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.

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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.

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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, 168 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.

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5.0 out of 5 average rating, 38 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'.

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4.97 out of 5 average rating, 62 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

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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!

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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!

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4.97 out of 5 average rating, 130 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.

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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, 139 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!

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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.

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4.94 out of 5 average rating, 102 reviews

Pickleball | 2 Homes | Sleeps 19 | 151 Brew Trail

Nelly's Retreat is located in the lovely rolling hills of Nellysford, VA. The property includes 2 spacious homes that sleep up to 19 guests. Our unique property is perfect for bachelor/bachelorette groups, reunions, business retreats, and multi family getaways. Nelly's Retreat is centrally located to over a dozen wedding venues and is just off the Route 151 Wine/Brew Trail. We are minutes away from Shenandoah National Park and Wintergreen Resort!

LocationFamilyOutdoor spaces

A spacious living area features vaulted ceilings, large windows that invite natural light, and a stone fireplace as a focal point. Comfortable seating includes two armchairs and a dark sofa adorned with decorative pillows. A dining table is visible with a backdrop of green trees.

4.99 out of 5 average rating, 113 reviews

Relax Among the Trees at the Canopy House

Escape to The Canopy House, a spacious light-filled 4 bedroom retreat at Wintergreen Resort, just 5 minutes from the slopes and walkable to scenic trails. Perfect for families and groups, enjoy 2 king ensuites, a queen bedroom, bunk room, stocked kitchen, fireplace, playroom, and screened porch with fire table. Ski, hike or explore Route 151 wineries and breweries, then relax among the trees. Sleeps 8 with an EV charger available.

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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

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, 172 reviews

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

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A spacious open living area features large windows offering natural light and views of the outdoors. The area includes a comfortable sofa, dining space with chairs, and a modern kitchen equipped with a stylish island and fixtures, enhancing the room's contemporary rustic feel.

4.83 out of 5 average rating, 142 reviews

Designer Home: A+ Views HotTub Pool GameRoom Grill

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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.

4.83 out of 5 average rating, 144 reviews

Hot Tub EV Charger Pool Table Dogs OK Tennis Golf

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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, 112 reviews

Spacious retreat: Game Room, Hot Tub & Fire Pit

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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, 130 reviews

Mountain Bauhaus | Sleeps 8 | Amenities | Grill

ValueFamilyOutdoor spaces

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

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4.94 out of 5 average rating, 162 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

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4.96 out of 5 average rating, 239 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

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Weekly house rentals

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, 58 reviews

Top of the Mountain Hideaway with Hot Tub!

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An expansive deck is illuminated by string lights, featuring a central firepit surrounded by four wooden chairs. In the background, a warm glow reflects off a salt-water hot tub, creating a cozy outdoor atmosphere.

5.0 out of 5 average rating, 54 reviews

Escape the Heat•10° Cooler•Hot Tub•Fire Pit•4BR/BA

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4.97 out of 5 average rating, 29 reviews

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

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4.98 out of 5 average rating, 46 reviews

Wintergreen 5BR | Hot Tub | Sauna | Firepit

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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!

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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

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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!

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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, 45 reviews

Wintergreen Condo Ski In Ski Out

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Private house rentals

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, 61 reviews

Luxury House on Mountain Golf Course near Slopes

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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, 86 reviews

Heart of Wintergreen, Hot Tub, Fireplace

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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

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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.

4.98 out of 5 average rating, 45 reviews

Premiere 2 BR Getaway Ski In/Out Wintergreen Condo

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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, 37 reviews

Luxe Cliff House Retreat: Hike, Sip, Relax

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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

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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.

4.99 out of 5 average rating, 68 reviews

Stunning Views, Hot Tub, Impeccable Design

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A picnic table is positioned on a grassy area, offering expansive views of rolling mountains under a partly cloudy sky. Lush greenery surrounds the table, creating a serene outdoor setting for relaxation or enjoying a meal.