
George Washington National Forest Rentals
- From $527 per night (USD)
VRBO
\"SERENITY 4 ALL SEASONS\"
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
From the décor and furnishings to the beautiful views you will not want to leave. This 5 BR (3 queen beds, 1 full bed an ...
From $527 per night (USD)VRBO
- From $341 per night (USD)
Expedia
Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 11
Our beautiful mountain house has breathtaking sunset views and offers a short walk to the slopes and lodge of Wintergree ...
From $341 per night (USD)Expedia
- From $449 per night (USD)
VRBO
Spectacular Ski Chalet, 3 BR, 2.5 Bath, Great Location.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This chalet offers a spacious panaromic view, with a high wooden vaulted ceiling. Only 5 min away from ski slopes, ...
From $449 per night (USD)VRBO
- From $352 per night (USD)
Expedia
Time to Book for Spring and Summer...Amazing Views and 5-Star Amenities
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
While it may be getting hot where you live, at Wintergreen the spring and summer are much cooler and very pleasant. Wi ...
From $352 per night (USD)Expedia
- From $1014 per night (USD)
VRBO
Blue Ridge Mountain Retreat in Wintergreen
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 21
Welcome to Blue Ridge Mountain Retreat at Wintergreen! This amazing property is the newest addition to Wind Luxury Prope ...
From $1014 per night (USD)VRBO
- From $819 per night (USD)
Expedia
Luxury Mountain Lodge: Hot Tub and Incredible Mountain Views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Welcome to Harvest Moon Lodge & Retreat, where adventure and serenity meet. Nestled high on 9.2 acres in the heart of th ...
From $819 per night (USD)Expedia
- From $318 per night (USD)
VRBO
Cozy Condo at Wintergreen! Book now for The Ski Season!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This perfect little getaway is nestled into the hillside and centrally located within Wintergreen. Our place can serve ...
From $318 per night (USD)VRBO
- From $390 per night (USD)
Expedia
5 BR Wintergreen House w/ Game Room, 75” TV, Ping Pong, Foosball, Wet Bar & Deck
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 13
Enjoy mountain adventures with friends & family at this beautiful & newly renovated 5 bedroom mountain house located in ...
From $390 per night (USD)Expedia
- From $241 per night (USD)
VRBO
Top of Mountain 2 BR Condo close to hiking trails and scenic overlooks!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located at the top of Wintergreen Mountain, this spacious 2 bedroom 2 full baths condo gets close to all the action on t ...
From $241 per night (USD)VRBO
- From $174 per night (USD)
Expedia
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Ours is a 2-bedroom condo just 0.2 mile (3 minute walk) to the top of the Blue Ridge Express lift, in the Mountain Villa ...
From $174 per night (USD)Expedia
- From $538 per night (USD)
VRBO
2-Level Modern Home on 25 Wooded Acres with Amazing Mountain Views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Architect-designed home sits on a high ridge. Main living space optimizes dramatic views of Humpback Mountain. Covered ...
From $538 per night (USD)VRBO
- From $264 per night (USD)
VRBO
Tips Up: Cozy Slopeside Retreat w/ Fireplace (~100 Yards From The Slopes!)
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
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 h ...
From $264 per night (USD)VRBO
- From $1047 per night (USD)
VRBO
The newest and largest edition to the Wintergreen Retreat portfolio!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 23
The sky and blue ridge mountains loom large past floor-to-ceiling windows at this modern luxury ski lodge home on Winter ...
From $1047 per night (USD)VRBO
- From $304 per night (USD)
Expedia
Cozy 3-bedroom cabin located in Wintergreen Resort
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Capture all the beauty of Wintergreen's 4 seasons with this adorable property. Rustic 3-bedroom/2 full bath home sitting ...
From $304 per night (USD)Expedia
- From $299 per night (USD)
VRBO
Bear Necessities
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 8
Cozy Cabin minutes from Lexington or minutes from the Parkway, Endless Trails for hiking, hunting, creek for fishing alo ...
From $299 per night (USD)VRBO
- From $501 per night (USD)
Expedia
Wintergreen Home w/ Hot Tub, Deck & Mountain Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The ultimate Blue Ridge Mountain getaway awaits at this 3-bedroom, 2-bath vacation rental! This home boasts ski-in/out a ...
From $501 per night (USD)Expedia
- From $585 per night (USD)
VRBO
Above the Clouds! Perfect Escape for Families!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Breathe in the fresh mountain air when you stay at The Retreat at Wintergreen in the Blue Ridge Mountains. This updated ...
From $585 per night (USD)VRBO
- From $446 per night (USD)
Expedia
Incredible Mountain Views - Modern Four Bedroom Home - Five Minute Walk to Slope
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Pedlars Horizon, a serene mountain no home with spectacular mountain views. This cozy sanctuary is close to everything y ...
From $446 per night (USD)Expedia
- From $464 per night (USD)
VRBO
COZY SKI COTTAGE--SKI IN SKI OUT
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
the cottage has large front and rear decks, stairway to slopes, nice furniture and bedding, fully equipped kitchen, slee ...
From $464 per night (USD)VRBO
- From $444 per night (USD)
Expedia
Serene Hideaway with Views, 1 Mi to Hike & Ski!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
‘Treetop Getaway’ is surrounded by towering trees and breathtaking vistas, this 3-bedroom, 2-bath Wintergreen Resort esc ...
From $444 per night (USD)Expedia
- From $326 per night (USD)
VRBO
Cozy Mountain Retreat * Dog Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Immerse in nature’s beauty at the Bear Essentials Retreat located close to Wintergreen Resort, a year-round haven for ou ...
From $326 per night (USD)VRBO
- From $257 per night (USD)
Expedia
Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Directly on the slope of Eagle's Swoop our condo is in a central location to everything in the Wintergreen Resort! Enjoy ...
From $257 per night (USD)Expedia
- From $556 per night (USD)
VRBO
180 Degree Breathtaking Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Newly remodeled by new owner. Amazing views from the walk out wrap around terrace in Wintergreen Ski/Golf Resort. First ...
From $556 per night (USD)VRBO
- From $328 per night (USD)
Expedia
Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
SUMMER SPECIAL – LIMITED TIME OFFER Stay 2 nights and get your 3rd night for just $99 when you check in Sunday through ...
From $328 per night (USD)Expedia
- From $671 per night (USD)
VRBO
Beautiful Mountain Getaway• 5Bd, Wineries, Breweries, Golk, Hiking, New Arcade!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 16
Welcome to Stoney Creek Sanctuary, a 4,200 sq ft luxury retreat located in the highly sought-after Wintergreen Stoney Cr ...
From $671 per night (USD)VRBO
- From $862 per night (USD)
Expedia
Unbeatable Views Atop Wintergreen Resort
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Blue Ridge Heaven is located at an elevation of 3,850 feet atop Devils Knob – the highest point at Wintergreen Resort in ...
From $862 per night (USD)Expedia
- From $466 per night (USD)
VRBO
Book Now for Spring and Summer....Awesome Views and 5-Star Amenities
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
While it may be getting hot where you live, at Wintergreen the spring and summer are much cooler and very pleasant. Wi ...
From $466 per night (USD)VRBO
- From $320 per night (USD)
Expedia
Best views on Mountain! Breathtaking 5 Star condo! Book Summer and Fall now!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Completed remodeled with all new furniture and decor! This Non-Smoking, No-Pets condominium sleeps six: the master bedro ...
From $320 per night (USD)Expedia
- From $398 per night (USD)
VRBO
Wintergreen Resort Cabin: Near the Slopes!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Get away with your adventure-loving friends or family and stay at this chic 3-bedroom, 2.5-bath cabin nestled in the woo ...
From $398 per night (USD)VRBO
- From $332 per night (USD)
Expedia
House / hot tub/pet friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
You will find plenty of room to have family and friends with you to enjoy a peaceful vacation with the relaxing sounds o ...
From $332 per night (USD)Expedia
- From $711 per night (USD)
VRBO
Wintergreen Resort Retreat: Ski, Hike, Golf!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
From skiing at Wintergreen Resort to hiking the Appalachian Trail, this 4-bedroom, 3-bath house is perfect in any season ...
From $711 per night (USD)VRBO
- From $308 per night (USD)
Expedia
Relaxing 3 bdrm Mountain Cabin on Wintergreen Resort
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful cabin in the woods! Welcome to our home! This beautiful mountain cabin is located on the top of Wintergreen R ...
From $308 per night (USD)Expedia
- From $257 per night (USD)
VRBO
Escape to the Blue Ridge Mountains at Wine-tergreen!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Your perfect escape in the beautiful Blue Ridge Mountains! Enjoy a glass of the region's famous wines in front of the w ...
From $257 per night (USD)VRBO
- From $418 per night (USD)
Expedia
Breathtaking views! Beautifully decorated.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy a spring/summer getaway in our lovely three bedroom condo! Enjoy breathtaking views! Spend a day relaxing at the ...
From $418 per night (USD)Expedia
- From $238 per night (USD)
VRBO
Highlands Condo Views for days! Tons of details listed ⬇️☺️
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
2 bedroom 2 bath and a Queen size sofa bed. Sleeps up to 6 very comfortably. This is our second condo here as we’ve fal ...
From $238 per night (USD)VRBO
- From $279 per night (USD)
Expedia
Cozy Wintergreen Resort Condo: Walk to Ski Lifts!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Experience the unparalleled beauty and easy relaxation that Wintergreen Resort provides when you book this cozy 2-bedroo ...
From $279 per night (USD)Expedia
- From $590 per night (USD)
VRBO
4 BR cabin mins to trails & breweries pets welcome
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Feel right at home when you arrive at this lovely cabin at the very top of Wintergreen Resort mountain fresh ready for a ...
From $590 per night (USD)VRBO
- From $630 per night (USD)
Expedia
1 Mi to Slopes & Dining: Spacious Ski Getaway!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Pack your gear and head out to the mountains of Virginia for a stay at this 5-bed, 4-bath vacation rental, large enough ...
From $630 per night (USD)Expedia
- From $247 per night (USD)
VRBO
Beautiful, Remodeled Cottage in the Heart of Afton
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in the George Washington National Forest, Gracewood is a retreat from the mental and emotional activity of every ...
From $247 per night (USD)VRBO
- From $610 per night (USD)
Expedia
Bright Wintergreen Resort Home; Deck & Grill!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Escape to the mountains, and stay at this spacious and welcoming vacation rental in Wintergreen Resort! The 6-bedroom, 4 ...
From $610 per night (USD)Expedia
- From $549 per night (USD)
VRBO
One of the Best Views in Wintergreen!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
This unique property has some of the best views in Wintergreen. Make this your retreat after a day filled with hiking, ...
From $549 per night (USD)VRBO
- From $811 per night (USD)
Expedia
Mountain Home at Wintergreen Resort...in the heart of Virginia's wine country.
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Ski up the mountain in the late fall, winter and early spring . Enjoy golf, visiting wineries and breweries in the valle ...
From $811 per night (USD)Expedia
- From $250 per night (USD)
VRBO
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Be among the first to stay in this new construction! Fabulous condo with nice finishes and new furniture. Everything y ...
From $250 per night (USD)VRBO
- From $393 per night (USD)
Expedia
Private Riverfront Mountain Escape, 5BR Cabin + Firepit + game room.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Wake up to the sound of the Piney River flowing beneath towering hemlock, spend the afternoon tubing crystal-clear mount ...
From $393 per night (USD)Expedia
- From $454 per night (USD)
VRBO
Groups Welcome! Condo ~ 1 Mi to Wintergreen Resort
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Smart TV | Patio | EV Charger Across the Street (Charges Apply) Experience the quintessential four-seasons getaway at t ...
From $454 per night (USD)VRBO
- From $614 per night (USD)
Expedia
Luxe Private Getaway in the Heart of Wintergreen!
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
Enjoy the very best of Wintergreen! Walking distance to Appalachian Mountain trails & just minutes to the slopes at Wint ...
From $614 per night (USD)Expedia
- From $257 per night (USD)
VRBO
Creek Front Property! Spicewood Cabin Near Wintergreen and Crabtree Falls
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Spicewood cabin is located in the heart of scenic Nelson County. Our family owned property is nestled in the Blue Ridge ...
From $257 per night (USD)VRBO
- From $337 per night (USD)
Expedia
Amazing Mountain views - Ski In Ski Out - Wifi - fireplace - Pets OK
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
We are Slope-side with a full view to the North/East, Dobie Mountain Condominium, 2 Bedroom, 2 Bath, and recently instal ...
From $337 per night (USD)Expedia
- From $327 per night (USD)
VRBO
Mountaintop Wintergreen Resort Home w/ Deck, Views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Escape to the mountains with this spacious 4-bed, 3-bath Virginia vacation rental home! Tucked into the Wintergreen Reso ...
From $327 per night (USD)VRBO
- From $466 per night (USD)
Expedia
The Fairway Chalet Wintergreen
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to The Fairway Chalet, your perfect mountain retreat nestled in the heart of Wintergreen Resort. Perched alongsi ...
From $466 per night (USD)Expedia
- From $256 per night (USD)
VRBO
Updated! Cozy and clean two bedroom condo.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
It's cooler in the mountains! Come relax at this clean and cozy two bedroom condo. We are on the top floor but there ar ...
From $256 per night (USD)VRBO
- From $503 per night (USD)
VRBO
Gorgeous Rustic Mountain Cabin with Scenic Views! Welcome to Green Oak Cabin
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Instantly escape when you walk through the front door. The calmness of the cabin and the serenity of the mountains offer ...
From $503 per night (USD)VRBO
- From $256 per night (USD)
VRBO
Golf Course Views Golden Tee Pool Tennis Golf Hike
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
5min to ski slopes! Nestled in middle of Devils Knob Golf Course, unique 2,229sqft home features primary suite on first ...
From $256 per night (USD)VRBO
- From $340 per night (USD)
VRBO
Wintergreen Family Retreat- Each Br With Its Own Sliding Doors To A Deck
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to our mountain home at Wintergreen Resort! We fell in love with this house for the same reasons that we know yo ...
From $340 per night (USD)VRBO
- From $458 per night (USD)
VRBO
Designer Home: A+ Views HotTub Pool GameRoom Grill
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
5min drive to slopes. Sweeping views year round. Contemporary décor with rustic style. Retreats, romantic weekends or ad ...
From $458 per night (USD)VRBO
- From $337 per night (USD)
Expedia
View from the Top
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy breathtaking, panoramic mountain and valley views from this beautiful 2 bedroom, 3rd floor condo. The building's e ...
From $337 per night (USD)Expedia
- From $299 per night (USD)
VRBO
WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Best View of the Blue Ridge Mountains! Panoramic window views from the great room, dining area and kitchen. If you want ...
From $299 per night (USD)VRBO
- From $241 per night (USD)
Expedia
Couples Mountain Retreat
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to North Fork Cabin Rental's Hawks View! (Cabin will be closed for the winter January 5-March 15, 2026) We are ...
From $241 per night (USD)Expedia
- From $234 per night (USD)
VRBO
Deer Run - Mountain Getaway
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to North Fork Cabin Rental's Deer Run! (Cabin will be closed for the winter January 5-March 15, 2026) We are f ...
From $234 per night (USD)VRBO
- From $228 per night (USD)
Expedia
Rustic Mountain Retreat-Bear Paw
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to North Fork Cabin Rental's Bear Paw! (Cabin will be closed for the winter January 5-March 15, 2026) We are f ...
From $228 per night (USD)Expedia
- From $459 per night (USD)
VRBO
❤️️Stoney Creek Cottage❤️️Minutes to Wintergreen!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
***Professionally managed by FourEverySeason Properties*** Newly installed Level 2 Electric Vehicle Charger!! Charge y ...
From $459 per night (USD)VRBO
- From $358 per night (USD)
Expedia
Stoney Creek Cottage: Waterfront Hot Tub, Fire Pit
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
The perfect outdoor adventure is waiting for you at this charming home in Nellysford. This 2-bedroom, 1-bathroom vacatio ...
From $358 per night (USD)Expedia
- From $472 per night (USD)
VRBO
Whiskey Ridge - Luxury Mountaintop Family Retreat * Dog Friendly * Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Perched atop Wintergreen Resort, our luxurious retreat offers 2800 sq ft of space that comfortably sleeps 12 guests. Boa ...
From $472 per night (USD)VRBO
- From $635 per night (USD)
Expedia
Afton Escape! NEW Arcade, Wineries, Breweries
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 13
Welcome to Afton Cabin Home, a modern cabin retreat hidden in the mountains along the famed Nelson 151 Brew & Wine Trail ...
From $635 per night (USD)Expedia
- From $476 per night (USD)
VRBO
Cozy Cottage with beautiful Mountain View’s - close to wineries
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
The Cozy Cottage offers plenty of room to relax, with over 1,600 square feet of space divided amongst two floors. Define ...
From $476 per night (USD)VRBO
- From $339 per night (USD)
Expedia
Top-Rated Views – Near 151 Trail
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
A rental agreement and security deposit hold is required to rent this property. ⭐⭐⭐⭐⭐ Guest Favorite "One look at the v ...
From $339 per night (USD)Expedia
- From $257 per night (USD)
VRBO
Newly Updated Cozy Condo in the Heart of Wintergreen! Pet friendly.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Location, location, location- our cozy condo is short walk to everything! Park your car for the weekend and walk everyw ...
From $257 per night (USD)VRBO
- From $226 per night (USD)
Expedia
Cozy 'Nonny Cottage' Near Appalachian Trail!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 100
Unplug, unwind, and relax at this remote Vesuvius escape, located right off the Blue Ridge Parkway! This 2-bedroom, 1-ba ...
From $226 per night (USD)Expedia
- From $374 per night (USD)
VRBO
Family Friendly, Cozy Home on the Mountain Golf Course. All Necessities Included
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
We take extra cleaning precautions with covid 19. Newer listing to VRBO, super hosts on Airbnb with many reviews for yo ...
From $374 per night (USD)VRBO
- From $410 per night (USD)
Expedia
Mountain home close to resort, trails, breweries, & more!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
3-story single-family mountain chalet on a quiet street at Wintergreen Resort. King master en suite on third floor with ...
From $410 per night (USD)Expedia
- From $248 per night (USD)
VRBO
Cozy Mountain vibes 🏔️Dobie condos, - Steps from mountain Inn and chair lift!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Fresh air, cooler temps and Mountain View’s is like food for the soul. Our Dobie condo is situated just steps from the W ...
From $248 per night (USD)VRBO
- From $325 per night (USD)
Expedia
Wintergreen Resort Home w/ 2 Decks + Ski Access!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
All-season splendor awaits at this exemplary Roseland vacation rental! The 3-bedroom, 2-bath house delivers an upscale e ...
From $325 per night (USD)Expedia
- From $669 per night (USD)
VRBO
Opulent Retreat Amidst Blue Ridge`s Serenity * Dog Friendly * Hot Tub
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 18
Welcome to Whiskey Ridge Retreat, a cozy mountain getaway located within minutes of the ski lodge at Wintergreen Resort. ...
From $669 per night (USD)VRBO
- From $305 per night (USD)
VRBO
3 master bedroom condo in mountain resort
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful 1350 sqft condo with balcony views of trees and winter mountain views. Wood burning fireplace with free wood! ...
From $305 per night (USD)VRBO
- From $238 per night (USD)
VRBO
White Rock Cabin--1BR, ADA, kitchenette, fireplace
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Part of Love Ridge Mountain Lodging. Named for a popular nearby hiking and mountain biking trail, White Rock is a stand ...
From $238 per night (USD)VRBO
- From $297 per night (USD)
Expedia
Meadow Mountain Cabin at Love Ridge Mountain Lodging
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Named for a nearby mountain, Meadow Mountain is a stand alone, one bedroom, dog-friendly cabin with a jacuzzi tub and a ...
From $297 per night (USD)Expedia
- From $609 per night (USD)
VRBO
Afton Escape-New Arcade, Winery Brewery EV-Charger
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to Afton Stays. Make this mountain moment one to remember in this updated 4 bedroom, 2 bath home with 3 large f ...
From $609 per night (USD)VRBO
- From $279 per night (USD)
Expedia
You deserve it all! Awesome Views, Comfy Condo & Elevator!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Looking for an all inclusive family vacation? Look no further! We have your total four seasons get away solution with ...
From $279 per night (USD)Expedia
- From $497 per night (USD)
VRBO
Luxury Mountain - Labor Day Weekend Available. Book now for Winter Skiing
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Labor Weekend now available due to change in schedules. Some Oct weekends available. Nov month sold out. Book now for wi ...
From $497 per night (USD)VRBO
- From $938 per night (USD)
Expedia
Grand Chalet w/ Hot Tub - Near Wintergreen Resort
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Adventure and leisure combine at this luxurious 4-bedroom, 3-bathroom vacation rental home in Roseland, Virginia. Locate ...
From $938 per night (USD)Expedia
- From $488 per night (USD)
VRBO
Game Room, Sauna, Bonus Apartment Near Wintergreen Resort!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 20
Hillside Hideaway at Wintergreen Your perfect mountain retreat awaits in Virginia’s scenic Valley & Ridge Region! A Ho ...
From $488 per night (USD)VRBO
- From $353 per night (USD)
Expedia
RARE 3B/2B Mountain Top Condo Walk to the Slopes and Resturants! Slope Views!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Three Ridges- BEST LOCATION IN WINTERGREEN RESORT. This area has something for everyone. Wintergreen Resort Village, sh ...
From $353 per night (USD)Expedia
- From $361 per night (USD)
VRBO
3 Sisters - Historic 1840 Pre-Civil War Log Cabin with sauna, hot tub & firepit!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Three Sisters Log Cabin is an elegant, private, 1840's log cabin that happens to be one of only a few surviving two stor ...
From $361 per night (USD)VRBO
- From $174 per night (USD)
Expedia
Walking Distance to Ski Slopes! Cozy Condo that sleeps 4!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
A wonderful weekend escape no matter the time of year. Condo has been completely renovated in the heart of Wintergreen R ...
From $174 per night (USD)Expedia
- From $506 per night (USD)
VRBO
Stunning Wintergreen Resort Home: Ski & Golf!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Prepare to make lifelong memories on the mountain when staying at this beautiful Wintergreen Resort vacation rental! Whe ...
From $506 per night (USD)VRBO
- From $222 per night (USD)
VRBO
Stylish-Updated-Central -Walk to Slopes-Dogs OK!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Step into the allure of our fantastic Wintergreen near-slope condo, just a leisurely 4-min stroll away from the heart of ...
From $222 per night (USD)VRBO
- From $354 per night (USD)
VRBO
All-Season Fun! Wintergreen Resort Condo w/ Views
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 15
Rare find! True ski-in/ski-out at Wintergreen Resort! Make the most of your next Virginia mountain getaway at Slipper Sl ...
From $354 per night (USD)VRBO
- From $471 per night (USD)
Expedia
Blackwood Chalet: Hot Tub + 0.3 mile from Slopes
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
OUTDOORS: Private deck with hot tub, propane fire pit (4 chairs), and front porch ski closet. INDOORS: *NEW* 55" Roku S ...
From $471 per night (USD)Expedia
- From $313 per night (USD)
VRBO
Blue's Barn: Central to Wineries & Breweries
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
DOWNSTAIRS: Dining Room: counter height dining table with 4 stools Living Room: queen sleeper sofa, two side chairs, ...
From $313 per night (USD)VRBO
- From $770 per night (USD)
Expedia
Panoramic Views by Vineyards 4000 sf new home on 40 acs
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Enjoy the seclusion and beauty of the country with the convenient proximity to multiple wineries, breweries, distillerie ...
From $770 per night (USD)Expedia
- From $189 per night (USD)
VRBO
Wintergreen Resort Condo w/ Deck, 0.3 Mi to Slopes
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Plan for plenty of outdoor fun when you stay at this Wintergreen Resort vacation rental! With a vibrant interior, privat ...
From $189 per night (USD)VRBO
- From $228 per night (USD)
Expedia
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Starry starry nights are what you will experience. Great hiking off Blue Ridge Parkway, Appalachian Trail and on our pro ...
From $228 per night (USD)Expedia
- From $228 per night (USD)
VRBO
New cabin 1 mile from Blue Ridge Parkway. Minutes from Appalachian Trail
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Starry starry nights; sounds of Tye River gurgling over rocks; absolute quiet except for the sounds of nature. Wonderful ...
From $228 per night (USD)VRBO
- From $492 per night (USD)
Expedia
Ski-In/Ski-Out Wintergreen Resort Condo + Hot Tub!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Discover the serenity of Eagle's Court in Wintergreen Resort when you stay at this 2-bedroom, 1.5-bathroom vacation rent ...
From $492 per night (USD)Expedia
- From $849 per night (USD)
VRBO
Family Chalet at Wintergreen - Hot Tub, Sauna, Fire Pit, Game Room - Sleeps 16
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 17
Three families. Three floors. One house. Pleasant Point is a six-bedroom, four-bath mountain chalet at Wintergreen Res ...
From $849 per night (USD)VRBO
- From $448 per night (USD)
Expedia
Beautiful Mountain Getaway - Walk to Everything at Wintergreen!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
This beautifully renovated 3 BR / 2 BA mountain condo is very centrally located in the main Wintergreen village - steps ...
From $448 per night (USD)Expedia
- From $1111 per night (USD)
VRBO
Blue Ridge Bliss 9BR/6BA: 2 Homes Across the Street from each other! Sleeps 24
- Bedrooms:
- 6
- Bathrooms:
- 9
- Sleeps:
- 25
Discover Blue Ridge Bliss Across Two Homes: Experience the ultimate retreat with two homes across the street from one a ...
From $1111 per night (USD)VRBO
- From $304 per night (USD)
VRBO
Walk to Summer Music Festival: WTG Retreat Among the Trees
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Discover tranquility at Dobie Mountain Slopeside Retreat, a spacious 4 bed, 3 bath condo perfectly situated in an incred ...
From $304 per night (USD)VRBO
- From $302 per night (USD)
VRBO
Buena Vista - Your Panoramic Retreat - Million Dollar View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Discover serenity at Buena Vista, a charming 2BR, 2BA condo in Wintergreen Resort! This first-floor unit offers easy acc ...
From $302 per night (USD)VRBO
- From $360 per night (USD)
VRBO
CHARMING COUNTRY CABIN IN THE VIRGINIA BLUE RIDGE MOUNTAINS
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 11
Consider this cabin your home away from home while you visit our area.This enchanting property features 3 bedrooms - 3 w ...
From $360 per night (USD)VRBO




































































































