Airbnb your place

House holiday rentals in Wintergreen

Find and book unique houses on Airbnb

Top-rated house rentals in Wintergreen

Guests agree: these houses are highly rated for location, cleanliness and more.

%{current} / %{total}1 / 1
Top guest favourite
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 trailsā€“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, 65ā€ 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 favourite
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 favourite
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

Top guest favourite
Home in Greenwood
5 out of 5 average rating, 221 reviews

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.

Top guest favourite
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 favourite
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. ā˜…Amazing mountain views ā˜…Hot tub for 6 people ā˜…Outdoor shower ā˜…Rockers, Adirondacks chairs for idle stargazing ā˜…Gas grill ā˜…Teak dining table seats 6 ā˜…Indoor/outdoor gas fireplaces ā˜…View 55ā€ TV from comfy leather sofa/kitchen ā˜…Pack 'n Play/Bassinet/High chair ā˜…Mud room

Top guest favourite
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 creekā€”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 favourite
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!

Guest favourite
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 favourite
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.

Guest favourite
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.
Home in Wintergreen Resort
4.8 out of 5 average rating, 132 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!

Superhost
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
4.89 out of 5 average rating, 109 reviews

Mountain Bauhaus | Sleeps 8 | Amenities | Grill

Welcome to your newly decorated and upgraded home in the Blue Ridge Mountains at Wintergreen Resort! A bright and welcoming feel will let you settle in and relax in no time. This space is perfect for families, groups, couples, and adventurous souls who want to explore the mountains or take in the beautiful mountain scenery. Please be sure the read below for Wintergreen Resort Amenities rules and accessibility during your stay.

Popular amenities for house rentals in Wintergreen

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Top guest favourite
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.

Top guest favourite
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!

Guest favourite
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 favourite
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 favourite
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 favourite
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 favourite
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 favourite
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

Weekly house rentals

Guest favourite
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 favourite
The modern cottage features a light-colored exterior with large windows and a red front door. A wooden deck extends from the entrance, surrounded by lush green grass and trees displaying autumn leaves in shades of orange and yellow.
Home in Afton
4.98 out of 5 average rating, 98 reviews

Cottage at Mountain View Meadow

Top guest favourite
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 favourite
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 favourite
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 favourite
A rustic black cottage is framed by blooming pink flowers and lush green grass. Large windows with white trim brighten the exterior. The surrounding landscape features gentle hills and seasonal greenery, creating a serene and inviting atmosphere.
Home in Afton
5 out of 5 average rating, 13 reviews

Aftonshire Cottage - Heart of Afton's Wine Region

Top guest favourite
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

Top guest favourite
Home in Afton
5 out of 5 average rating, 23 reviews

Rockwell Ridge: Dogwood Suite with Clawfoot Tub

Private house rentals

Top guest favourite
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.
Home in Wintergreen Resort
5 out of 5 average rating, 46 reviews

Luxury|Hot Tub|Sauna|Cold Plunge|Game Room|Views

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

The Treehouse at Wintergreen

Top guest favourite
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!

Top guest favourite
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
5 out of 5 average rating, 47 reviews

Wintergreen Mountain Retreat

Guest favourite
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

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 favourite
A spacious deck features two lounge chairs and two wooden rocking chairs, offering a setting for relaxation. The surrounding area showcases lush green mountains under a clear blue sky, with expansive views of the valley below.
Home in Afton
4.97 out of 5 average rating, 59 reviews

Mountain Homestead - Hottub, King, Dogs, Gameroom

Destinations to explore

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