviews

A functional kitchen with wooden cabinetry and an island is featured. The space includes a stove, modern appliances, and a ceiling fan. A brick wood stove adds a rustic element, while a small plant sits on the island, providing a touch of greenery.

Home in Afton

Farmhouse on Working Vineyard

4.87 out of 5 average rating, 30 reviews

Mountain Home: Hot Tub, Game Room, Pets, King Beds

A living room area features a queen sofa bed, accented with decorative cushions. A small green side table is positioned beside a cozy armchair. A colorful area rug lays on the floor, and wall art depicting a serene forest scene adds visual interest. Natural light enters from a nearby window.

4.98 out of 5 average rating, 47 reviews

Perfect House

A spacious outdoor living area features a modern hot tub with glowing blue water, surrounded by a custom-built bar. Soft lighting from overhead lanterns adds a cozy ambiance, while a large screen TV is mounted nearby, overlooking the tranquil wooded surroundings.

5 out of 5 average rating, 64 reviews

Luxury Oasis | Hike, Lakes, Golf | Pet friendly!

5 out of 5 average rating, 29 reviews

Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14

Weekly house rentals

5 out of 5 average rating, 17 reviews

Mountain View | Hot tub | Sleeps 14

A deck area is shown, featuring comfortable seating arrangements and a coffee table. Lush greenery surrounds the space, with expansive views of the distant Blue Ridge Mountains under a clear blue sky, creating a serene outdoor retreat.

4.93 out of 5 average rating, 44 reviews

Wren Time

5 out of 5 average rating, 30 reviews

Best Blue Ridge Views at Sunrise over Wintergreen

A cozy living room is featured, showcasing a wooden ceiling and a fireplace. A deep blue sectional sofa is arranged around a coffee table. Natural light floods in through a door leading to the balcony, revealing views of the surrounding trees and winter landscape.

5 out of 5 average rating, 42 reviews

Premiere 2 BR Getaway Ski In/Out Wintergreen Condo

5 out of 5 average rating, 13 reviews

A spacious bedroom features a comfortable bed adorned with a dark blue quilt and white throw. Two bedside lamps are placed on wooden tables, and natural light is provided by large windows. A geometric rug covers the wooden floor beneath.

Home in Nelson County

Blue Bear

A spacious living area features a neutral color palette, with a large sectional sofa adorned with patterned cushions, a wooden coffee table at its center, and stylish accent chairs. High ceilings and large windows allow natural light to fill the space, enhancing the inviting atmosphere.

5 out of 5 average rating, 41 reviews

Ridge Retreat @ Wintergreen!

4.96 out of 5 average rating, 27 reviews

Cozy Wintergreen Townhome

4.96 out of 5 average rating, 28 reviews

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

Private house rentals

A warm and inviting living space features a stone fireplace with a fire glowing inside. A comfortable chair with patterned fabric sits beside a small glass coffee table. Natural light enters through large windows, creating a cozy atmosphere.

4.88 out of 5 average rating, 49 reviews

Hot Tub! Wintergreen Resort!

4.94 out of 5 average rating, 85 reviews

The Treehouse at Wintergreen

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.

4.96 out of 5 average rating, 51 reviews

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

4.97 out of 5 average rating, 32 reviews

Hilltop Hideaway - Wintergreen 5BR with Hot Tub

5 out of 5 average rating, 37 reviews

White Wolf Chalet at Wintergreen

The open living area showcases a high ceiling with a fan and large windows that allow natural light to fill the space. A dining area features a round table surrounded by chairs, while comfortable seating is arranged near a wooden accent wall. A stylish archway leads to an organized kitchen.

5 out of 5 average rating, 52 reviews

Wintergreen Mountain Retreat

A spacious great room features a stone fireplace as its focal point, surrounded by large windows that offer views of the sunset and surrounding trees. Leather couches and a glass coffee table complement the modern decor, while a plush ottoman provides extra seating.

4.94 out of 5 average rating, 72 reviews

Panorama Peak Lodge-4 bedroom with sweeping views

The outdoor deck showcases a six-person hot tub, with surrounding seating for relaxation. A stunning view of the mountains and trees with autumn foliage forms an inviting backdrop, enhancing the outdoor living experience.