
George Washington National Forest Rentals
- From $838 per night (USD)
VRBO
Spacious 3BR 3BA Pet Friendly Resort Condo
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Escape to our spacious 3-bed, 3-bath mountain condo, perfect for families or groups. Enjoy cozy evenings by the gas fire ...
From $838 per night (USD)VRBO
- From $507 per night (USD)
Expedia
Ledges 78 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Ledges Valley View Retreat Take in beautiful valley views from this top-floor, end-unit condo in Ledges at Wintergreen ...
From $507 per night (USD)Expedia
- From $465 per night (USD)
VRBO
Tanners Ridge 21 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Tanners Ridge Mountain Escape Enjoy a relaxing retreat in this 2-bedroom, 2-bath condo in Tanners Ridge, located in Win ...
From $465 per night (USD)VRBO
- From $507 per night (USD)
Expedia
Overlook 29 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Overlook Scenic Mountain Retreat Take in the beauty of Wintergreen from this 2-bedroom, 2-bath condo in the Overlook co ...
From $507 per night (USD)Expedia
- From $667 per night (USD)
VRBO
Ledges 72 with Wintergreen Advantage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Ledges Spacious Mountain Escape Enjoy a relaxing Wintergreen getaway in this spacious 3-bedroom, 3-bath condo at Ledges ...
From $667 per night (USD)VRBO
- From $667 per night (USD)
Expedia
Ledges 52 with Wintergreen Advantage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Ledges Peaceful Mountain Retreat Escape to a peaceful mountain getaway in this spacious 3-bedroom, 3-bath condo at Ledg ...
From $667 per night (USD)Expedia
- From $465 per night (USD)
VRBO
Laurelwood 48 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Laurelwood Mountain Escape Escape to the mountains in this inviting 2-bedroom, 2-bath retreat in Laurelwood at Wintergr ...
From $465 per night (USD)VRBO
- From $604 per night (USD)
Expedia
Northridge 06 with Wintergreen Advantage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Northridge Tranquil Mountain Retreat Escape to the tranquility of Wintergreen Resort in this spacious 3-bedroom, 3-bath ...
From $604 per night (USD)Expedia
- From $604 per night (USD)
VRBO
Stoneridge 81 with Wintergreen Advantage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Stoneridge Cozy Mountain Escape Enjoy a relaxing mountain getaway in this spacious 3-bedroom, 3-bath condo at Stoneridg ...
From $604 per night (USD)VRBO
- From $604 per night (USD)
Expedia
Stoneridge 70 with Wintergreen Advantage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Stoneridge Spacious Mountain Retreat Settle into a spacious mountain getaway in this 3-bedroom, 3-bath condo at Stoneri ...
From $604 per night (USD)Expedia
- From $1028 per night (USD)
VRBO
Fully Loaded 8BR in Wintergreen! Sleeps 23
- Bedrooms:
- 4
- Bathrooms:
- 8
- Sleeps:
- 23
Welcome to Crawfords Escape, a designer-decorated 8BR 4500 sf chalet in scenic Wintergreen that sleeps 23. Outside, enjo ...
From $1028 per night (USD)VRBO
- From $526 per night (USD)
Expedia
Newly Remodeled 4BR/4.5BA Golf Front Townhome. Pet Friendly!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Completely Remodeled Golf Front Townhome | Walk to Ski Shuttle Stop, Spa & Fitness Center | Pet-Friendly Experience the ...
From $526 per night (USD)Expedia
- From $506 per night (USD)
VRBO
Escape to Wintergreen Resort! Our pet & kid-friendly 2BR/2BA townhome is steps from skiing, dining & the Market. Hike, ski, swim, or sip at nearby wineries & breweries—adventure awaits year-round!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Wintergreen Resort is a fantastic, all season destination, with adventures for everyone! We are a pet and kid friendly, ...
From $506 per night (USD)VRBO
- From $405 per night (USD)
VRBO
Family-favorite rental nestled in the woods at the top of the Wintergreen Resort
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
The Blue Ridge Mountains are calling you to this 3-level, 4 bed/3 bath home for an epic getaway! A family-favorite renta ...
From $405 per night (USD)VRBO
- From $472 per night (USD)
VRBO
The Honey Den - Your Family's Summer Retreat - Outdoor Pools, Nature, Adventure
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 11
Welcome to The Honey Den - a warm 5BR, 4.5BA mountain home designed for slow mornings, golden-hour decks, and easy toget ...
From $472 per night (USD)VRBO
- From $467 per night (USD)
Expedia
Little Haven Cottage: Walk to Meade Tasting
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Escape to the serenity of the Blue Ridge Mountains with a stay at our cozy, well-appointed cottage located directly on t ...
From $467 per night (USD)Expedia
- From $462 per night (USD)
VRBO
Serenity Cabin-Woodland Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Serenity Cabin: Your Perfect Woodland Retreat Nestled among the trees, this recently renovated timber-framed ...
From $462 per night (USD)VRBO
- From $505 per night (USD)
Expedia
Amazing Mountain Views, Hot Tub and Close to Wineries and Breweries
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Sit back, relax, and soak in the views. The Rockfish Retreat is nestled in the foothills of the Blue Ridge Mountains, ri ...
From $505 per night (USD)Expedia
- From $536 per night (USD)
VRBO
Wren Time, Wintergreen Mountain Retreat with Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
A Mountain home nestled in the Blue Ridge Mountains with breathtaking valley views and mesmerizing sunrises! The propert ...
From $536 per night (USD)VRBO
- From $488 per night (USD)
VRBO
Authentic Log Cabin-
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Come enjoy our beautifully decorated authentic log cabin which provides the perfect setting for your weekend get-a-way o ...
From $488 per night (USD)VRBO
- From $330 per night (USD)
VRBO
Endless Mountain Top Views from All The Way Up!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Our warm and inviting condo combines amazing proximity to the ski slopes with to-die-for views of the Blue Ridge Mountai ...
From $330 per night (USD)VRBO
- From $241 per night (USD)
Expedia
Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Rosie's Retreat (FKA: Ro's Retreat) Come enjoy this cozy 3 bedroom/3 bath condo located on the 18th hole of Devils Knob. ...
From $241 per night (USD)Expedia
- From $398 per night (USD)
VRBO
Modern Wintergreen Cabin with Hot Tub, Sauna
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
Welcome to Blue Ridge Hollow! This designer-decorated cabin in the heart of Wintergreen has one of the best outdoor spac ...
From $398 per night (USD)VRBO
- From $393 per night (USD)
Expedia
Coin Cottage farmhouse on 151 Trail in Nelson County
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This 1946 farmhouse has been remodeled this recently. Talk about location!!! This home is located within 1 mile of Silve ...
From $393 per night (USD)Expedia
- From $387 per night (USD)
VRBO
Leaf-Peeping at Oak Ledge! Trails+Tastings+Peace
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
<p>You'll find ski privileges, a kayak, and more on site at this family-friendly cabin. There's convenient onsite parkin ...
From $387 per night (USD)VRBO
- From $645 per night (USD)
Expedia
4BD Modern Cabin | Patio, Game Loft, Golf Course View
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to the Castor Cabin - an impeccably decorated home in the heart of Wintergreen! This recently renovated space an ...
From $645 per night (USD)Expedia
- From $1506 per night (USD)
VRBO
Insane Mountain Views - New Listing
- Bedrooms:
- 9
- Bathrooms:
- 7
- Sleeps:
- 18
One of the largest homes in Wintergreen with 7 bedrooms and 10 bathrooms. The floor-to-ceiling windows offer a sunrise ...
From $1506 per night (USD)VRBO
- From $472 per night (USD)
Expedia
Pet Friendly Cozy Mountain Retreat-sleeps 10!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
A quiet and relaxing escape for up to 10 people only a 2 minute drive to the Wintergreen Village. Parking for up to 3 ve ...
From $472 per night (USD)Expedia
- From $715 per night (USD)
VRBO
Stunning Views, Hot Tub, Impeccable Design
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Ryder's Ridge, a designer-decorated home on a quiet street in Wintergreen with amazing mountain views! Watch ...
From $715 per night (USD)VRBO
- From $174 per night (USD)
Expedia
Ski-In/Ski-Out Comfy Condo
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Great condo for a couple or for a small family. Condo is a ski-in/ski-out on the ground floor-no stairs to tackle! Enter ...
From $174 per night (USD)Expedia
- From $1084 per night (USD)
VRBO
Luxury mountain home Ski- in-Ski out
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 9
Gorgeous Blue Ridge Mountain Weekend Escape! Well mannered Pets welcomed with owners permission. Must ask ahead. We welc ...
From $1084 per night (USD)VRBO
- From $180 per night (USD)
Expedia
Slope Side Suite
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Escape to the mountains and cozy up at this incredibly central cabin at Wintergreen Resort (a short walk to ski slopes). ...
From $180 per night (USD)Expedia
- From $664 per night (USD)
VRBO
Blue Ridge Cabin · 3 Levels · 3 Scenic Decks · Music Game Room · Hot Tub· Arcade
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to the Rockstar Ridge, a 3,300 sq. ft. cabin retreat perched atop a ridge near Wintergreen Resort in Virginia's ...
From $664 per night (USD)VRBO
- From $195 per night (USD)
Expedia
Wintergreen 1bed Condo, Walk to slopes, close to Hiking, Breweries, Wineries
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Walking distance to the slopes 🎿🗻 located in Wintergreen New 1BR 1BA centrally located in Wintergreen Enjoy the beau ...
From $195 per night (USD)Expedia
- From $373 per night (USD)
VRBO
Wintergreen Resort Retreat w/ Skiing Access!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Kick back and relax at this charming 3-bedroom, 3-bath Wintergreen Resort condo! Tucked away in the Blue Ridge Mountains ...
From $373 per night (USD)VRBO
- From $192 per night (USD)
Expedia
Snug Wintergreen Resort Studio: Ski In & Out!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
The ultimate Blue Ridge Mountain adventure awaits with this lovely cabin-inspired studio as your home base! Nestled in W ...
From $192 per night (USD)Expedia
- From $361 per night (USD)
VRBO
Embrace the mountain lifestyle in this delightful true ski-in/ski-out condo in Wintergreen!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 5
Escape to the beauty of Wintergreen Resort in every season! Our cozy 1-bedroom, 2-bath condo is just steps from the slop ...
From $361 per night (USD)VRBO
- From $381 per night (USD)
Expedia
Spacious + Serene Mtn Top Escape, 4 En Suites
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to our mountain top home, just minutes from the heart of the resort, connected to walking trails, and with spect ...
From $381 per night (USD)Expedia
- From $674 per night (USD)
VRBO
Welcome to our stunning 3-bedroom, 2-bathroom house nestled in the heart of Wintergreen, Virginia.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to this enchanting 3-bedroom, 2-bathroom home located in the picturesque Wintergreen, VA. This delightful mounta ...
From $674 per night (USD)VRBO
- From $641 per night (USD)
Expedia
Roudy’s Retreat: Secluded Mountain Cabin with Hot Tub and Private Pond
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 10
Escape to this spacious retreat with a hot tub and everything you need to get away. The wooden interior will take you to ...
From $641 per night (USD)Expedia
- From $1272 per night (USD)
VRBO
Pet-Friendly Snowflake Inn: Cozy Retreat with Sauna, Jacuzzi & Family Fun!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
The Snowflake Inn is a family friendly home located in the coveted Blackrock district in the heart of the Wintergreen Re ...
From $1272 per night (USD)VRBO
- From $323 per night (USD)
Expedia
Spy Run Hideaway is a 1/2 mile from the Blue Ridge Parkway & pet friendly!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Spy Run Hideaway is truly a one-of-a-kind experience that is quiet and secluded on 17 acres that is nestled in the Blue ...
From $323 per night (USD)Expedia
- From $560 per night (USD)
VRBO
Hickory Hideaway- 5 BR 4 BA with game room and indoor fire place
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to the Hickory Hideaway! This 5 BR, 4 BA home is located in the heart of Wintergreen Resort. The home features ...
From $560 per night (USD)VRBO
- From $448 per night (USD)
Expedia
3 Ridges Vista. Stunning mountain views, renovated home, 2 mins to ski slopes
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to 3 Ridges Vista. Stunning views of the Blue Ridge Mountains including the famous Three Ridges peaks. This full ...
From $448 per night (USD)Expedia
- From $720 per night (USD)
VRBO
Luxe Wintergreen Resort Escape w/ Hot Tub!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Treat your family to a mountainside retreat and book this 4-bedroom, 3-bath Roseland vacation rental! This amenity-packe ...
From $720 per night (USD)VRBO
- From $573 per night (USD)
Expedia
Bright & Modern 5 BR Wintergreen Home; Minutes from Hiking, Skiing, and Wineries
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
Welcome to Hiker’s Haven! Located in Wintergreen Resort, Hiker’s Haven is the perfect retreat for all seasons. After a ...
From $573 per night (USD)Expedia
- From $203 per night (USD)
VRBO
Idyllic Wintergreen Condo w/ Resort Amenities
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
With easy access to resort amenities and the great outdoors, this Wintergreen Resort vacation rental is the perfect spot ...
From $203 per night (USD)VRBO
- From $291 per night (USD)
VRBO
Private One Bedroom by Mountain Stream
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Cabin Barnwood is a very private one bedroom, with a nice patio and creek. The bedroom has a queen pencil poster bed, a ...
From $291 per night (USD)VRBO
- From $278 per night (USD)
VRBO
Logwood Cabin Pre Civil War
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Pre-Civil War Log cabin Cabin Creekwood is a family-owned business providing relaxing getaways in the Blue Ridge Mounta ...
From $278 per night (USD)VRBO
- From $373 per night (USD)
VRBO
Pet Friendly Three Bedroom in Blue Ridge Mountains
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Oakwood is a large three bedroom, two bath cabin, all on one level. The master bedroom contains a queen bed, plus a s ...
From $373 per night (USD)VRBO
- From $292 per night (USD)
VRBO
Pet Friendly Two Bedroom in Blue Ridge Mtns
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
A very comfortable two bedroom, Mountainwood gives plenty of room to spread out. The main room is nice and open, includ ...
From $292 per night (USD)VRBO
- From $424 per night (USD)
Expedia
Cozy Modern Cabin near Wintergreen and Bold Rock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy your stay away from town with this cozy modern cabin located in the foothills of Wintergreen. The home is equipped ...
From $424 per night (USD)Expedia
- From $756 per night (USD)
VRBO
6 BR home, NEW HOT TUB, EV Charger.Walk to slopes! Close to wineries & breweries
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
*NEW HOT TUB* 5/6 BR spacious home for friends and family retreat with EV Charger Level 2! We offer a 10% discount on th ...
From $756 per night (USD)VRBO
- From $410 per night (USD)
Expedia
Adventure Awaits
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 13
Summary: Welcome to Adventure Awaits at Wintergreen Resort, your ultimate destination for year-round excitement nestled ...
From $410 per night (USD)Expedia
- From $216 per night (USD)
VRBO
Wintergreen Resort Vacation Rental w/ Balcony!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the beauty of Wintergreen Resort, VA, and indulge in a memorable stay at this 2-bedroom, 2-bathroom vacation re ...
From $216 per night (USD)VRBO
- From $302 per night (USD)
Expedia
Wintergreen Resort Vacation Rental w/ Pool Access!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
No matter the season, you’ll have easy access to endless outdoor adventures when you stay at this cozy Wintergreen Resor ...
From $302 per night (USD)Expedia
- From $213 per night (USD)
VRBO
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Pet-Friendly One Bedroom Condo on a Scenic Golf Course Indulge in relaxation at this tranquil Wintergreen haven. No mat ...
From $213 per night (USD)VRBO
- From $419 per night (USD)
Expedia
Serene Wintergreen Retreat, Nestled in the Trees
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to our cozy Wintergreen cabin in the trees! You'll truly feel at peace with nature on the three levels of decks ...
From $419 per night (USD)Expedia
- From $205 per night (USD)
VRBO
Afton escape centrally located on the brew trail
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Centrally located on the brew trail, this home is a short drive to the local wineries, breweries and distilleries, as we ...
From $205 per night (USD)VRBO
- From $502 per night (USD)
Expedia
Welcome to Winterhaven! 5BR/4BA .5mi from lodge!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to Winterhaven! Recent rental with new furniture, TVS, and updates throughout and flat paved driveway. Locat ...
From $502 per night (USD)Expedia
- From $503 per night (USD)
VRBO
Coastal Farmhouse Getaway!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Take it easy at this unique and tranquil getaway. This fully renovated historic farmhouse sits on 4 acres on Windmill Po ...
From $503 per night (USD)VRBO
- From $490 per night (USD)
Expedia
Your Mountain Cabin Getaway Awaits!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
EVERYTHING YOU NEED! Exquisitely furnished and decorated private cabin retreat in the mountain woods just minutes from t ...
From $490 per night (USD)Expedia
- From $504 per night (USD)
VRBO
Whispering Pines with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy the fresh mountain air and picturesque forested surroundings when you stay at Whispering Pines, a secluded 3-bedro ...
From $504 per night (USD)VRBO
- From $746 per night (USD)
Expedia
Orchard House with Wintergreen Advantage
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
A Beautifully Appointed Mountain Retreat at Wintergreen Orchard House is a distinctive five-bedroom, six-and-a-half-bath ...
From $746 per night (USD)Expedia
- From $504 per night (USD)
VRBO
Black Dog Treehouse with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Do you hear that? The mountains are calling, and this is your perfect home away from home. The Black Dog Treehouse is a ...
From $504 per night (USD)VRBO
- From $792 per night (USD)
Expedia
Luxury Designer Home, Dome and Top amenities
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 16
Welcome to Wintergreen - Mountain View Retreat! Discover the latest listing in Wintergreen – a spacious mountain retreat ...
From $792 per night (USD)Expedia
- From $385 per night (USD)
VRBO
Hot Tub Pool Pac Man Foosball Dogs OK Tennis Golf
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
4min to ski, walk to trails! Endless activities: apple picking, breweries/wineries, hiking, lake, horseback, golf, tenni ...
From $385 per night (USD)VRBO
- From $460 per night (USD)
Expedia
Hot Tub Sauna EV Charger Golden Tee Pool Tennis
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 14
5min to ski slopes! New hot tub and EV charger. Perfect for 2-3 families. After day of adventures, gather for sunset on ...
From $460 per night (USD)Expedia
- From $404 per night (USD)
VRBO
Sip 'n Dip: Hot Tub Foosball Pool Table Ping Pong
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Easy access to Wintergreen Resort, hiking trails, tennis, golf, and breweries/wineries. Great for families and groups. ...
From $404 per night (USD)VRBO
- From $676 per night (USD)
Expedia
Cozy House at Wintergreen with hot tub/firepit/fireplace & all amenities included and pool access!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to our cozy 4-bedroom, 3.5-bathroom home in Wintergreen Resort, VA. Enjoy a spacious living room with a fireplac ...
From $676 per night (USD)Expedia
- From $505 per night (USD)
VRBO
Mountain House Overlooking Rockfish Valley
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Unique octagonal house offering incredible views of the Blue Ridge Mountains of Virginia. Located 2 miles from I-64, 15 ...
From $505 per night (USD)VRBO
- From $634 per night (USD)
Expedia
Luxury Wintergreen 5BR • Hot Tub • Sleeps 16+ • Dog Friendly
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 16
Welcome to "Above the Clouds", your year-round retreat in the heart of Wintergreen. Our spacious house, nestled just min ...
From $634 per night (USD)Expedia
- From $374 per night (USD)
VRBO
Twin Ponds: King Beds, Hot tub, Gameroom, 75\" TV, Foosball, Air Hockey, PingPong
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
About this space Welcome to Twin Ponds, a beautifully appointed & fun-filled mountain house in Wintergreen Resort's Ston ...
From $374 per night (USD)VRBO
- From $334 per night (USD)
Expedia
Cozy Cabin in the Wintergreen Retreat Collection of Fine Homes
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to bespoke, rustic luxury in the heart of Wintergreen Resort! Come enjoy our beautifully decorated, authentic l ...
From $334 per night (USD)Expedia
- From $627 per night (USD)
VRBO
Escape the Heat • 10° Cooler Mtn Oasis • Hot Tub • Fire Pit • 4 Ensuite BRs
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
PROPERTY OVERVIEW: Escape the summer heat at 3,800 feet in the Blue Ridge Mountains! Often up to 10° cooler than the va ...
From $627 per night (USD)VRBO
- From $238 per night (USD)
Expedia
Wintergreen Ski Resort Condo w/ Golf Access!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Days spent shredding the slopes and cozy nights by the fireplace await when you stay at this charming 2-bedroom, 2-bathr ...
From $238 per night (USD)Expedia
- From $355 per night (USD)
VRBO
Wintergreen Resort Getaway w/ Deck, Mountain View!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 13
Enjoy easy access to all of the excitement Wintergreen Resort has to offer at this charming Roseland vacation rental! Lo ...
From $355 per night (USD)VRBO
- From $646 per night (USD)
Expedia
The Brew Ridge Trail's Most Unique Home. Sleeps 12
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Surely you've heard about the "Almost World-Famous Boogie Nights Manor". The Boog has remained the #1 rated STR property ...
From $646 per night (USD)Expedia
- From $214 per night (USD)
VRBO
Walking Distance to Ski Slopes! Cozy Condo that sleeps 4!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Just 3-5 minutes walk to the Slopes, Ski Check in, the Market, Restaurants, Shops and Entertainment, our newly renovated ...
From $214 per night (USD)VRBO
- From $1378 per night (USD)
Expedia
Heaven On Earth ~ Wintergreen Mountain
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 16
Nestled amid the pristine beauty of the towering mountains, Heaven On Earth provides the perfect alpine escape for those ...
From $1378 per night (USD)Expedia
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VRBO
Wintergreen Oasis - PRIVATE POOL & SAUNA
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 16
This Wintergreen Oasis is a private home nestled in the Stoney Creek area of Wintergreen Resort. This 1.3 acre property ...
Click For PricingVRBO
- Click For Pricing
Expedia
The Wintergreen Treehouse
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Relax and enjoy your time secluded in nature on roughly four acres of land right down the road from Paul's Creek, many h ...
Click For PricingExpedia
- From $654 per night (USD)
VRBO
Hot Tub & Views | Mid Century Modern Wonder
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 15
Welcome to this beautiful, mid-century modern mountain home! You will fall in love with the open floor plan, chef’s kitc ...
From $654 per night (USD)VRBO
- From $1474 per night (USD)
Expedia
Dream Big in the Blue Ridge Mountains
- Bedrooms:
- 8
- Bathrooms:
- 10
- Sleeps:
- 25
Bring everybody together in our Blue Ridge Mountain 10,000 square foot home. The home is located in Nellysford`s Stoney ...
From $1474 per night (USD)Expedia
- From $302 per night (USD)
VRBO
The Blue Llama | Pets OK | Llama Loft | Fire Pit | Fenced Yard | Off Nelson 151
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to our blue-tiful Blue Llama vacation rental located at the heart of Nelson County in Nellysford, Virginia. Insp ...
From $302 per night (USD)VRBO
- From $792 per night (USD)
Expedia
Little Bear: 4br/ 4ba, mountain & valley view. Pet friendly!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Welcome to Little Bear! We'd love to provide you with a comfortable stay and clear views so you can enjoy the beauty of ...
From $792 per night (USD)Expedia
- From $331 per night (USD)
VRBO
Premiere Two bedroom getaway Slope Side Wintergreen Resort Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled in the heart of Wintergreen, This charming slope side 2-bedroom/ 2-bath. (sleeps six) condo steps from the ski ...
From $331 per night (USD)VRBO
- From $487 per night (USD)
Expedia
Cozy Wintergreen Ski Chalet -hot tub-Walk to slopes & family friendly!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to "The Brown Bear Lodge", your year-round retreat in the heart of Wintergreen Ski Resort- just a short walk fro ...
From $487 per night (USD)Expedia
- From $297 per night (USD)
VRBO
Mountain Inn Lodge 54 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mountain Inn Pet-Friendly Loft Retreat Escape to the mountains in this cozy loft-style guest room at the Mountain Inn, ...
From $297 per night (USD)VRBO
- From $206 per night (USD)
VRBO
- NEW - Spruce Creek Retreat
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Relax with the whole family at this peaceful cottage nestled in the heart of the blue ridge mountains. Short distance to ...
From $206 per night (USD)VRBO
- From $438 per night (USD)
VRBO
Hot Tub Pool Table Dog OK Tennis Golf Shuffleboard
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
8min walk or 3min drive to ski. Sweeping views year round. Retreats, romantic weekends or adventurous getaways. Close to ...
From $438 per night (USD)VRBO
- From $194 per night (USD)
Expedia
Sleepy Bear Chalet
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Escape to the mountains and enjoy your peace and quiet from the chaos of everyday life. Relax by the fire at night and s ...
From $194 per night (USD)Expedia
- From $577 per night (USD)
VRBO
Enjoy all 4 seasons at this spacious, pet friendly home! Great views, sleeps 10
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
You won’t be able to look away from the spectacular Shenandoah Valley and Blue Ridge mountain views offered by this Wint ...
From $577 per night (USD)VRBO
- From $449 per night (USD)
Expedia
Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Welcome to the Mountain Treehouse! We recently renovated the home with all upgraded amenities, including a brand new hot ...
From $449 per night (USD)Expedia
- From $175 per night (USD)
VRBO
Where the Trail Ends
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Some trips are about doing everything. This one's about slowing down. Nestled inside Wintergreen Resort, this updated m ...
From $175 per night (USD)VRBO
- From $424 per night (USD)
Expedia
Diamond Adventure at Wintergreen Resort *FULLY UPDATED*
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Updated 2 bedroom/2 bathroom slope-side condo with amazing mountain views. Short walk around the building gets you to ou ...
From $424 per night (USD)Expedia
- From $193 per night (USD)
VRBO
Cozy Studio Overlooking 18 Hole
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
A slice of paradise overlooking the 18th hole and Devils Grill. Located across the street from the spa and Nature Found ...
From $193 per night (USD)VRBO
- From $225 per night (USD)
Expedia
Ski In & Out Mountain & Firework Views Studio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy a stylish experience at this centrally-located studio next to the Mountain Inn. Our spacious deck overlooks the s ...
From $225 per night (USD)Expedia
- From $207 per night (USD)
VRBO
BEARADISE “Glamping Paradise”
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Pictures Don't Do this Justice. Private Adorable One Bedroom Glamping along a Mountain Creek. The space Amazing views of ...
From $207 per night (USD)VRBO
- From $401 per night (USD)
Expedia
Bear Den Cottage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Cozy Cottage minutes from Lexington or minutes from The Parkway, Endless trails for hiking, hunting with Creek for fishi ...
From $401 per night (USD)Expedia




































































































