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, 153 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, 220 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, 121 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, 142 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, 224 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, 149 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 Escape | 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

4.96 out of 5 average rating, 372 reviews

A spacious living room features a prominent stone fireplace adorned with wildlife sculptures. Large windows allow natural light to fill the space, illuminating comfortable seating. An inviting sectional couch and wooden coffee table create a cozy gathering area, while art pieces enhance the room's character.

Home in Afton

FLASH SALE: Blue Ridge Estate Wine, Beer, & Skiing

Come for the views, stay for the vibes. Designed for easy weekends with friends, good laughs, and zero rushing. Tucked into the Blue Ridge Mountains, you’re minutes from scenic drives, breweries, and wineries—then back home to spread out, unwind, and keep the good times going. Perfect for laid-back group getaways that mix nature by day and great drinks by night. Boogie Nights Manor a wildly spacious, 4,000+-sqft home where every room is a feast for the eyes, filled with art and artifacts.

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, 112 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, 235 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, 118 reviews

Cliffs Edge -A Contemporary Home, Spring Skiing!

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.

4.98 out of 5 average rating, 141 reviews

The exterior view showcases a modern blue house set against a backdrop of lush green hills. A wooden deck extends from the home, providing access to outdoor space. The gravel driveway is lined with a rustic split-rail fence, enhancing the natural feel of the surroundings.

Home in Nellysford

Llama Loft | Fire Pit | Fenced Yard | Nelson 151

Escape to a spacious, colorful home off the Brew Ridge Trail with oversized windows, mountain views, and plenty of room for groups or couples. Cook in a stocked kitchen, then relax by the fire pit or grill out and unwind on the deck while the dogs enjoy the fenced in yard. Accessible bedrooms and bathrooms on the main floor make it easy for everyone to enjoy. Perfectly located near Wintergreen Resort, Skyline Drive, breweries, wineries, vineyards, hiking, biking, and golf.

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, 134 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!

Popular amenities for house rentals in Wintergreen Resort

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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, 47 reviews

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, 230 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, 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

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, 35 reviews

Perfect House

5 out of 5 average rating, 15 reviews

Hilltop Hideaway - Wintergreen 5BR with Hot Tub

4.95 out of 5 average rating, 41 reviews

Walk to Ski Slopes | EV Charger | Views | Hot Tub

A modern mountain home is showcased amidst a snowy landscape, surrounded by trees. A deck extends from the front entrance, providing views of the valley below. Soft white snow covers the ground, complementing the neutral tones of the house.

4.82 out of 5 average rating, 125 reviews

5 min toSki! Mntn View HotTub Pool Table MovieRoom

Weekly house rentals

4.95 out of 5 average rating, 42 reviews

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.

Home in Roseland

Hot Tub! Wintergreen Resort!

4.98 out of 5 average rating, 60 reviews

A modern guesthouse showcases a sloped roof and wooden accents, surrounded by lush green grass. Expansive glass doors offer views of the interior, while a well-defined stone pathway leads to the entrance. The property is set against a backdrop of rolling hills and trees.

Home in Crozet

Orso Blu one-of-a-kind VIEWS in Crozet

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, 47 reviews

Forest Cabin Getaway: Hike, Soak, Play

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, 50 reviews

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

A spacious house is set amidst a serene winter landscape, surrounded by trees and blanketed in snow. The wooden deck extends around the house, offering ample outdoor space. Large windows allow for natural light, enhancing the connection with the surrounding nature.

4.92 out of 5 average rating, 75 reviews

4 min to Ski: Whispering Creek Hot Tub King Beds

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, 69 reviews

Panorama Peak Lodge-4 bedroom with sweeping views

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, 35 reviews

Ridge Retreat @ Wintergreen!

4.96 out of 5 average rating, 26 reviews

The spacious living area features high vaulted ceilings with wooden beams and large windows allowing natural light to fill the space. A comfortable leather sofa is positioned near a coffee table, while a dining area with black chairs is visible in the background. A stone fireplace adds a cozy focal point.

Home in Nellysford

Charming Wintergreen resort home

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, 51 reviews

Stunning Views, Hot Tub, Impeccable Design

A spacious living area is highlighted by a soaring stone fireplace and large windows allowing natural light to filter in. Comfortable seating arrangements are present, complemented by vibrant artwork on the walls. A warm wooden floor adds a cozy touch to the inviting atmosphere.

4.94 out of 5 average rating, 33 reviews

Bluebird Mtn Home ~Dog Friendly ~ ~No step entry~

The exterior of a two-story house is shown, featuring a combination of stone and wood paneling. Surrounding trees provide natural shade. A set of steps leads to the entrance, which is framed by a covered porch. A pathway and deck are visible on the side.

5 out of 5 average rating, 22 reviews

Mountain View Charm

A two-story mountain home is surrounded by a wooded landscape, showcasing a large front deck supported by wooden beams. The exterior features light-colored siding and stone accents, with a gravel pathway leading to the entrance.

5 out of 5 average rating, 33 reviews

White Wolf Chalet at Wintergreen

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

5 out of 5 average rating, 49 reviews

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.

Home in Roseland

Wintergreen Mountain Retreat

4.86 out of 5 average rating, 42 reviews

A cozy living area is presented with a large sectional sofa in rich brown tones, complemented by a light-toned accent chair. A flat-screen television is mounted above a modern stone fireplace. Natural light filters through blinds on the windows, enhancing the warm ambiance.

Home in Roseland

Mountain retreat with hot tub