Family-friendly vacation 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.

Indoor spacesFamilyOutdoor spaces

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, 176 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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Vacation home in Lovingston

The cabin's exterior is surrounded by lush greenery, featuring a spacious porch with seating and a hot tub nearby. The two-story structure is constructed of wood, with large windows allowing natural light to fill the interior. A picnic table is located in the yard.

4.96 out of 5 average rating, 271 reviews

Ultimate cabin in the mountains

This unique and secluded cabin sits on 75 acres in the Blue Ridge mountains. Enjoy the cozy wood fireplace, hot tub, charcoal grill, and fast, reliable fiberoptic internet if you need to get some work done while you're away. It has a washer and dryer, a full kitchen, and is pet-friendly (no pet fee!), so you can enjoy it with the whole family. There is a 4K 55” smart TV with apps, a Tesla LVL 2 charger, a cabinet full of board games, books, and plenty of items to entertain both kids and adults!

KitchenIndoor spacesWifi

Villa in Wintergreen Resort

A spacious living area is highlighted by large floor-to-ceiling windows, offering views of the surrounding trees. A comfortable gray sofa and a round glass coffee table are present, along with a wooden dining table that seats six. An electric fireplace adds warmth to the space.

4.96 out of 5 average rating, 146 reviews

NO STEP ENTRY Wintergreen Mtn Home,HotTub,Sleeps10

We had to create a new listing for this property. Previous listing had 70+ reviews with a 4.8 Star rating. Same great host and same great house, just a new listing. Screenshots of old listing in additional photos. Stay at this luxurious 4-bedroom, 3-full bath vacation rental home for 10 in Wintergreen, within minutes of top-notch golf courses, skiing / snow boarding at the Mountain Inn, and dozens of hiking trails . In addition to the unbeatable location, the property offers a private hot tub!

KitchenFamilySkiing

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, 166 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.

KitchenIndoor spacesDecor

The living area features large sliding glass doors that open to a stunning view of the mountains. A modern dining table is positioned nearby, illuminated by a pendant light. Comfortable seating is arranged around the room, enhancing the inviting atmosphere.

4.98 out of 5 average rating, 131 reviews

Luxury Condo in the Sky! Finest in Wintergreen!

Welcome to our recently renovated luxury condo in the sky! Perched on the edge of the Wintergreen ridgeline, we are just a stone’s throw from nature’s bounty. Our condo offers the perfect blend of relaxation and access to recreation. Hit the ski slopes, take a hike, or explore the bountiful brew and wine scene and then come enjoy the view. The horizon is 75 miles distant from our balcony on a clear day! We love hosting families with kids or couples coming to enjoy all that Wintergreen offers!

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Apartment in Wintergreen Resort

The living area features a comfortable sectional sofa and a wooden coffee table, with a visible fireplace centrally located. Large windows provide natural light and views of the outdoor space. A mounted television is positioned above the fireplace, complementing the cozy ambiance.

4.85 out of 5 average rating, 107 reviews

Wintergreen Getaway

Relax with the whole family at this peaceful place to stay. Enjoy morning coffee and evening cocktails on the deck fronting the golf course. You will love the location and features! Walking distance to spa, The Wintergreen Nature Foundation, and Fire & Frost. Convenient to slopes, Chestnut Springs pool and Upper Shamokin Falls. A great place to relax after a full day of hitting nearby slopes or hiking trails, and exploring Nelson 151's winery and brewery attractions. Stairs to access. WiFi!

Indoor spacesFamilyNearby

Superhost

A private furnished patio features a cozy seating area with light-colored cushions on a dark frame sofa. A wooden coffee table sits in front, accented by a woven rug. The surrounding greenery adds a natural backdrop, creating a peaceful setting for relaxation.

4.92 out of 5 average rating, 213 reviews

1 bedroom condo, close to hikes & breweries & pool

Cozy 1BR Wintergreen condo 🌳 🌄 Close to scenic hikes, local breweries and wineries. The resort village, and mountain-top market, just minutes away. Enjoy a fully stocked kitchen, premium coffee and teas, cooking oils and spices. Relax after a day outdoors and enjoy a smart TV, fast WiFi and games. Comfortable queen bed in the bedroom plus new queen sleeper sofa in the living room. Private furnished patio with peaceful wooded views and or cool off in the heated community pool.

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4.97 out of 5 average rating, 127 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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4.99 out of 5 average rating, 374 reviews

Cabin in Vesuvius

The Sanctuary

Nature lovers paradise! Named "The Sanctuary" for the place you can UNPLUG, unwind & find your peace! Perched up high on nearly 60 acres- you are sure to get fresh air & the rest you are searching for! Only 4 miles to Wintergreen, 6 miles to Sherando lake and backs up to the Blue Ridge Parkway there are plenty of things to do OR just relax and enjoy the crickets & stars! With crazy careers, growing kids & constant hustle- everyone needs a hide out like this every now and then!

FamilyKitchenDecor

A cozy living area features a teal sofa with a yellow accent pillow and a light wood coffee table. The kitchen is adjacent, showcasing modern appliances. Stairs lead to the loft bedroom. Artwork hangs on the wall, and natural light enters through high windows.

4.95 out of 5 average rating, 177 reviews

Ski-In Ski-Out ~ Mtn Views ~ King Suite

Just steps from Wintergreen Resort’s slopes, Slope Side Gem offers the perfect mountain escape! Located in the heart of Mountain Village next to the Mountain Inn, you’re just a short walk to Starbucks, The Market, shops, and three restaurants and bars. Whether you’re skiing, hiking, golfing, or enjoying a local brewery or winery, adventure is at your doorstep. After an exciting day, unwind on the private balcony and take in the breathtaking mountain views!

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Chalet in Wintergreen Resort

The main living area features a local stone fireplace framed by large windows that allow natural light to fill the space. A comfortable couch and wooden coffee table create a welcoming atmosphere, complemented by decorative pillows and a small potted plant on the table.

4.92 out of 5 average rating, 130 reviews

Cozy Cabin+Walk to Ski *Hot Tub* Mtn Vibe

Renovated 3BR/2.5BA mountain home is just a short walk to ski slopes, hiking trails, and resort amenities. Enjoy a private hot tub, stone fireplace, deck with views, gas fire pit, and grill. Kids will love the bunk room and loft with Buck Hunter arcade & games. Smart TVs with streaming in main living and bunk room. Fully stocked kitchen + washer/dryer. Perfect for ski trips, hiking getaways, winery weekends, or a relaxing mountain escape

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Popular amenities for Wintergreen Resort family-friendly rentals

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Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.94 out of 5 average rating, 103 reviews

Designer Home w/ Incredible Views, Sleeps 16

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Cabin in Wintergreen Resort

The cabin is nestled among lush green trees, showcasing a multi-level structure with wooden balconies and a roof. A warm sunset casts a colorful glow over the exterior, highlighting its welcoming design and natural surroundings.

4.97 out of 5 average rating, 118 reviews

3 Levels · 3 Scenic Decks · Game Room · Hot Tub

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4.92 out of 5 average rating, 638 reviews

Farm stay in Nellysford

Spindle Hill Cottage: an Artist’s Farm, Hot Tub

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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.

4.97 out of 5 average rating, 121 reviews

Cozy 5-bedroom home for large gatherings.

FamilyKitchenOutdoor spaces

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.

4.89 out of 5 average rating, 161 reviews

Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat

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5.0 out of 5 average rating, 111 reviews

A spacious deck area is highlighted, featuring comfortable seating arrangements and a vibrant potted plant. The surrounding landscape includes lush greenery and distant mountains under a partly cloudy sky, creating an inviting outdoor retreat.

Farm stay in Roseland

116 Acre Private Retreat: Hot Tub, Pond, Goats

KitchenFamilyQuiet

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, 140 reviews

Designer Home: A+ Views HotTub Pool GameRoom Grill

FamilyKitchenCondition

4.94 out of 5 average rating, 180 reviews

The exterior of a lakeside log cabin showcases a large, sloped roof with wooden beams and expansive windows. A spacious deck is visible, featuring various seating options. The structure combines natural stone and wood elements, reflecting a rustic yet modern aesthetic.

Cabin in Faber

Lakefront Cabin w Stunning Curated Decor & Hot Tub

Indoor spacesFamilyBackyard

Family- and pet-friendly home rentals

4.98 out of 5 average rating, 228 reviews

A bright and airy living area is highlighted by large windows offering mountain views. A casual seating arrangement features a light-colored sofa and a wooden dining table surrounded by black chairs. Sliding glass doors provide access to an outdoor deck.

Apartment in Rockfish

Blue Ridge Bliss - For family & friends to enjoy!

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4.95 out of 5 average rating, 199 reviews

Ski-in/Ski-out Wintergreen Highlands Condo -Views!

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A spacious outdoor deck features a round dining table surrounded by tall chairs, complemented by a striped couch with soft cushions. An umbrella provides shade, while the scenic mountain views extend into the distance, above a layer of mist.

4.93 out of 5 average rating, 195 reviews

BlueRidge Getaway- Dog Friendly

KitchenIndoor spacesHiking

An inviting living space features a comfortable sectional sofa arranged around a round coffee table, complemented by a cozy rug. A gas fireplace is framed by white paneling, and large windows provide ample natural light while showcasing views of the surrounding landscape.

4.95 out of 5 average rating, 155 reviews

All-Season 2bd/2ba next to Spa view of Golf Course

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Superhost

A cozy living area features natural stone accents around a wood-burning fireplace. A small dining table with two chairs is positioned near large windows, allowing ample natural light. Green accent walls enhance the inviting atmosphere, while a comfortable seating area is visible nearby.

4.88 out of 5 average rating, 223 reviews

Tips Up: Cozy Slopeside Retreat w/ Fireplace

Indoor spacesFamilyDecor

The exterior of a two-story cabin houses warm wooden accents and large windows. The entrance features a welcoming set of wooden steps leading up to a balcony, surrounded by tall trees, with a concrete pathway leading toward it.

4.94 out of 5 average rating, 253 reviews

Eight Minute Walk to Everything

FamilyIndoor spacesOutdoor spaces

4.99 out of 5 average rating, 204 reviews

An interior view of the yurt features a circular ceiling with a skylight. Light wooden beams create a warm atmosphere. A kitchenette with a granite countertop is visible on the left, while a cozy seating area with a blue couch and decorative accents is displayed on the right. Natural light fills the space.

Yurt in Roseland

Mtn View~Bold Rock & DB 2mi~Nat. Park & Lake 10mi

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Apartment in Wintergreen Resort

A balcony is featured, showcasing two Adirondack-style chairs positioned for optimal mountain views. Sunrise illuminates the expansive horizon, with soft light reflecting off the distant landscapes. The floor is made of wood, enhancing the outdoor ambiance.

4.99 out of 5 average rating, 124 reviews

Endless Mountain Top Views from All The Way Up!

KitchenFamilyCleanliness

Family-friendly home rentals with a pool

A scenic view of rolling hills is captured at sunset, with soft hues of orange, pink, and purple coloring the sky. In the foreground, a glass of clear liquid rests on a wooden railing, enhancing the tranquil atmosphere.

4.99 out of 5 average rating, 185 reviews

3 BR 3 BA, 2 story condo in Highlands

FamilyIndoor spacesWalkability

Chalet in Wintergreen Resort

The living area is viewed from above, featuring a mix of seating options including a brown leather sofa and loveseat. A wooden dining table is positioned by the window, with light streaming into the space. A black and white rug anchors the seating area and a fireplace is visible.

4.94 out of 5 average rating, 192 reviews

Owl Bnb | Walkable to Slopes | Speakeasy Room

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4.91 out of 5 average rating, 165 reviews

Cozy Comfort with a View - Wintergreen Resort

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A cozy living area features a blue couch facing a wood-burning fireplace, with a flat-screen TV mounted above. A side chair provides additional seating. Natural light filters through large windows, illuminating a small coffee table adorned with a vase of yellow tulips.

5.0 out of 5 average rating, 104 reviews

Cozy Laurelwood condo - 1 min walk to pool

KitchenIndoor spacesGetting around

4.89 out of 5 average rating, 129 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

FamilyIndoor spacesSleep quality

A spacious living area features a wood-burning fireplace surrounded by light-colored walls. A comfortable couch, adorned with a welcoming throw pillow, faces a wooden coffee table. Natural light enters through large windows, offering views of the outdoor greenery.

4.93 out of 5 average rating, 254 reviews

Where the Trail Ends

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Cabin in Wintergreen Resort

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

Cozy Mountain Retreat- Walk to trails-EV charger

FamilyIndoor spacesLaundry