House holiday rentals in Wintergreen Resort

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, 181 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.

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.

A spacious great room features large windows, allowing natural light to fill the space while offering views of the surrounding trees. A comfortable sofa is positioned in front of a large television, and a dining table for eight is set nearby. Decorative accents include a chandelier and cozy armchairs.

4.95 out of 5 average rating, 110 reviews

Mntn View Pool Table Dogs OK Pool Tennis Golf Hike

7min WALK or 4min drive to slopes! Mountain estate amidst an aboral oasis with spectacular mountain views. Work remotely w/ FAST Wi-Fi. Close to wineries, breweries, farmers markets, hiking and Upper Shamokin Falls trail. ★3,160sqft of living ★Comfortably Sleep 10: K, K, K + bunk, D, sofa bed ★Dining table for 8 ★Great room w/ fireplace ★Incredible mountain view ★Pool table ★Movie room ★Dog and family-friendly Happy pet fee $187. Outdoor pool/tennis access included. Resort access not included.

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, 168 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.

5.0 out of 5 average rating, 36 reviews

Best Blue Ridge Views at Sunrise over Wintergreen

Spectacular Mountain Views & Sunrises Spend your days hiking over 30+ miles of trails (including the Appalachian Trail), driving the Blue Ridge Parkway, kayaking the lake in the summer, leaf peeping in the Fall, skiing one of the regions best mountains in the winter, or exploring Virginia's brewery and wine country. Whichever you choose, we're positive you'll enjoy your time at Sunrise over Wintergreen! New host family of beloved 250+ ★★★★★ 'Best View in the Blue Ridge from Biscuit's Porch'.

4.99 out of 5 average rating, 108 reviews

The unique octagonal house is framed by lush greenery, showcasing its distinctive architecture. A spacious deck offers a vantage point for enjoying unobstructed views of the surrounding landscape. Panoramic windows reflect the natural beauty of the Blue Ridge Mountains, inviting light into the living space.

Home in Afton

Mountain Overlook House - Blue Ridge Parkway

Unique octagonal house with stunning views of the Blue Ridge Mountains of Virginia. Located 2 miles from I-64, 15 minutes to downtown Waynesboro and an easy 25 min drive to Charlottesville and UVA. Open floor plan, perfect for gathering, and long-range 180 degree views from nearly every room. Fully equipped renovated kitchen. Quality linens and bedding. Rustic, yet modern decor. Home features large fireplace, outside fire pit, wifi, and board games galore. Stargazing and birdwatching heaven.

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.

4.95 out of 5 average rating, 239 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!

4.97 out of 5 average rating, 129 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.

A circular firepit is surrounded by four wooden Adirondack chairs, arranged thoughtfully on a gravel surface. Natural light filters through nearby trees, creating a serene outdoor seating area, perfect for gatherings or quiet reflections.

5.0 out of 5 average rating, 13 reviews

Blue Bear

Come and spend a relaxing or adventurous fall weekend in the gorgeous Blue Ridge Mountains. Blue Bear is a spacious and cozy home located at the Wintergreen Resort. You will be close to hikes, wineries, breweries, cideries, and great restaurants, . The home comfortably sleeps 7 guests with a comfortable living room and well stocked kitchen. There is outdoor space including a deck, propane firepit, and a propane grill located in an extremely peaceful and quiet natural setting.

4.94 out of 5 average rating, 104 reviews

Designer Home w/ Incredible Views, Sleeps 16

Welcome to Highlands Overlook, a designer-decorated home in the heart of Wintergreen. The deck is second-to-none, complete with hot tub, cedar barrel sauna, fire table, dining for 10, grill, smoker, pizza oven, and views everywhere. The light-drenched interior is equally impressive. With 6 bedrooms plus a private game room with pullout sofa, the home sleeps 16 comfortably. Plus, pet friendly! Managed by Chris at New School Hosting- click on his profile below to see more reviews.

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.

4.81 out of 5 average rating, 139 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!

The exterior of the home is surrounded by lush trees, featuring a spacious deck that extends around the building. A gravel pathway leads to the front steps, creating a welcoming entrance. Natural light filters through the trees, enhancing the peaceful setting.

4.9 out of 5 average rating, 189 reviews

Wintergreen Resort: Weeping Rock Retreat

Welcome to Weeping Rock Retreat in Wintergreen Resort. This 4 bedroom, 3 full bath home is certain to fit your individual or family needs. Tucked away on a hill off a quiet street is sure to give you a peaceful retreat to enjoy your vacation. Our home is located walking distance from the Upper Shamokin Trail which features a great scenic waterfall and easy trail for family. Great for large or multiple families and a short drive to the ski slopes.

Popular amenities for house rentals in Wintergreen Resort

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.99 out of 5 average rating, 172 reviews

A spacious deck is surrounded by greenery, featuring several black Adirondack chairs arranged around a firepit. The glass railing provides an unobstructed view of the outdoors, enhancing the inviting outdoor space.

Home in Nellysford

151Escape | 5☆ Group Fun! Game Room/Bar/Deck/4kTVs

5.0 out of 5 average rating, 112 reviews

A hot tub bubbles invitingly on a concrete pad in a spacious yard. Surrounding the tub is a well-maintained green lawn, with majestic mountains visible in the background. White Adirondack chairs are positioned nearby for relaxing moments outdoors.

Home in Nellysford

Spacious retreat: Game Room, Hot Tub & Fire Pit

Superhost

A spacious living area features a large sectional sofa adorned with colorful throw pillows. High, wooden ceilings are complemented by large windows that bring in natural light. A dining table and rustic décor are visible, creating a comfortable gathering space.

4.84 out of 5 average rating, 143 reviews

Hot Tub EV Charger Pool Table Dogs OK Tennis Golf

4.89 out of 5 average rating, 130 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

4.89 out of 5 average rating, 113 reviews

Home in Roseland

Wintergreen Resort | Pool, Hike, Golf, Hot Tub,

4.96 out of 5 average rating, 238 reviews

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

Private Pool Opens April 1 - All Year Hot Tub

4.94 out of 5 average rating, 162 reviews

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

Farmhouse on Working Vineyard

A picnic table is positioned on a grassy area, offering expansive views of rolling mountains under a partly cloudy sky. Lush greenery surrounds the table, creating a serene outdoor setting for relaxation or enjoying a meal.

4.98 out of 5 average rating, 47 reviews

Casa Perfecta

Weekly house rentals

4.97 out of 5 average rating, 29 reviews

Art & Soul: Sauna/Hot Tub & EV Charger/Hammocks

A cozy living room is featured, showcasing a wooden ceiling and a fireplace. A deep blue sectional sofa is arranged around a coffee table. Natural light floods in through a door leading to the balcony, revealing views of the surrounding trees and winter landscape.

4.98 out of 5 average rating, 45 reviews

Premiere 2 BR Getaway Ski In/Out Wintergreen Condo

The exterior of the cabin is presented, showcasing a two-story structure surrounded by trees. A welcoming porch with two chairs is visible at the entrance, and wide steps lead up to the front door. Natural light highlights the exterior's neutral tones.

5.0 out of 5 average rating, 12 reviews

The SnowHouse HotTub Dogs OK Firepit Creek PacMan

5.0 out of 5 average rating, 16 reviews

Coziest Condo 1st floor, walk to the Patio Terrace

A spacious great room features a stone fireplace as its focal point, surrounded by large windows that offer views of the sunset and surrounding trees. Leather couches and a glass coffee table complement the modern decor, while a plush ottoman provides extra seating.

4.94 out of 5 average rating, 72 reviews

Panorama Peak Lodge-4 bedroom with sweeping views

5.0 out of 5 average rating, 52 reviews

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

Wintergreen Mountain Retreat

4.98 out of 5 average rating, 46 reviews

Wintergreen 5BR | Hot Tub | Sauna | Firepit

5.0 out of 5 average rating, 20 reviews

Mountain View | Hot tub | Sleeps 14

Private house rentals

4.92 out of 5 average rating, 59 reviews

Cabin · Hot Tub + Sauna · Arcade · Game Porch

Superhost

A wooden sign displaying the number '190' stands at the forefront, surrounded by a forest floor covered in leaves and rocks. In the background, a multi-level cabin can be seen, partially obscured by trees, with decks extending from the upper levels.

4.84 out of 5 average rating, 37 reviews

Hillside Hideaway

An inviting living area features a large sectional couch and two patterned armchairs surrounding a modern coffee table. A mounted flat-screen TV is positioned above a stone fireplace, with large windows allowing natural light. A bar area with seating provides additional gathering space.

4.89 out of 5 average rating, 64 reviews

Renovated 4+BR luxury townhome @ the Mountain Top!

The airy living room features a stone gas fireplace beneath a large mounted TV, offering a cozy focal point. Large windows frame the view of the outdoors, allowing natural light to fill the space. Ample seating is provided by a sectional couch and accent chairs.

4.96 out of 5 average rating, 52 reviews

Welcome to Winterhaven! 5BR/4BA .5mi from lodge!

The living room features high ceilings with exposed beams and large windows showcasing the surrounding trees. A light gray sofa and armchairs provide comfortable seating, while a round coffee table sits at the center. A jute area rug adds texture to the hardwood floor.

4.95 out of 5 average rating, 65 reviews

Treeloft 17: Ski in/ski out – EV charger – 3BR/3BA

5.0 out of 5 average rating, 37 reviews

White Wolf Chalet at Wintergreen

A snow-covered slope is seen, with skiers and snowboarders enjoying the day. Trees line the edge of the hill, providing a natural border. In the background, multiple buildings are visible, reflecting a ski resort atmosphere under a clear blue sky.

4.93 out of 5 average rating, 45 reviews

Wintergreen Condo Ski In Ski Out