Whole House Rentals & Vacation Homes

1566 Vistas Condo is a renovated top-floor, three-bedroom, three-bath condo with skylights, ridgeline views, and quick access to Wintergreen spa and Devil's Knob. 1566 Vistas Condo crowns its building with skylights, ridgeline panoramas, and three ensuite bedrooms, steps from the spa and Devil's Knob facilities.

779 Blue Ridge Drive is a four-bedroom, 4.5-bath mountain home with hot tub, gas fireplace, and king beds in every suite, located four minutes from skiing. Four king suites, a bubbling hot tub, and a great room anchored by a stone fireplace make 779 Blue Ridge Drive a go-to for families who want to be on the slopes in under five minutes.

Adventure Awaits is a pet-friendly Wintergreen home two minutes from the slopes with hot tub, fire pit, multiple living areas, and five smart TVs. Adventure Awaits lives up to its name with a hot tub, multiple lounges, pet-friendly policies, and a location two minutes from Wintergreen's slopes and hiking shuttles.

Altitude Adjustment is a five-bedroom, four-bath mountain retreat with large windows, multiple decks, high-flame fire pit, sauna, outdoor shower, game room, and EV charger. The whole group will love this spacious and unique space.

Arrowwood Lane is a four-bedroom Wintergreen home sleeping 10 with covered hot tub, dual living areas with fireplaces, deck, and central HVAC. There are two separate living areas, each with a fire place.

Art & Soul Guesthouse is a design-forward one-bedroom plus loft retreat with sauna, EV charger, and sunset views, steps from Nelson 151 adventures.

Art & Soul Main House offers three en-suite bedrooms plus loft sleeping, gourmet kitchen, saltwater hot tub, dry sauna, and extensive decks for groups up to ten. And stunning landscapes and skies.

Avon Hill is a 100-acre Rockfish River estate with multiple lodging buildings, boxwood gardens, pool, and Bruce's Barn event venue for weddings and retreats. For 150 and makes the perfect setting for your destination wedding.

Updated, well appointed and received consistent fiive star ratings.

Blue Ridge Mountain Retreat is a 4,800-square-foot Wintergreen luxury home sleeping 20 with four wood-burning fireplaces, gourmet kitchen, and game room. This home is an amazing 4800 square foot luxury home located just a short distance from Mountain Inn, ski areas, Founders Vision Overlook, Devil’s Knob Golf Course, Tennis Center, Spa, and Fitness Center.

Blue Sky Retreat is a luxury 4,100+ sq ft designer home with six bedrooms, media and game rooms, sauna, cold plunge, hot tub, and golf course frontage with mountain views. Blue Sky Retreat spans 4,100 designer square feet with six bedrooms, media and game rooms, sauna, cold plunge, and golf-course frontage that frames the Blue Ridge.

Boho Cliff House Retreat offers dramatic Blue Ridge views in a design-forward setting—ideal for couples or friends seeking a stylish mountain escape.

The Branch at Afton Mountain Retreat is a remodeled three-bedroom home with screened porch fireplace, pet-friendly policy for hypoallergenic dogs, and location across from Veritas.

The Bungalow at Afton Mountain Retreat is a renovated 1930s Sears Roebuck home with open concept living, marble bath, kid playroom, and mountain views over Veritas.

Chateau Greenstone is a six-bedroom, four-bath Wintergreen retreat sleeping 18 with multiple game zones, 'zen den,' heated TV porch, hot tub, sauna, and four outdoor gathering areas. We wanted to design a getaway that truly has something for everyone and we think Chateau Greenstone gets as close to this lofty goal as any Wintergreen Property.

Cliffs Edge is a Southern Living-featured contemporary mountain home with floor-to-ceiling windows, cantilevered decks, shoji screens, and dramatic Crawford's Knob views. An open floor plan with high ceilings and large skylights, this amazingly engineered home will stun you with its incredible mountain views.

Cuatro Climas at 130 Pedlars Point is a four-bedroom, 3.5-bath Wintergreen house five minutes from resort amenities, with wood-burning fireplace, mountain views, and multiple levels. Cuatro Climas spans multiple levels with a wood-burning hearth, mountain vistas, and four bedrooms just five minutes from Wintergreen's core amenities.

D & D's Mountain Home is a renovated two-bedroom Stone Ridge condo with gas fireplace, patio, and views over Devils Knob Golf Course.

Dobie Condo 323 is a two-bedroom, two-bath Wintergreen condo with fireplace and immediate access to resort entertainment for ski weekends or quiet retreats. The resort is found on the Sunrise Side of the Blue Ridge Mountains and is conveniently located close to Charlottesville, Staunton, Lynchburg, and Waynesboro.

Elk Mountain Overlook is a boutique chalet perched off the Blue Ridge Parkway with two king suites, soaker tub, dual-head shower, and expansive deck views. Mountaintop overlook with jaw dropping views and camp themed interior design.

Ethan's Den is a stylish one-bedroom suite with live-edge breakfast bar, heated floors, fireplace, and luxe finishes for couples getaways. Ethan's Den has been decorated to compliment the beautiful setting it is in.

Step into a beautifully crafted retreat where a stunning live-edge oak breakfast bar with leather stools awaits. This inviting space is perfect for enjoying your morning coffee or gathering with friends and family.<br><br>Experience the charm and comfort of this exceptional home, designed to provide a memorable stay.

Four Elements Farm is a 116-acre retreat with farmhouse lodging, hot tub, pond, friendly goats, and proximity to Devils Backbone and Wintergreen. Four Elements Farm stretches across 116 acres of pasture, pond, and woodland, offering farmhouse lodging, a hot tub, and friendly resident goats between Devils Backbone and Wintergreen.

Grace's Place Petite Retreats offers four well-appointed tiny homes exclusively for registered guests, each with curated amenities for a boutique stay. We offer 4 well appointed tiny homes listed on Airbnb.

Fifteen-acre Heart Rock homestead with lodging for up to 15, edible gardens, and retreat spaces minutes from breweries and river access. Located in Nelson County, Virginia, our fifteen acre homestead offers both rustic charm and modern comfort. Nelson County has something for everyone..

Highlands 1426 Condo is a renovated two-bedroom, two-bath ski-front condo with sunrise vistas, easy entry, and property manager nearby for Wintergreen stays. Highlands 1426 condenses sunrise views, ski-front access, and fresh renovations into a two-bedroom condo, backed by a nearby property manager for worry-free Wintergreen stays.

Home on the Ridge is a two-bedroom, two-bath condo overlooking the 18th hole at Devils Knob with kitchen, balcony, and easy access to golf, tennis, and skiing. Home on the Ridge overlooks Devils Knob's 18th hole, giving condo guests a balcony for post-round drinks, full kitchen for easy meals, and immediate access to golf, tennis, and skiing.

Love of Mountains Oh Fill My Cup is a modern third-floor two-bedroom condo with upgraded kitchen, private golf course views, and access to public/community pools at Wintergreen. Relax with the whole family at this peaceful place to stay.

Marigold on the Mountain is a five-bedroom, four-bath Wintergreen home sleeping 14 with hot tub, cedar barrel sauna, two-tier deck with fire pit, and separate game room. Marigold on the Mountain was built for big groups—five bedrooms, four baths, a hot tub, cedar barrel sauna, two-tier deck with fire pit, and a separate game room handle up to 14 guests in style.

Meili Mountain offers rustic creekside camping on private land for quiet, leave-no-trace stays near Nelson County trails.

Mima's Mountain House is a five-bedroom, three-bath creekside retreat sleeping ten with porch views of The Priest and easy access to Route 56 adventures.

Mountain & Vine Farmhouse is a 2,700-square-foot retreat overlooking Delfosse Vineyards with deck, gas grill, and four queen bedrooms for wine country gatherings. 5-bath vacation rental home overlooking Delfosse Vineyards and Winery 2,700 Sq Ft | Deck | Gas Grill | Free Wi Fi Relax, reset, and rejuvenate in this stunning Faber farmhouse - perfect for a peaceful weekend getaway with your best friends.

Mountain Dacha is a four-bedroom, three-bath home adjacent to a Wintergreen golf course with cozy interiors suited for year-round resort activities.

Mountain Dreams Condo at The Ledges offers two-story living with two bedrooms, dual fireplaces, redesigned king suite, and expansive views over the Rockfish Valley. A brand new Dream Cloud King size bed is in the lower suite with a queen and bunks in the guest room.

Mountain View Vista is a one-bedroom, two-bath Wintergreen condo with spacious kitchen, large deck, and sweeping mountain vistas for couples getaways. 1 Bedroom/2 full baths/ large kitchen Large deck with scenic views.

Nectar Landing is a three-bedroom, 2.5-bath ranch sleeping ten with game room, Wi-Fi, front porch, back deck hot tub, and open-concept kitchen perfect for multi-family trips. Nectar Landing mixes indoor-outdoor fun via a game room, open kitchen, front porch rockers, and a back-deck hot tub, sleeping up to ten guests in a single-level layout.

Nelson 151 Views and Brews is a one-bedroom apartment with full kitchen and washer/dryer, offering Humpback Rock views and proximity to the Route 151 craft beverage trail.

Nine Ridges Retreat is a six-guest mountain home on 20 acres with artisan furnishings, sweeping Three Ridges views, and close access to Crabtree Falls and the Parkway.

Our Mountain Getaway is a six-bedroom, 5.5-bath Wintergreen home overlooking the 12th hole with expansive views, ideal for large groups. Our Mountain Getaway overlooks the 12th hole and packs six bedrooms plus 5.5 baths, giving large families plenty of elbow room and panoramic valley views.

Panoramic Peak is a renovated one-bedroom, two-bath Wintergreen condo with sweeping valley views, sleeper sofa, and summer access to resort pools.

Peaceful Mountain Getaway is a pet-friendly Wintergreen retreat with calming décor and hosts available to assist, perfect for families seeking quiet escapes. One story, three bedroom, two bath, well stocked house in Rodes Valley.

Peaktime is a one-bedroom apartment with kitchenette, ideal for couples seeking a simple base near Nelson 151 and Wintergreen.

Red, White and Wintergreen is a five-bedroom Wintergreen property with large deck, porch hot tub, valley views, and office space for remote-friendly stays. It is perfect for families and large groups with comfortable living areas and a great deck and porch with hot tub.

Remodeled 3BR/2BA Ski Chalet off Tyro Slope offers ski-in/out access, gourmet kitchen, heated bathroom floors, wraparound deck, and parking for three. This quaint remodeled Austrian styled 3BR/2BA ski chalet just one row off the Tyro Slopes.

The Retreat at Three Ridges is a Scandinavian-inspired Wintergreen condo just a three-minute walk from the slopes, featuring a modern aesthetic, cozy fireplace with provided wood, well-stocked kitchen, and relaxing outdoor space. Scandi style meets mountain coziness at The Retreat at Three Ridges, where wood-burning fires, a sleek kitchen, and a quick three-minute stroll deliver you to Wintergreen's lifts.

Rockfish Tiny Home is a modern tiny retreat with hot tub, fire pit, hanging swing, and spacious interior central to Nelson 151 wineries. Nelson County has something for everyone.

Rockfish Valley Retreat is a three-bedroom, two-bath valley home sleeping nine with outdoor space, horse farm views, and short drives to trails, wineries, and breweries. Rockfish Valley Retreat frames horse farm vistas from its decks, sleeps nine guests, and keeps wineries, breweries, and trailheads just a short country drive away.

Inside, the open kitchen and multiple sleep spaces comfortably host up to ten guests for winery weekends or fishing-focused family reunions. Escape to this spacious retreat with a hot tub and everything else you need to get away.

Serenity Summit is a three-bedroom, 3.5-bath Wintergreen home sleeping eight with modern amenities, family-friendly layout, and serene wooded surroundings.

Ski in Style at Sapphire Squirrel is a three-bedroom Wintergreen home steps from the slopes with fully equipped kitchen, dedicated workspace, deck, and gas grill for up to six guests.

Skis and Trees is a ski-in/ski-out Tyro slope chalet with two king master suites, kids loft, six-person hot tub, and renovated gourmet kitchen. Completely renovated, 3 BR/2BA chalet, located on Lower Tyro slope, just below Tequila.

Sleepy Hollow is nestled in scenic rural Nelson County, Virginia.

Slopes at Tyro is a slope-side four-bedroom Wintergreen home with hot tub and wood-burning fireplace providing direct ski-in/ski-out access, including night skiing. Our property manager at Wintergreen is Julie Fitzgerald.

Straw Bale House is an eco-friendly custom home on 70 acres near breweries with farm animals, fresh eggs, and private hiking. The hand-built Straw Bale House stays cool in summer and cozy in winter, thanks to its eco-friendly construction on 70 acres of fields and woods.

Sunset Vista Villa is a two-bedroom, two-bath Wintergreen condo with elevated first-floor views, ideal for sunset watching and family getaways. Welcome to Sunset Vista Villa, this stunning 2 bedroom, 2 bathroom retreat offers breathtaking views that stretch for miles.

The Treehouse is a 3,200 sq ft modern home on ten acres with hot tub, outdoor shower, 10-person dining, fire pit, heated floors, and award-winning design minutes from breweries and Charlottesville. The Treehouse spreads across ten wooded acres, pairing award-winning architecture with heated floors, expansive dining space, hot tub, outdoor shower, and easy drives to Charlottesville breweries.

Time Out is a pet-friendly Wintergreen escape sleeping seven with hot tub, fast Wi-Fi, smart TVs, and three queen bedrooms plus single sofa bed. Activities are endless: apple picking, breweries/wineries, hiking, lake, horseback riding, golf, tennis, skiiing.

Time to Wine Down is a five-bedroom Afton retreat on two acres with dual living rooms, basement game space, air hockey, expansive fire pit, and string-lit outdoor dining near the Route 151 beverage trail. What makes Time to Wine Down truly unique is its perfect blend of vintage charm and modern amenities, all set on two peaceful acres in the heart of Virginia's wine country.

Top of The Mountain Hideaway is a three-bedroom, three-bath Wintergreen home near the Mountain Inn featuring hot tub, shuffleboard table, and easy access to wineries and breweries. Top of The Mountain Hideaway places you near the Mountain Inn yet still feels private, thanks to a hot tub deck, shuffleboard lounge, and three bedrooms with en-suite baths.

The View at Crawfords Edge is a four-bedroom, four-ensuite Wintergreen retreat with multi-level outdoor living, fire table, pizza oven, vaulted ceilings, and dual living rooms. The View at Crawfords Edge layers four ensuite bedrooms, vaulted living spaces, a pizza oven, and tiered outdoor lounges so your group can toast sunsets high above Wintergreen.

Wake in the Clouds is a renovated one-bedroom, two-bath condo with spectacular sunrises, modern finishes, and resort convenience. Wake in the Clouds is aptly named—this renovated one-bedroom, two-bath condo faces the sunrise, offering modern finishes and instant access to Wintergreen amenities.

Wintergreen Condo 1437 Highlands is a ski-in/ski-out Highlands building condo showcasing incredible views and modern finishes steps from resort amenities. Highlands 1437 offers true ski-in/ski-out access plus sweeping valley vistas, making the refreshed condo a smart pick for guests who want modern finishes right above the slopes.

Wintergreen Duplex is a three-floor, four-bedroom, 3.5-bath townhome with wood-burning fireplace, back deck, laundry, and shuttle access across from the spa. Across from the Wintergreen Spa, Wintergreen Duplex stacks three floors, four bedrooms, and 3.5 baths into a townhome with a wood-burning hearth, back deck, laundry, and front-door shuttle access.

Wintergreen Getaway for Families is a pet-friendly mountain home with two outdoor seating areas, indoor fireplace, and pool/tennis access located minutes from Wintergreen slopes. The resort is found on the Sunrise Side of the Blue Ridge Mountains and is conveniently located close to Charlottesville, Staunton, Lynchburg, and Waynesboro.

Wintergreen Ridge Retreat is a four-bedroom mountain home sleeping ten with expansive decks, hot tub, and easy access to Wintergreen lifts and trails. Wintergreen Ridge Retreat sleeps ten across four bedrooms, surrounding guests with wraparound decks, a bubbling hot tub, and instant access to resort lifts and trailheads.

Wintergreen Vistas comprises two ridge-line condos—one two-bedroom, one three-bedroom—each with full kitchens, decks, and standout Blue Ridge views. One is a 2 bedroom, 2 bath unit, while the other is 3 bedroom, 3 bath The resort is found on the Sunrise Side of the Blue Ridge Mountains and is conveniently located close to Charlottesville, Staunton, Lynchburg, and Waynesboro.

Winterhaven is a five-bedroom, 4.5-bath Wintergreen house half a mile from the lodge with updated interiors for large groups.

Woodland Hideaway is a one-bedroom apartment with separate entrance, full kitchen, dining area, and access to forest trails and Dutch Creek on a secluded property. Woodland Hideaway gives guests their own private apartment—full kitchen, dining nook, and forest-trail access to Dutch Creek—tucked within a larger wooded property.

Woodson's Mill House is a craftsman retreat beside historic Woodson's Mill with lake access, wooded acreage, and convenient access to Charlottesville and Wintergreen. Woodson's Mill House backs up to the historic gristmill and a spring-fed lake, creating a storybook backdrop for a craftsman-style retreat.