House vacation 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, 180 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, 167 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'.

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.

4.99 out of 5 average rating, 108 reviews

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.

4.88 out of 5 average rating, 153 reviews

Home in Roseland

Blue Ridge Mt retreat steps off Appalachian Trail

Escape to this stunning 3-story Wintergreen mountain retreat, steps from the Blue Ridge Parkway and Appalachian Trail. Featuring a lighted circular driveway and three private porches, it offers ample space for relaxation. The top floor includes two bedrooms and a large bath. The main level boasts a den, kitchen, master bedroom, and a fully stocked kitchen with a 10-seat dining table. The bottom floor features another master bedroom and a bunk room. Unwind by the cozy fireplace or hot tub!

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, 128 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.

The exterior view showcases a modern blue house set against a backdrop of lush green hills. A wooden deck extends from the home, providing access to outdoor space. The gravel driveway is lined with a rustic split-rail fence, enhancing the natural feel of the surroundings.

4.97 out of 5 average rating, 156 reviews

Llama Loft | Fire Pit | Fenced Yard | Brew Trail

Escape to a spacious, colorful home off the Brew Ridge Trail with oversized windows, mountain views, and plenty of room for groups or couples. Cook in a stocked kitchen, then relax by the fire pit or grill out and unwind on the deck while the dogs enjoy the fenced in yard. Accessible bedrooms and bathrooms on the main floor make it easy for everyone to enjoy. Perfectly located near Wintergreen Resort, Skyline Drive, breweries, wineries, vineyards, hiking, biking, and golf.

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 Wintergreen Resort house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a hot tub

5.0 out of 5 average rating, 240 reviews

Home in Greenwood

Gorgeous Modern Mountain Home + Blue Ridge Views

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.

4.83 out of 5 average rating, 143 reviews

Hot Tub EV Charger Pool Table Dogs OK Tennis Golf

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.

5.0 out of 5 average rating, 112 reviews

Game Room+Screen Porch+Hot Tub+Fire Pit on 151

4.89 out of 5 average rating, 113 reviews

Home in Roseland

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

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.

4.98 out of 5 average rating, 131 reviews

Mountain Mama- Amazing Views! + Hot Tub!

A spacious dining area features a large wooden table set for twelve, surrounded by black chairs. A decorative light fixture hangs above, and a green accent wall complements the room. Shelving displays decorative items, adding character to the inviting space.

4.97 out of 5 average rating, 108 reviews

Twin Ponds | King Beds, Hot tub, Game Room, 75" TV

An inviting outdoor space features a hot tub surrounded by a spacious deck, with mountain views in the background. A large dining table with wooden chairs is positioned indoors, complemented by a fully-equipped kitchen visible in the adjacent area. A cozy fire pit with adirondack chairs provides a warm setting.

4.99 out of 5 average rating, 155 reviews

Hot Tub, Firepit, Mtn Views, Walk to Coffee & Park

A spacious deck features a hot tub and a dining area set for six. Scenic views of a vibrant sunset and surrounding landscape create a calming atmosphere, while the wooden decking enhances the connection to nature.

4.95 out of 5 average rating, 144 reviews

Sycamore Shade: 151 House, HOT TUB, Mountain Views

House rentals with free parking

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, 44 reviews

Premiere 2 BR Getaway Ski In/Out Wintergreen Condo

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

5.0 out of 5 average rating, 9 reviews

Home Outdoor Fire Pit Arcade, Scenic Helipad Views

A stone patio area is set against a backdrop of lush greenery, featuring a rectangular table and two matching benches. Flagstone pathways lead to the seating area, while surrounding garden elements enhance the outdoor space. The area offers an unobstructed view of the hillside.

5.0 out of 5 average rating, 16 reviews

Ski-in ski out!

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!

5.0 out of 5 average rating, 20 reviews

Mountain View | Hot tub | Sleeps 14

An outdoor deck is equipped with a propane firepit surrounded by a dark block, offering a cozy gathering space. Comfortable, upholstered seating is arranged for relaxation, with expansive views of trees and hills in the background, showcasing the natural beauty of the mountainous landscape.

4.99 out of 5 average rating, 68 reviews

Stunning Views, Hot Tub, Impeccable Design

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

House rentals with a pool

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.

4.89 out of 5 average rating, 130 reviews

Mountain Bauhaus | Sleeps 8 | Amenities | Grill

Superhost

Home in Waynesboro

4.78 out of 5 average rating, 210 reviews

Downtown Riverview Castle with Pool and Hot Tub!

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.

4.94 out of 5 average rating, 161 reviews

Farmhouse on Working Vineyard

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

4.88 out of 5 average rating, 50 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!

The exterior of the house features a modern design with a combination of gray siding and a shingled roof. Surrounded by trees, the entryway is framed by steps leading to the front door, with a spacious driveway visible in the foreground.

4.9 out of 5 average rating, 61 reviews

Luxury House on Mountain Golf Course near Slopes

A spacious outdoor living area features a modern hot tub with glowing blue water, surrounded by a custom-built bar. Soft lighting from overhead lanterns adds a cozy ambiance, while a large screen TV is mounted nearby, overlooking the tranquil wooded surroundings.

4.98 out of 5 average rating, 66 reviews

Luxury Oasis | Hike, Lakes, Golf | Pet friendly!

The exterior of a two-story house is shown, featuring a combination of stone and wood paneling. Surrounding trees provide natural shade. A set of steps leads to the entrance, which is framed by a covered porch. A pathway and deck are visible on the side.