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House vacation rentals in Wintergreen

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Top-rated house rentals in Wintergreen

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Top guest favorite
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.
Home in Wintergreen Resort
4.99 out of 5 average rating, 149 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.

Top guest favorite
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.
Home in Wintergreen Resort
4.97 out of 5 average rating, 215 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.

Guest favorite
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.
Home in Wintergreen Resort
4.96 out of 5 average rating, 119 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

Guest favorite
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.
Home in Wintergreen Resort
4.94 out of 5 average rating, 140 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.

Top guest favorite
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
4.99 out of 5 average rating, 148 reviews

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

Top guest favorite
A brand new farmhouse is showcased in a snowy landscape, featuring a welcoming wooden door framed by large windows. The front porch includes rocking chairs, while a fenced area and mountains provide a scenic backdrop.
Home in Roseland
4.97 out of 5 average rating, 106 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

Top guest favorite
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
4.99 out of 5 average rating, 283 reviews

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.

Top guest favorite
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
4.99 out of 5 average rating, 158 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!

Top guest favorite
Home in North Garden
4.97 out of 5 average rating, 371 reviews

Lux Country Retreat minutes from Charlottesville!

Located just off route 29 this private luxury retreat with surrounding 2 acre fenced yard is one mile from Pippin Hill Farm & Vineyard and only 15 minutes from UVA/Charlottesville. You will find this home spacious, bright and airy, perfect for entertaining groups or families. The house is completely equipped with everything you may need to host the perfect getaway! Nearby attractions: Pippin Hill, Albemarle Ciderworks, Ragged Branch Distillery, Potter's Craft Cider and Charlottesville!

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.
Home in Wintergreen Resort
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.

Guest favorite
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.
Home in Wintergreen Resort
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!

Top guest favorite
Home in Wintergreen Resort
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 house rentals

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Top guest favorite
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.
Home in Wintergreen Resort
4.96 out of 5 average rating, 111 reviews

Cozy 5-bedroom home for large gatherings.

Guest favorite
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
4.93 out of 5 average rating, 233 reviews

Pine Lake Lodge

Guest favorite
The exterior of a multi-level home is nestled among trees, with warm lighting illuminating the porch and deck. The spacious deck features a staircase leading down, surrounded by autumn leaves, creating a welcoming atmosphere.
Home in Wintergreen Resort
4.89 out of 5 average rating, 150 reviews

Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat

Top guest favorite
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
4.96 out of 5 average rating, 229 reviews

Seasonal Private Pool - All Year Hot Tub

Guest favorite
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.
Home in Wintergreen Resort
4.91 out of 5 average rating, 46 reviews

Forest Cabin Getaway: Hike, Soak, Play

Guest favorite
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
4.94 out of 5 average rating, 154 reviews

Farmhouse on Working Vineyard

Top guest favorite
Home in Crozet
5 out of 5 average rating, 7 reviews

Hot Tub and Pool Mountain Views Wine Country

Guest favorite
The spacious living room features large windows that frame expansive mountain views. A comfortable sectional sofa and armchairs surround a wooden coffee table. The room is illuminated by natural light, with a stylish chandelier adding elegance. A dining area for six is visible in the background.
Home in Wintergreen Resort
4.93 out of 5 average rating, 85 reviews

Designer Home w/ Incredible Views, Sleeps 16

Weekly house rentals

Guest favorite
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.
Home in Wintergreen Resort
4.93 out of 5 average rating, 40 reviews

Wren Time

Top guest favorite
A cozy living area features a light-colored sofa facing a fireplace, creating a focal point. To the side, a comfortable armchair is paired with a small side table. A television is positioned across the room, with natural light illuminating the space from large, partly draped windows.
Home in Staunton
4.99 out of 5 average rating, 70 reviews

The Red Hen Historic Cottage

Top guest favorite
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.
Home in Roseland
4.99 out of 5 average rating, 72 reviews

Cozy Farmhouse W/Mountain Views

Top guest favorite
Home in Roseland
4.94 out of 5 average rating, 81 reviews

The Treehouse at Wintergreen

Top guest favorite
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.
Home in Wintergreen Resort
5 out of 5 average rating, 17 reviews

Away from it ALL

Top guest favorite
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.
Home in Wintergreen Resort
5 out of 5 average rating, 31 reviews

White Wolf Chalet at Wintergreen

Guest favorite
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
4.87 out of 5 average rating, 39 reviews

Mountain retreat with hot tub

Top guest favorite
A contemporary home is showcased against a wooded backdrop, featuring large windows that enhance natural light. A spacious deck is fitted with seating and a dining table, inviting outdoor relaxation. Decorative string lights add a subtle charm, highlighting the entrance area.
Home in Nellysford
4.97 out of 5 average rating, 59 reviews

Glass & Pine, close to Bold Rock & Vineyards

Private house rentals

Top guest favorite
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.
Home in Wintergreen Resort
4.98 out of 5 average rating, 49 reviews

Stunning Views, Hot Tub, Impeccable Design

Top guest favorite
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
4.95 out of 5 average rating, 41 reviews

Hot Tub! Wintergreen Resort!

Top guest favorite
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.
Home in Wintergreen Resort
4.96 out of 5 average rating, 49 reviews

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

Top guest favorite
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.
Home in Wintergreen Resort
4.94 out of 5 average rating, 67 reviews

Wintergreen Condo~ 1 Minute To Four Seasons Resort

Top guest favorite
An inviting outdoor space features a hot tub, a gas fire pit, and comfortable seating arrangements. The area is designed for relaxation, showcasing smooth wooden decking and views of the surrounding trees. Sliding glass doors provide access to the interior of the home.
Home in Wintergreen Resort
5 out of 5 average rating, 72 reviews

Luxe Modern Retreat: Steps to Ski & Hike! Views!

Superhost
The lodge exterior features a unique stone facade, complemented by large floor-to-ceiling windows that invite natural light. A spacious deck extends from the building, surrounded by tall trees and a natural landscape, providing a serene and inviting atmosphere.
Home in Wintergreen Resort
5 out of 5 average rating, 3 reviews

NEW! Ski-In/Ski-Out Retreat | Hot Tub + Fire Pit

Top guest favorite
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.
Home in Wintergreen Resort
4.94 out of 5 average rating, 69 reviews

Panorama Peak Lodge-4 bedroom with sweeping views

Guest favorite
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.
Home in Wintergreen Resort
5 out of 5 average rating, 9 reviews

The SnowHouse HotTub Dogs OK Firepit Creek PacMan

Destinations to explore

  1. Airbnb
  2. United States
  3. Virginia
  4. Nelson County
  5. Wintergreen
  6. House rentals