House holiday 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.

FamilyValueGetting around

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, 184 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.

FamilyValueGetting around

A spacious mountain estate is framed by bare trees in a serene winter setting. The exterior features a mix of light and dark wood siding, a welcoming front porch with seating, and an American flag gently waving. A gravel pathway leads up to the home.

4.96 out of 5 average rating, 112 reviews

Walk to Ski! Mntn View DogsOK Pool Table Fireplace

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.

LocationValueIndoor spaces

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, 170 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.

FamilyLocationView

5.0 out of 5 average rating, 39 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'.

LocationValuePets

4.99 out of 5 average rating, 111 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.

FamilyLocationDecor

4.97 out of 5 average rating, 63 reviews

Luxury 4100+ sqft designer resort-style home in Wintergreen with top and unique amenities: • 6 bedrooms, 4.5 baths, 12 beds including 4 King beds • Game & media rooms: Pool table, shuffleboard, arcade machines, 100-inch TV, & home theater • Dining seating: Indoor (10-seat & 6-seat tables) + 3 bar stools • Outdoor spaces: 10-seat dining, 8-seat couch, fire pit, grill; 6-seat couch • Golf course-front with Mountain & Valley views • Backyard oasis: Hot tub, barrel sauna, cold plunge

FamilyLocationLaundry

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!

FamilyLocationComfort

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!

ValueFamilyHeating

4.97 out of 5 average rating, 130 reviews

Cliffs Edge - It’s Pumpkin Spice Time!

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.

LocationFamilyComfort

4.94 out of 5 average rating, 109 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.

ValueLocationDecor

4.94 out of 5 average rating, 104 reviews

Pickleball | 2 Homes | Sleeps 19 | 151 Brew Trail

Nelly's Retreat is located in the lovely rolling hills of Nellysford, VA. The property includes 2 spacious homes that sleep up to 19 guests. Our unique property is perfect for bachelor/bachelorette groups, reunions, business retreats, and multi family getaways. Nelly's Retreat is centrally located to over a dozen wedding venues and is just off the Route 151 Wine/Brew Trail. We are minutes away from Shenandoah National Park and Wintergreen Resort!

LocationFamilyNearby

Popular amenities for Wintergreen Resort house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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.

4.99 out of 5 average rating, 173 reviews

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

FamilyValueView

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, 113 reviews

Spacious retreat: Game Room, Hot Tub & Fire Pit

LocationFamilyLayout

4.89 out of 5 average rating, 113 reviews

The bright living area features tall windows allowing natural light to illuminate the space. A fireplace creates a focal point, while comfortable seating is arranged around it. A staircase leads to the upper level, and outdoor views are visible through the glass doors.

Home in Roseland

Fall Retreat | King Beds | Hot Tub | Hiking

ValueFamilyBarbecue

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, 132 reviews

Mountain Bauhaus | Sleeps 8 | Amenities | Grill

ValueFamilyKitchen

4.94 out of 5 average rating, 163 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

FamilyLocationLayout

4.96 out of 5 average rating, 240 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

FamilyLocationHiking

4.92 out of 5 average rating, 49 reviews

Mid-Century Modern • Game Room • Hot Tub

ValueFamilyNearby

5.0 out of 5 average rating, 32 reviews

Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14

LocationFamilyCondition

Weekly house rentals

A spacious living area is showcased, featuring a large kitchen island with dark cabinetry. Large windows invite natural light, revealing views of surrounding trees. Comfortable seating areas are arranged nearby, emphasizing an open-concept design that connects kitchen and lounge spaces.

5.0 out of 5 average rating, 59 reviews

Top of the Mountain Hideaway with Hot Tub!

ValueFamilySleep quality

A spacious living area features large windows allowing natural light to flow in. Comfortable seating includes a dark leather sofa and a cozy armchair, surrounded by a round coffee table atop a soft rug. Art posters decorate the walls, and a television is positioned on a console beneath.

4.95 out of 5 average rating, 40 reviews

Luxe Cliff House Retreat: Hike, Sip, Relax

LocationFamilyCheck-in

5.0 out of 5 average rating, 23 reviews

Mountain View | Hot tub | Sleeps 14

FamilyLocationAccuracy

4.97 out of 5 average rating, 30 reviews

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

LocationFamilyCondition

A spacious living area features a high vaulted ceiling with exposed wooden beams and a stone fireplace. Large windows allow natural light to fill the room, highlighting comfortable seating arrangements and decorative accents. A chandelier hangs above, complementing the rustic design.

4.93 out of 5 average rating, 30 reviews

Summit Serenity - Walk To Slopes and Restaurants

FamilyValueGetting around

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!

ValueFamilyLong stay

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

LocationFamilyWalkability

5.0 out of 5 average rating, 13 reviews

Blue Bear

FamilyLocationAccuracy

Private house rentals

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, 46 reviews

Wintergreen Condo Ski In Ski Out

ValueFamilyParking

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.

4.88 out of 5 average rating, 33 reviews

Charming Wintergreen resort home

ValueFamilyCleanliness

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!

FamilyLocationSleep quality

A spacious mountain house is nestled among tall trees, surrounded by lush greenery. A gravel driveway leads to the entrance, showcasing the home's unique architectural features, including large windows that offer natural light.

5.0 out of 5 average rating, 21 reviews

Greyhaven II

FamilyLocationAmenities

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.

4.95 out of 5 average rating, 73 reviews

Panorama Peak Lodge-4 bedroom with sweeping views

LocationFamilyKitchen

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, 44 reviews

Wren Time

LocationValueCondition

A wooden deck features several Adirondack chairs arranged around a fire pit, providing a cozy setting for relaxation. Expansive views of the surrounding mountains and valleys are visible beyond the railing, with a mix of trees and rolling hills extending into the distance.

4.87 out of 5 average rating, 86 reviews

Big Black Bear Lodge | Luxury 5BR Mountain Oasis

LocationFamilyKitchen