Holiday rentals with a patio in Wintergreen Resort

Holiday 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, 252 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!

5 out of 5 average rating, 234 reviews

A cozy cottage, named the 'Sugah Shack,' is nestled amidst the rolling hills of the Blue Ridge Mountains. The white exterior contrasts with the vibrant greenery surrounding the property, while the majestic mountains form a picturesque backdrop against a bright, partly cloudy sky.

Cottage in Afton

Cozy Mountain Cottage on Brew/Wine Trail-King Bed

Welcome to the Sugah Shack, a cozy, beautifully appointed new construction cottage nestled in the foothills of the Blue Ridge Mountains! Located midway on the Brew Ridge Trail, but 500 yards off the byway, so guests have a quiet retreat. Perfect for romantic getaways, destination telework space, or families exploring this outdoor paradise community. Stunning property boasts beautiful vistas with sweeping 300-degree mountain and a year-round calendar of outdoor activities. GAS FIREPLACE/FIREPIT

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.

4.89 out of 5 average rating, 213 reviews

Tips Up: Cozy Slopeside Retreat w/ Fireplace

The mountains are calling and you must go. Well, you don't have to, but we think it's a good idea. Make Tips Up your home while you're away. With slopeside views, a cozy and comfortable ambiance, and close proximity to skiing (only 100 yards from the slopes!) and hiking, this 1B/1BA condo is the perfect getaway for outdoor enthusiasts seeking a mountain escape. Relax at nearby breweries and wineries with unbeatable views, and return to your condo to enjoy the amenities of 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, 117 reviews

Endless Mountain Top Views from All The Way Up!

Our warm and inviting condo combines amazing proximity to hiking with to-die-for views of the Blue Ridge Mountains and the horizon 75 MILES distant! Our condo sits a mere 400-yd walk from the closest hiking trail and also has direct access to the ridge line walking area - perfect place for a morning stroll! This updated and modern mountain themed space features: ✸ Newly renovated! ✸ Stocked modern kitchen! ✸ Two full bathrooms! ✸ Helix Hospitality Mattresses!! ✸ Cozy Fireplace w/ wood provided!

5 out of 5 average rating, 154 reviews

A charming cottage is nestled among lush green grass and surrounded by trees. Its metal roof and white siding are complemented by well-maintained shrubbery. Dappled sunlight filters through the tree branches, creating a serene outdoor ambiance.

Cottage in Covesville

Historic cottage with stunning mountain views

Welcome to Rose Cottage in picturesque Albemarle County, where you'll enjoy expansive 360-degree views of the mountains surrounding historic Cove Lawn Farm. Relax in the tranquil rural setting or stroll more than two miles of comfortable walking paths that wind through 25 acres of stream-lined hayfields. From Rose Cottage, you're just minutes from the best local cideries, distilleries, and wineries including Pippin Hill Farm & Vineyards. Easy 20-minute drive to UVa and 22 minutes to Monticello.

5 out of 5 average rating, 121 reviews

A newly constructed cottage is set on a private mountain lot, featuring a light-colored exterior and a sloped roof. A spacious screened porch with wooden steps is visible, surrounded by green grass and trees. Natural landscaping enhances the peaceful environment.

Cabin in Roseland

Mountain Hideaway Cottage

Perfect for couples or families. Tucked away on its own private mountain acreage with stream access. Large screened porch for talking into the night or enjoying your morning coffee. Ask about same day after 5pm discount! Less than 2 miles to Devil's Backbone and Bold Rock. Minutes to Blue Ridge Parkway,Appalachian Trail, Wintergreen, breweries, wineries, cideries, restaurants, horseback riding, hiking, mountain lakes, & antique shopping. Gas fireplace. 1G WiFi & SMART TV. Fire pit and wood.

A private balcony features wooden railings, with a light dusting of snow on the ledge. Lush pine trees stand prominently in the background, contrasting against a clear blue sky and hints of distant landscape, contributing to a serene outdoor viewing experience.

4.96 out of 5 average rating, 167 reviews

2-min drive to resort, Outdoor HOA pool opens 5/25

Peaceful, recently renovated mountain-top retreat. Relax or work from home. End your day with a hike or spa treatment around the corner—linger with a glass of wine at sunset. It’s all only a 2 minute walk from the front door. Welcome to our mountain home! 2-3 min drive from ski lifts/resort, hiking Free firewood (seasonal) Family games & smart TVs (no cable) for movie night (must sign into your own subscriptions) Smartlock entry Stair-free entry *outdoor HOA pools CLOSED for season

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.

4.95 out of 5 average rating, 194 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.

Superhost

An outdoor seating area features a sectional couch adorned with cushions, positioned around a fire table. The space is surrounded by trees, with a patterned area rug underneath. A small table holds a potted plant and a bottle, creating a relaxed ambiance.

Cabin in Wintergreen Resort

4.91 out of 5 average rating, 103 reviews

Modern Cabin with Hot tub and Sauna

Welcome to Blue Ridge Hollow! This designer-decorated cabin in the heart of Wintergreen has one of the best outdoor spaces in the area. Relax in the hot tub or cedar barrel sauna, then enjoy a meal at the oversized outdoor table or sip wine around the firepit. The updated kitchen is fully stocked and open to the living room and sun-drenched dining room. 3 bedrooms are masters, the others share a bathroom, and the downstairs game room can be a 6th bedroom. Plus, pet friendly!

Cabin in Wintergreen Resort

A screened porch features a modern fire table surrounded by two comfortable chairs. Large glass panels provide unobstructed views of the surrounding trees, allowing natural light to fill the space while maintaining a connection to the outdoor scenery.

4.99 out of 5 average rating, 108 reviews

Cozy Mountain Retreat- Walk to trails-EV charger

Escape to a bright, spacious mountain retreat just minutes from the slopes and walkable to scenic trails. Perfect for families and groups, this open concept, light-filled home features a cozy fireplace, stocked kitchen, and screened porch for relaxing after adventure-filled days. EV charger available to guests during your stay. Sleeps comfortably with 2 king ensuites, a queen bedroom, and a fun bunk room - ideal for skiing, hiking, and wine country getaways.

A living room features a stone fireplace with a wooden mantel. A clock is mounted above, and decorative items are displayed on the mantel. Hardwood flooring complements the room's layout. The space is open to a kitchen area, visible in the background, with light cabinets and appliances.

4.97 out of 5 average rating, 117 reviews

Wintergreen Resort King bed, Fire place, 2 Bd/2 Br

Forget your worries in this spacious and serene space. Condo has been completely renovated and can be enjoyed all year round! Located between the Wintergarden Spa, the Nature Foundation and the Devils Knob Sports Center (golf, tennis and fine dining restaurant) Stone Ridge neighborhood is centrally positioned to most of the Resort amenities. 5 min drive to slopes 5 mins to Market 15 to Devils Backbone 3 mins to Devils Knob golf course

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 out of 5 average rating, 100 reviews

Cozy Laurelwood condo - 10 min walk to slopes

This beautiful 1-bedroom, 1-bath Laurelwood condo is perfectly located just a short walk from the pool, market, coffee shop, restaurants, and the Wintergreen Conference Center. Inside, you’ll find a fully equipped kitchen, a cozy wood-burning fireplace (with complimentary firewood), and a spacious king-size bed. Step outside to your private deck and enjoy the peace of the surrounding forest—an ideal retreat for relaxation and comfort.

Popular amenities for Wintergreen Resort Holiday Houses with Outdoor Verandahs

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with a patio

4.96 out of 5 average rating, 54 reviews

A craftsman-built apartment is nestled among lush greenery, surrounded by mountain forests. Vibrant flowers frame the foreground, leading to the wooden structure with a metal roof. The natural landscape features rolling hills and a clear blue sky, creating an inviting outdoor setting.

Apartment in Tyro

Crabtree Falls Mountain Hollow Guesthouse

The living room features a spacious seating arrangement with two sofas, a cozy armchair, and a round coffee table. Large windows frame expansive views of the Blue Ridge Mountains, inviting natural light into the airy space. A dining table for six is visible in the background.

4.93 out of 5 average rating, 45 reviews

Big Condo*Luxe Baths*Sweeping Views*Walk2Chairlift

The cozy living area is furnished with a brown leather sofa and two armchairs. A glass coffee table sits on a soft rug, and artwork adorns the wall above the couch. Natural light enters through sliding doors, which lead to the outdoor area.

4.94 out of 5 average rating, 17 reviews

Weller’s Retreat at Stone Ridge

An outdoor dining setup on a spacious deck features several plates with a breakfast spread, including eggs, fruit, and pastries. A steaming cup and a glass of juice are present. In the background, a telescope is positioned to enjoy the scenic mountain view under a cloudy sky.

4.98 out of 5 average rating, 44 reviews

Luxury Slope-View Condo w/ Sauna | Dogs OK

Superhost

4.89 out of 5 average rating, 9 reviews

Amazing Views! Wintergreen Ground Level Condo

A cozy living area features a neutral color palette with a comfortable sectional sofa and a second soft sofa. A wooden coffee table is centered between the seating. Artwork is displayed on the wall above the fireplace, complemented by decorative items on the mantel.

5 out of 5 average rating, 12 reviews

Cozy base camp for blue ridge adventures

A scenic view showcases lush greenery with trees framing a winding pathway. The landscape features rolling hills in the background under a bright, partially cloudy sky, offering a tranquil atmosphere for outdoor exploration.

4.92 out of 5 average rating, 12 reviews

Fantastic views/WalktoResort/PupFriendly!

4.92 out of 5 average rating, 13 reviews

Eagles Court Ski In/Out Condo

Holiday House Rentals with a Verandah

4.97 out of 5 average rating, 114 reviews

Home in Roseland

Stargaze on 12 Acres: Hot Tub 55"TV Fire Pit Grill

Home in Wintergreen Resort

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.

4.93 out of 5 average rating, 43 reviews

Wren Time

4.95 out of 5 average rating, 43 reviews

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

Hot Tub! Wintergreen Resort!

4.98 out of 5 average rating, 102 reviews

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

Cottage at Mountain View Meadow

Home in Wintergreen Resort

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.

5 out of 5 average rating, 34 reviews

White Wolf Chalet at Wintergreen

4.97 out of 5 average rating, 112 reviews

A vast expanse of green grass stretches across the foreground, framed by lush orchard trees. Rolling hills covered with foliage rise in the background, under a clear blue sky dotted with soft white clouds, creating a serene rural atmosphere.

Home in Afton

Perfect getaway among the orchards of Batesville

4.96 out of 5 average rating, 26 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

4.99 out of 5 average rating, 116 reviews

A serene view of the Blue Ridge Mountains is presented, showcasing rolling hills blanketed in mist during sunrise. The sky is painted with soft pastel shades of orange and pink, highlighting the natural beauty of the surrounding landscape.

Home in Afton

Mountain Mama- Amazing Views! + Hot Tub!

Holiday condos with a patio

A cozy living area features a sleek, brown leather sofa positioned across from a wood-burning fireplace. A glass coffee table is centered on a patterned rug, while a mounted television hangs above, all set against a vibrant green accent wall with textured design.

4.77 out of 5 average rating, 98 reviews

Cozy 1-bedroom Condo with Fireplace Near Ski Slope

A spacious living area features large windows that provide expansive views of the surrounding landscape. Comfortable seating includes a sectional couch and a reclining chair, arranged around a wooden coffee table. A sleek stone fireplace and a mounted television add to the contemporary decor.

4.96 out of 5 average rating, 46 reviews

Wintergreen Mountain Views - Diamond in the Slopes

A balcony view reveals a vast expanse of rolling green mountains under a clear blue sky. A square table is surrounded by two woven chairs, inviting guests to enjoy the serene landscape of the Blue Ridge Mountains and Rockfish Valley.

4.92 out of 5 average rating, 25 reviews

Condo with Valley Views!

An outdoor deck features a comfortable seating area with plush cushions and a coffee table. Two glasses of wine rest atop the table, surrounded by panoramic views of the Blue Ridge Mountains bathed in soft hues of sunset.

5 out of 5 average rating, 59 reviews

Buena Vista Panoramic Retreat: Million Dollar View

A deck features two comfortably arranged chairs with cushions, overlooking expansive views of the Blue Ridge Mountains. Clear skies are visible, and the natural landscape extends into the distance, highlighting the serene outdoor setting.

4.97 out of 5 average rating, 33 reviews

Recently updated - views of the Blue Ridge Mtns

4.93 out of 5 average rating, 80 reviews

The living room features a spacious sectional sofa and two armchairs, arranged around a wooden coffee table. A wood-burning fireplace is located against a green wall, complemented by softly illuminated shelves. Natural light filters through windows, creating a cozy atmosphere.

Condo in Roseland

Nature’s Haven 1 Bedroom Condo Wintergreen Resort

A cozy living area features a stone fireplace with a wooden mantle. Natural light enters through large windows framed by light curtains. Comfortable seating includes a brown sofa with decorative pillows and a stylish orange chair. An adjacent dining table offers space for meals.

5 out of 5 average rating, 24 reviews

3 Ridges 3 min walk to slopes,besides inn,King bed

A sunset view is captured over the mountains, with the sun dipping below the horizon, casting warm hues across the sky. Dense trees frame the scene, providing a sense of tranquility amid the natural landscape.