House vacation 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, 150 reviews

Close to skiing! | 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, 216 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 modern living area features a sleek leather sectional sofa adorned with patterned cushions, accompanied by a wooden coffee table. Large windows offer views of the surrounding trees, while natural light enhances the inviting space. A floor lamp adds illumination next to the sofa.

4.96 out of 5 average rating, 120 reviews

Peaceful 3-BR Mountain home w/Fireplace + Hot tub

Charming 3-bedroom mountain retreat at the top of Wintergreen Resort. Peaceful and private location. Relax in front of the gas fireplace, soak in the hot tub, or sit on the deck and enjoy the views. Spend your day hiking a nearby trail and enjoy visiting local restaurants, breweries, and wineries. Kitchen is fully stocked and there is a new gas grill on deck. Kids will love the upstairs twin bedroom, complete with a play area with books & toys. Separate den with TV and workspace on lower level

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.

4.94 out of 5 average rating, 141 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.

5 out of 5 average rating, 223 reviews

Home in Greenwood

Gorgeous Modern Mountain Home + Blue Ridge Views

GREENWOOD VISTA - Escape to our modern mountain retreat 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.

4.99 out of 5 average rating, 134 reviews

An inviting outdoor space features a hot tub surrounded by a spacious deck, with mountain views in the background. A large dining table with wooden chairs is positioned indoors, complemented by a fully-equipped kitchen visible in the adjacent area. A cozy fire pit with adirondack chairs provides a warm setting.

Home in Afton

Hot Tub, Firepit, Mtn Views, Walk to Coffee & Park

Welcome to Creekside! Just minutes from the best wineries and breweries, it’s the perfect getaway to explore the 151 Brew Trail, Wintergreen Resort and the Blue Ridge Parkway. Enjoy mountain views and privacy in the hot tub. Roast marshmallows around the huge fire pit. Cozy up on the sectional sofa in front of the 65" 4K TV. Cooks will enjoy the spacious and fully equipped kitchen! All beds have premium memory foam mattresses. Fast Wi-Fi for remote work! Level 2 EV charger located in driveway.

4.99 out of 5 average rating, 148 reviews

A three-story wooden house is nestled among lush greenery in a forested setting. The deck and patio area are accessible, surrounded by trees and natural landscaping, creating a serene environment for relaxation.

Home in Nellysford

Cabin Retreat | Family & Dog Friendly | Fire Pit

Welcome to the Wooder House, a cozy haven nestled in the woods of Virginia's beautiful Nelson County! Enjoy relaxing and connecting in a private home centered on 38 wooded acres, but close to NelCo fun! - Peaceful nature escape - Outdoor fire pit & patio - Great for families & dogs - Fully stocked kitchen - Private trail + hiking options nearby - 8+ min. to wineries, breweries, cideries, restaurants - 25 min. to Wintergreen Resort For more photos and fun, check us out on IG: @thewooderhouse

4.97 out of 5 average rating, 108 reviews

Stargazing on 12 Acres: Hot Tub 55"TV Fire Pit

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

4.99 out of 5 average rating, 284 reviews

A charming cottage is positioned alongside a gently flowing trout stream, with a backdrop of lush greenery. Rocks line the water's edge, and a large, fenced yard surrounds the home, providing a peaceful setting. A red roof contrasts beautifully with the natural surroundings.

Home in Tyro

Bear Creek Inn 3 BR House Creekside

3BR HOUSE, QUIET CREEKSIDE RETREAT, PET FRIENDLY, FENCED YARD ENTIRE 3 BR mountain home with a large fenced backyard and a babbling creek—perfect for couples, families, and pets. Minutes to Crabtree Falls, the Appalachian Trail head, and George Washington National Forest. Unwind in nature, then explore Nelson 151 breweries and wineries or head to Wintergreen Resort just 12 miles away. Space, privacy, and adventure all in one unforgettable stay. Pet fee auto added when indicated at booking.

Superhost

An inviting exterior of a two-story home is presented, featuring a blend of wood and stone accents. Large glass windows provide natural light, and snow blankets the ground, creating a serene winter atmosphere. A sloped driveway leads to the entrance, surrounded by trees.

4.85 out of 5 average rating, 127 reviews

Walk to Ski! HotTub PoolTable Shuffleboard Dogs OK

8min walk or 3min drive to ski. Sweeping views year round. Retreats, romantic weekends or adventurous getaways. Close to wineries, breweries, farmers market, and walking distance to three great hiking trails. Sleeps 16: K, K, Q, 2 DBL,4 twin, 1PO ★Dogs OK ★2,714sqft ★HOT TUB for 7 ★Sound system ★2-Story vaulted ceiling, gas fireplace, 60"TV ★Dining table for 6 + breakfast bar ★Workspace w/ FAST Wi-Fi ★Shuffleboard ★Pool table Seasonal pool/tennis. Resort access not included. Pet fee $187.

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, 234 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, 117 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.

Popular amenities for Wintergreen Resort house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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.

4.96 out of 5 average rating, 111 reviews

Cozy 5-bedroom home for large gatherings.

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.

4.95 out of 5 average rating, 41 reviews

Hot Tub! Wintergreen Resort!

4.93 out of 5 average rating, 233 reviews

The exterior of Pine Lake Lodge is displayed, featuring a stone chimney and a covered porch with several chairs. Lush green grass surrounds the lodge, complemented by trees and colorful foliage in the background, creating a serene outdoor setting.

Home in Charlottesville

Pine Lake Lodge

4.96 out of 5 average rating, 229 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

Seasonal Private Pool - All Year Hot Tub

A spacious outdoor deck is surrounded by lush greenery, featuring a cozy seating area arranged around a fire pit. A private hot tub is visible on a raised platform, while the cabin showcases multiple levels of decks under a canopy of trees.

4.91 out of 5 average rating, 46 reviews

Forest Cabin Getaway: Hike, Soak, Play

4.94 out of 5 average rating, 154 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

The exterior of a modern mountain condo is showcased, featuring a wooden ramp leading to the entrance. The structure is framed by trees and includes triangular windows that complement the wood siding, creating a harmonious blend with the natural surroundings.

4.94 out of 5 average rating, 67 reviews

Wintergreen Condo~ 1 Minute To Four Seasons Resort

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.

4.97 out of 5 average rating, 34 reviews

Perfect House

Weekly house rentals

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, 41 reviews

Wren Time

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.

5 out of 5 average rating, 46 reviews

The living room features high ceilings with exposed beams and large windows showcasing the surrounding trees. A light gray sofa and armchairs provide comfortable seating, while a round coffee table sits at the center. A jute area rug adds texture to the hardwood floor.

4.95 out of 5 average rating, 60 reviews

Treeloft 17: Ski in/ski out – EV charger – 3BR/3BA

The farmhouse is surrounded by vibrant autumn foliage, with distant mountains rising in the background. The structure features a screened patio and a spacious yard, with trees and open fields visible, creating a serene natural setting.

4.99 out of 5 average rating, 72 reviews

Cozy Farmhouse W/Mountain Views

4.94 out of 5 average rating, 81 reviews

The Treehouse at Wintergreen

The living area features a central coffee table made of natural wood, surrounded by a light gray sectional sofa and two brown leather chairs. A stone fireplace serves as a focal point, with a mounted television above. Skylights above provide ample natural light.

5 out of 5 average rating, 18 reviews

Away from it ALL

The home is nestled among trees, showcasing a two-level structure with multiple decks. The warmth of wood accents is complemented by large windows that invite natural light. A peaceful, wooded landscape surrounds the property, offering a sense of privacy and tranquility.

4.99 out of 5 average rating, 81 reviews

Heart of Wintergreen, Hot Tub, Fireplace

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, 32 reviews

Ridge Retreat @ Wintergreen!

Private house rentals

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, 50 reviews

Stunning Views, Hot Tub, Impeccable Design

4.88 out of 5 average rating, 24 reviews

Mountain Views, Hot Tub, Impeccable Design

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, 52 reviews

Luxury Oasis|Family&Pets|Outdoor Lounge|Fire pit

5 out of 5 average rating, 58 reviews

A clear, winding river is surrounded by lush greenery and trees, reflecting the blue sky above. Sunlight dances on the water's surface, while the vibrant foliage frames the scene, creating a peaceful natural setting.

Home in Massies Mill

Country retreat w. mountain views + river access

The exterior of the house features a modern design with a combination of gray siding and a shingled roof. Surrounded by trees, the entryway is framed by steps leading to the front door, with a spacious driveway visible in the foreground.

4.9 out of 5 average rating, 59 reviews

Luxury House on Mountain Golf Course near Slopes

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, 48 reviews

Wintergreen Mountain Retreat

Superhost

4.91 out of 5 average rating, 77 reviews

Home in Wintergreen Resort 5BR/ 3 lvl