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.

LocationValueComfort

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 spacious great room features large windows, allowing natural light to fill the space while offering views of the surrounding trees. A comfortable sofa is positioned in front of a large television, and a dining table for eight is set nearby. Decorative accents include a chandelier and cozy armchairs.

4.95 out of 5 average rating, 110 reviews

Mntn View Pool Table Dogs OK Pool Tennis Golf Hike

7min WALK or 4min drive to slopes! Mountain estate amidst an aboral oasis with spectacular mountain views. Work remotely w/ FAST Wi-Fi. Close to wineries, breweries, farmers markets, hiking and Upper Shamokin Falls trail. ★3,160sqft of living ★Comfortably Sleep 10: K, K, K + bunk, D, sofa bed ★Dining table for 8 ★Great room w/ fireplace ★Incredible mountain view ★Pool table ★Movie room ★Dog and family-friendly Happy pet fee $187. Outdoor pool/tennis access included. Resort access not included.

LocationFamilyPets

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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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

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.

FamilyValueGetting around

4.99 out of 5 average rating, 172 reviews

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.

Home in Nellysford

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!

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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!

ValueFamilyOutdoor spaces

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.

FamilyLocationHospitality

4.94 out of 5 average rating, 105 reviews

Designer Home w/ Incredible Views, Sleeps 16

Welcome to Highlands Overlook, a designer-decorated home in the heart of Wintergreen. The deck is second-to-none, complete with hot tub, cedar barrel sauna, fire table, dining for 10, grill, smoker, pizza oven, and views everywhere. The light-drenched interior is equally impressive. With 6 bedrooms plus a private game room with pullout sofa, the home sleeps 16 comfortably. Plus, pet friendly! Managed by Chris at New School Hosting- click on his profile below to see more reviews.

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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!

ValueFamilyWi-Fi

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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Popular amenities for Wintergreen Resort house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.89 out of 5 average rating, 130 reviews

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.

Home in Nellysford

Mountain Bauhaus | Sleeps 8 | Amenities | Grill

FamilyValueAccuracy

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

ValueLocationCondition

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

FamilyLocationLaundry

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

LocationValueShared spaces

4.97 out of 5 average rating, 62 reviews

LocationFamilyAmenities

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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4.92 out of 5 average rating, 48 reviews

Mid-Century Escape • Sleeps 12 • Breweries

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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 | Hike, Lakes, Golf | Pet friendly!

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Weekly house rentals

5.0 out of 5 average rating, 38 reviews

Best Blue Ridge Views at Sunrise over Wintergreen

ValueLocationDecor

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!

ValueFamilyKitchen

5.0 out of 5 average rating, 21 reviews

Mountain View | Hot tub | Sleeps 14

FamilyLocationBackyard

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

FamilyLocationAccess

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

LocationValueHiking

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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A circular firepit is surrounded by four wooden Adirondack chairs, arranged thoughtfully on a gravel surface. Natural light filters through nearby trees, creating a serene outdoor seating area, perfect for gatherings or quiet reflections.

5.0 out of 5 average rating, 13 reviews

Blue Bear

LocationFamilyIndoor spaces

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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Private house rentals

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

LocationValueCleanliness

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

ValueFamilyCheck-in

A stone patio area is set against a backdrop of lush greenery, featuring a rectangular table and two matching benches. Flagstone pathways lead to the seating area, while surrounding garden elements enhance the outdoor space. The area offers an unobstructed view of the hillside.

5.0 out of 5 average rating, 16 reviews

Ski-in ski out!

LocationFamilySleep quality

5.0 out of 5 average rating, 37 reviews

White Wolf Chalet at Wintergreen

FamilyLocationQuiet

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

ValueLocationCleanliness

4.88 out of 5 average rating, 33 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

LocationFamilyLayout

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, 65 reviews

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

ValueLocationCheckout

The exterior of the cabin is presented, showcasing a two-story structure surrounded by trees. A welcoming porch with two chairs is visible at the entrance, and wide steps lead up to the front door. Natural light highlights the exterior's neutral tones.