House holiday rentals in Wintergreen Resort

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, 238 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.

LocationValueSleep quality

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, 181 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.

LocationFamilyCheckout

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.

4.83 out of 5 average rating, 142 reviews

5 min to Ski! MntnView Hot Tub PoolTable MovieRoom

5min drive to ski. Sweeping views year round. Contemporary décor with rustic style. Retreats, romantic weekends or adventurous getaways. Close to wineries, breweries, farmers market, and hiking. ★Sleep 16: K,K,K,Q,Qx2,bunkx2,sofa bed ★3,500sqft on 3 floors ★Hot tub ★Bluetooth sound system ★Vaulted ceiling, gas fireplace, 55” TV ★Movie room: 65” TV, pool table, wet bar, wine fridge ★Dining table for 10 ★Workspace ★Roku TV every bedroom ★Park 6 cars Seasonal outdoor pools/tennis access included.

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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, 170 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.

LocationFamilyBathroom

5.0 out of 5 average rating, 39 reviews

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'.

ValueLocationQuiet

4.99 out of 5 average rating, 110 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.

LocationFamilyDecor

5.0 out of 5 average rating, 242 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.

ValueFamilyWalkability

4.97 out of 5 average rating, 63 reviews

Luxury 4100+ sqft designer resort-style home in Wintergreen with top and unique amenities: • 6 bedrooms, 4.5 baths, 12 beds including 4 King beds • Game & media rooms: Pool table, shuffleboard, arcade machines, 100-inch TV, & home theater • Dining seating: Indoor (10-seat & 6-seat tables) + 3 bar stools • Outdoor spaces: 10-seat dining, 8-seat couch, fire pit, grill; 6-seat couch • Golf course-front with Mountain & Valley views • Backyard oasis: Hot tub, barrel sauna, cold plunge

LocationFamilyOutdoor spaces

A spacious deck is surrounded by greenery, featuring several black Adirondack chairs arranged around a firepit. The glass railing provides an unobstructed view of the outdoors, enhancing the inviting outdoor space.

4.99 out of 5 average rating, 173 reviews

151Escape | 5 Group Fun! Game Room/Bar/Deck/4kTVs

Enjoy mountain adventures with friends & family at this beautiful & newly renovated 5 bedroom mountain house ideally located in Virginia Wine Country at Wintergreen Resort’s Stoney Creek valley area. This amazing home features: - 75” & 55” 4k TVs - Fully equipped, live edge wet bar & bar countertop - Professional Ping Pong table - Deck with views, firepit & grill Just minutes from skiing, golf, hiking, wineries, breweries, apple-picking and other adventures the area offers all year long!

FamilyLocationQuiet

4.88 out of 5 average rating, 153 reviews

Home in Roseland

Blue Ridge Mt retreat steps off Appalachian Trail

Escape to this stunning 3-story Wintergreen mountain retreat, steps from the Blue Ridge Parkway and Appalachian Trail. Featuring a lighted circular driveway and three private porches, it offers ample space for relaxation. The top floor includes two bedrooms and a large bath. The main level boasts a den, kitchen, master bedroom, and a fully stocked kitchen with a 10-seat dining table. The bottom floor features another master bedroom and a bunk room. Unwind by the cozy fireplace or hot tub!

ValueLocationQuiet

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!

ValueFamilyIndoor spaces

4.97 out of 5 average rating, 130 reviews

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.

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Popular amenities for Wintergreen Resort house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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.

4.84 out of 5 average rating, 146 reviews

Walk to Ski! Hot Tub Pool Table EV Charger Dogs OK

FamilyLocationParking

A hot tub bubbles invitingly on a concrete pad in a spacious yard. Surrounding the tub is a well-maintained green lawn, with majestic mountains visible in the background. White Adirondack chairs are positioned nearby for relaxing moments outdoors.

5.0 out of 5 average rating, 113 reviews

Spacious retreat: Game Room, Hot Tub & Fire Pit

FamilyLocationCheckout

4.89 out of 5 average rating, 113 reviews

The bright living area features tall windows allowing natural light to illuminate the space. A fireplace creates a focal point, while comfortable seating is arranged around it. A staircase leads to the upper level, and outdoor views are visible through the glass doors.

Home in Roseland

Fall Retreat | King Beds | Hot Tub | Hiking

LocationFamilyGetting around

The open living area features high ceilings and large windows, allowing natural light to enhance the space. A comfortable seating arrangement includes a sofa and two armchairs, while an adjoining kitchen is visible in the background, equipped with modern appliances.

4.89 out of 5 average rating, 132 reviews

Mountain Bauhaus | Sleeps 8 | Amenities | Grill

LocationFamilyHospitality

4.94 out of 5 average rating, 163 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

LocationValueCleanliness

4.96 out of 5 average rating, 240 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

ValueLocationPool

4.92 out of 5 average rating, 49 reviews

Mid-Century Escape • Sleeps 10 • Breweries

FamilyLocationCleanliness

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.

4.99 out of 5 average rating, 67 reviews

Luxury Oasis |Ski, Hike, Winter fun| Pet friendly!

FamilyLocationParking

Weekly house rentals

4.97 out of 5 average rating, 30 reviews

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

LocationValueOutdoor spaces

A spacious living area is showcased, featuring a large kitchen island with dark cabinetry. Large windows invite natural light, revealing views of surrounding trees. Comfortable seating areas are arranged nearby, emphasizing an open-concept design that connects kitchen and lounge spaces.

5.0 out of 5 average rating, 59 reviews

Top of the Mountain Hideaway with Hot Tub!

LocationFamilyCondition

A spacious living area features large windows allowing natural light to flow in. Comfortable seating includes a dark leather sofa and a cozy armchair, surrounded by a round coffee table atop a soft rug. Art posters decorate the walls, and a television is positioned on a console beneath.

4.95 out of 5 average rating, 40 reviews

Luxe Cliff House Retreat: Hike, Sip, Relax

LocationFamilyNearby

5.0 out of 5 average rating, 22 reviews

Mountain View | Hot tub | Sleeps 14

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A spacious living area features a high vaulted ceiling with exposed wooden beams and a stone fireplace. Large windows allow natural light to fill the room, highlighting comfortable seating arrangements and decorative accents. A chandelier hangs above, complementing the rustic design.

4.93 out of 5 average rating, 30 reviews

Summit Serenity - Walk To Slopes and Restaurants

LocationValueCondition

An inviting living area features a large sectional couch and two patterned armchairs surrounding a modern coffee table. A mounted flat-screen TV is positioned above a stone fireplace, with large windows allowing natural light. A bar area with seating provides additional gathering space.

4.89 out of 5 average rating, 64 reviews

Renovated 4+BR luxury townhome @ the Mountain Top!

ValueFamilyIndoor spaces

5.0 out of 5 average rating, 52 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

LocationFamilyLayout

5.0 out of 5 average rating, 13 reviews

Blue Bear

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Private house rentals

5.0 out of 5 average rating, 16 reviews

Coziest Condo 1st floor, walk to the Patio Terrace

LocationFamilySleep quality

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.

4.88 out of 5 average rating, 33 reviews

Charming Wintergreen resort home

ValueLocationGetting around

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.

4.95 out of 5 average rating, 73 reviews

Panorama Peak Lodge-4 bedroom with sweeping views

LocationFamilySkiing

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, 52 reviews

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

LocationFamilyAmenities

A snow-covered slope is seen, with skiers and snowboarders enjoying the day. Trees line the edge of the hill, providing a natural border. In the background, multiple buildings are visible, reflecting a ski resort atmosphere under a clear blue sky.

4.93 out of 5 average rating, 46 reviews

Wintergreen Condo Ski In Ski Out

LocationValueLayout

A spacious mountain house is nestled among tall trees, surrounded by lush greenery. A gravel driveway leads to the entrance, showcasing the home's unique architectural features, including large windows that offer natural light.

5.0 out of 5 average rating, 21 reviews

Greyhaven II

FamilyLocationHospitality

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

LocationFamilyCleanliness

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.