Wintergreen Resort vacation rentals

5 out of 5 average rating, 119 reviews

A charming cottage is framed by lush green lawns, with two prominent stone chimneys rising from its exterior. The landscape is complemented by mature trees and distant mountains under a bright blue sky, creating a serene rural atmosphere.

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.

Villa in Wintergreen Resort

4.96 out of 5 average rating, 80 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!

Two chairs are positioned near a large panoramic window, offering expansive views of the Blue Ridge Mountains. A small table sits between the chairs, adding a touch of convenience to the inviting corner. Soft light filters through the sheer window treatments.

4.97 out of 5 average rating, 119 reviews

2 bdrm/2 full bath Best Views of Blue Ridge Mtns.

Best View of the Blue Ridge Mountains! Panoramic window views from the great room, dining area and kitchen. If you want to get a closer look step out on the observation deck to see the beautiful mountains and ski slopes (seasonal). Patio furniture is on the deck to enjoy morning sunrises and evening sunsets. All new stainless steel appliances in kitchen, Freshly painted throughout. 2 bedroom 2 bath Lots of activities to do at the Wintergreen Resort all year long. Year round resort activities.

5 out of 5 average rating, 13 reviews

A spacious living area is highlighted by a stone fireplace, surrounded by large windows with natural light. A dining table is set for several guests, with elegant plates and glassware arranged on its surface. Inviting seating options are visible in various styles.

Home in Roseland

Hot Tub! Wintergreen Resort!

Check out our 5 star reviews on VRBO and "cozy cabin at wintergreen dot com". Prepare to escape and relax at our three bedroom, two bath cabin, nestled atop the Blue Ridge mountains, a short walk (5 Houses) to the Devils Knob Overlook. This luxury resort retreat is perfect for couples getaway, wedding, family vacation or girls weekend. Spend the day brewery hopping down the famous Route 151, where you have over twelve wineries and breweries to visit. Or enjoy hiking, skiing, spa & golfing.

A spacious living area features a large, comfortable sectional sofa adorned with various throw pillows. A coffee table with a wooden tray sits in the center, while warm light is provided by multiple stylish lamps. Large windows invite natural light and offer views of the surrounding landscape.

4.86 out of 5 average rating, 107 reviews

Hot Tub Pool Table Dog OK Tennis Golf Shuffleboard

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 $150. 8min walk or 3min drive to ski.

The living area features a woodburning fireplace as the focal point, surrounded by comfortable seating that includes two chairs and a spacious gray couch. A round ottoman sits at the center, with large windows offering views of the outdoor landscape, softened by sheer curtains.

4.88 out of 5 average rating, 163 reviews

Wander Lodge: Golf, Spa, Wine, or just a getaway

Comfortable 3-BR, 2-bath condo on Devil's Knob Golf Course. Comfortably sleeps 6-7, 2 Queen beds, 1 full bed, futon, & comfy couch. Woodburning fireplace; balcony, small newly renovated kitchen w/stove, dishwasher, microwave, Keurig, tea kettle,coffee maker, crockpot; Smart TV w/ Streaming apps(free only); Walking distance to hiking trails, nature center, DeVine Wine & Coffee shop, tennis facilities, & the lovely wintergreen spa; less than 1 mile from Mountain Inn & restaurants & shops.

4.97 out of 5 average rating, 203 reviews

Cabin in Afton

Inn at the Woods: Updated Cabin w/Mountain Views

Fall in love with the charm of this recently updated ‘Hansel & Gretel’ style cabin located on Castle Rock Mountain. This cabin has 3 bedrooms + a loft, with a total of 4 queen beds. Hike and explore the 20+ acres or relax on the large multi-tiered deck and fire-pit area while soaking in the mountain sunsets. Enjoy nearby dining, breweries, or wineries, the historical town of Charlottesville, or spa, golf, tennis, and skiing at the Wintergreen Resort - both just a short drive away.

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.

4.94 out of 5 average rating, 132 reviews

BlueRidge Getaway- Dog Friendly

Relax and enjoy spectacular top-floor mountain views from the deck. This recently renovated unit is at the top of the mountain close to many hiking trails. Visit the Wintergreen village, with its restaurants and shops, with a 5 minute drive or an easy hike through the woods. You also have access to Rhodes Farm and Chestnut Hills pool. This condo is convenient to Devils Backbone, Bold Rock, and the litany of other breweries, cideries, distilleries, and restaurants. Dogs welcome!

A clean, inviting swimming pool is surrounded by lush greenery and tall trees. Comfortable lounge chairs are positioned nearby, and sunlight reflects off the water, creating a serene atmosphere. The pool area is enclosed with a wooden railing for safety.

4.98 out of 5 average rating, 134 reviews

1 bedroom condo, hiking, breweries, wineries

Enjoy the mountains in the spring & summer enjoy hiking or a swim in the heapool! 1BR 1BA centrally located in Wintergreen 5 minute walk to Wintergreen resort Close to many hiking trails Enjoy the many breweries & wineries in the area Mountaintop Market is across the street 1 Bedroom 1 Bath & New queen sleeper sofa Stocked kitchen, cookware, spices & cooking oils Premium coffee & assorted tea Private furnished patio Wood burning fireplace, all you need for a quiet getaway

4.88 out of 5 average rating, 193 reviews

A hot tub is positioned in the foreground, showcasing bubbling water. In the background, a vibrant pink tree stands against a clear blue sky, surrounded by green grass and blooming shrubs. String lights are suspended above, enhancing the outdoor space.

Barn in North Garden

Private - Mountain View's & Hot tub! PETS OK

Beautiful views just off Route 29, only 10 minutes from UVA, and tucked near the area’s finest wineries and top attractions. This intimate, luxury barn suite offers a private setting with 1 king bedroom, 1 bathroom, and an open-concept living room and kitchen featuring a cozy fireplace, queen pullout sofa bed, and single cot for extra guests. Unwind and relax on the back patio with breathtaking sunsets, hot tub, grill and a firepit — all fully yours to enjoy during your stay.

4.94 out of 5 average rating, 62 reviews

Hot Tub Mntn Views Pool Tennis Golf Hiking 52"HDTV

Impressive 3-story mountain estate. Ideal for family retreats and adventurous getaways. Features HOT TUB. Wineries, breweries, farmers market, and walk to hiking trails. 4min dive to slopes! ★Comfortably sleeps 10: K, K, Full, Twin bunk beds, Sleeper sofa in loft ★Great room with stone fireplace ★Dining table for 8 ★FAST Wi-Fi ★Two 52" HDTVs ★Wrap around decks ★Fire Pit ★Hot Tub ★Plenty of parking Seasonal outdoor pool/tennis access. Resort access not included.

An expansive deck is illuminated by string lights, featuring a central firepit surrounded by four wooden chairs. In the background, a warm glow reflects off a salt-water hot tub, creating a cozy outdoor atmosphere.

5 out of 5 average rating, 27 reviews

5-star Luxury 4BR/4BA Lodge w/ HotTub!

Rustic, 5-star lodge great for a Guys or Gals weekend, weddings and family gatherings. Well-appointed with 4 cozy bedrooms each with their own private en suite bathroom. Unleash your inner chef in the gourmet kitchen w/ sun-filled dining area. Spread out in the 2-story family room with gas fireplace. Head outside to the expansive deck overlooking the 14th hole on Devils Knob golf course and enjoy the hot tub and firepit.

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Popular amenities for Wintergreen Resort vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Wintergreen Resort's top sights

The Nature Foundation at Wintergreen16 locals recommend

Ravens Roost Overlook22 locals recommend

Upper Shamokin Falls Trail31 locals recommend

Devil’s Knob Grill5 locals recommend

Wintergarden Pool & Spa6 locals recommend

Shamokin Springs Nature Preserve11 locals recommend

Ski-in/ski-out vacation rentals in Wintergreen Resort

A cozy living area features a stone fireplace with a wooden mantel, displaying potted plants and candles. A modern gray sectional sofa is positioned nearby, complemented by a rustic rocking chair adorned with a colorful cushion. The warm tones of the wooden ceiling create an inviting ambiance.

5 out of 5 average rating, 16 reviews

Wintergreen condo ski-in/ski-out

4.97 out of 5 average rating, 127 reviews

Mtn/Firework Views from Private Deck ~ King Suite

Chalet in Wintergreen Resort

The main living area features soaring ceilings and a local stone fireplace as the focal point. Comfortable seating is arranged around a wooden coffee table. Large windows bring in natural light, and a smart TV is positioned to one side, enhancing the space's functionality.

4.91 out of 5 average rating, 103 reviews

Brown Bear Lodge, walk to the slopes!

Townhouse in Wintergreen Resort

The living area features a cozy red sofa and a wooden coffee table, complemented by a colorful area rug. A circular wooden dining table with four chairs sits nearby, illuminated by natural light from the large windows. A stone fireplace adds a rustic touch to the atmosphere.

4.94 out of 5 average rating, 181 reviews

Fantastic home in an ideal location, dogs welcome!

A well-furnished living room features a large sectional sofa alongside a cozy chair. A coffee table sits in the center, while a stone fireplace adds warmth. Glass doors provide access to a balcony with dining furniture, highlighting scenic mountain views.

4.96 out of 5 average rating, 178 reviews

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

A spacious living area is highlighted by a stone fireplace with a mounted TV above. Natural light flows through the surrounding large windows, and wooden beams enhance the rustic feel. A staircase leads to an upper loft area, with comfortable seating arranged nearby.

4.97 out of 5 average rating, 195 reviews

Ski-In/Ski-Out Renovated Chalet on Lower Tyro

Cabin in Wintergreen Resort

A cabin exterior is showcased, featuring a deck with various chairs and a table for outdoor dining. Large windows reflect natural light, complementing the surrounding greenery. A stone feature is visible below the deck, adding organic texture to the scene.

4.99 out of 5 average rating, 133 reviews

Family Friendly Home with All Necessities Included

An open living area features a comfortable sofa with decorative pillows and a coffee table. A dining counter with tall stools is visible, alongside a well-equipped kitchen that includes a refrigerator and microwave. Wall art complements the muted tones of the room.

4.9 out of 5 average rating, 142 reviews

Cozy Comfort with a View - Wintergreen Resort

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Other great vacation rentals in Wintergreen Resort

4.88 out of 5 average rating, 16 reviews

Bluebird Mtn Home ~Dog Friendly ~ ~No step entry~

An inviting living area features a stone fireplace, surrounded by comfortable seating. Large windows allow natural light to fill the space, providing views of the outdoors. A dining table is set nearby, complementing the warm wooden floors and open layout.

4.75 out of 5 average rating, 4 reviews

Hilltop Escape At Wintergreen

A vibrant sunset casts warm hues over rolling mountains, visible in the distance. A solitary tree stands gracefully on the lawn, framing the scenic view. The open area features well-maintained grass, inviting moments of relaxation while enjoying the natural beauty.

4.88 out of 5 average rating, 67 reviews

Gorgeous Sunrises (The Cliffs)

4.83 out of 5 average rating, 23 reviews

An outdoor deck is presented, featuring a composite wood surface. Four black chairs are arranged around a glass-topped table, offering a space for relaxation. Lush greenery and distant mountains create a serene backdrop, with soft twilight hues illuminating the scene.

Home in Waynesboro

Modern 5BR Home | Spacious Getaway in the Valley

5 out of 5 average rating, 25 reviews

Two green Adirondack chairs are positioned on a gravel area beside a gently flowing stream. Nearby, a black fire pit adds a cozy element to the outdoor space, surrounded by trees and fallen leaves.

Cabin in Montebello

Blue Ridge Cabin 5

Cabin in Wintergreen Resort

An open-concept living area is showcased with vaulted ceilings and an abundance of natural light. A brown leather sofa sits opposite a wooden coffee table, surrounded by dining chairs. A staircase leads to the upper level, which is adorned with framed wall art and decorative ski equipment.

4.87 out of 5 average rating, 79 reviews

Dog Friendly - Backs to Golf - Spacious Deck

4.94 out of 5 average rating, 50 reviews

Tall trees with bare branches border a serene creek, their shadows stretching across a grassy area. The water flows gently, reflecting the sky above. A carpet of fallen leaves adds texture to the ground, indicating the seasonal changes in the landscape.

Home in Lyndhurst

Cozy Creekside 2-bedroom home.