
George Washington National Forest Rentals
- From $596 per night (USD)
VRBO
Northridge 09 with Wintergreen Advantage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Northridge Spacious Mountain Getaway Make yourself at home in this spacious 3-bedroom, 3-bath condo in Northridge at Wi ...
From $596 per night (USD)VRBO
- From $507 per night (USD)
Expedia
Overlook 04 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Overlook Mountain Retreat Enjoy a peaceful mountain escape in this 2-bedroom, 2-bath condo in Overlook at Wintergreen R ...
From $507 per night (USD)Expedia
- From $297 per night (USD)
VRBO
Mountain Inn Lodge 79 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mountain Inn King Bed Loft Escape Make the most of your Wintergreen getaway in this inviting loft-style guest room at t ...
From $297 per night (USD)VRBO
- From $297 per night (USD)
Expedia
Mountain Inn Lodge 63 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mountain Inn Pet-Friendly King Loft Enjoy a relaxing mountain getaway in this inviting loft-style guest room at the Mou ...
From $297 per night (USD)Expedia
- From $744 per night (USD)
VRBO
Shenandoah Ridge 09 with Wintergreen Advantage
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Shenandoah Ridge Spacious Mountain Escape Enjoy a spacious mountain escape in this 4-bedroom, 4-bath condo at Shenandoa ...
From $744 per night (USD)VRBO
- From $297 per night (USD)
Expedia
Mountain Inn Lodge 52 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Mountain Inn Cozy Loft Retreat Enjoy a charming mountain getaway in this cozy loft-style guest room at the Mountain Inn ...
From $297 per night (USD)Expedia
- From $829 per night (USD)
VRBO
Overlook 48 with Wintergreen Advantage
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Overlook Spacious Mountain Retreat Enjoy a spacious mountain escape in this inviting 4-bedroom, 4-bath condo at Overloo ...
From $829 per night (USD)VRBO
- From $507 per night (USD)
Expedia
Cliffs 26 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Cliffs Mountain Getaway Relax and enjoy the mountain setting in this 2-bedroom, 2-bath condo in Cliffs, located in Wint ...
From $507 per night (USD)Expedia
- From $507 per night (USD)
VRBO
Overlook 05 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Overlook Cozy Mountain Escape Escape to the mountains in this 2-bedroom, 2-bath condo in Overlook at Wintergreen Resort ...
From $507 per night (USD)VRBO
- From $504 per night (USD)
Expedia
Highlands 05 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Highlands Mountain Escape Escape to the mountains in this 2-bedroom, 2-bath condo in Highlands at Wintergreen Resort, n ...
From $504 per night (USD)Expedia
- From $297 per night (USD)
VRBO
Mountain Inn Lodge 78 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mountain Inn King Bed Loft Retreat Settle into a peaceful mountain escape in this cozy loft-style guest room at the Mou ...
From $297 per night (USD)VRBO
- From $297 per night (USD)
Expedia
Mountain Inn Lodge 62 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mountain Inn Two-Double Loft Escape Plan a relaxing Wintergreen getaway in this charming loft-style guest room at the M ...
From $297 per night (USD)Expedia
- From $297 per night (USD)
VRBO
Mountain Inn Lodge 61 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mountain Inn Two-Queen Loft Retreat Make your next Wintergreen getaway comfortable and convenient in this loft-style gu ...
From $297 per night (USD)VRBO
- From $744 per night (USD)
Expedia
Trillium Place 01 with Wintergreen Advantage
- Bedrooms:
- 0
- Bathrooms:
- 4
- Sleeps:
- 8
Trillium Spacious Mountain Retreat Escape to the mountains in this spacious 4-bedroom, 3-bath condo at Trillium, locate ...
From $744 per night (USD)Expedia
- From $604 per night (USD)
VRBO
Stoneridge 69 with Wintergreen Advantage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Stoneridge Pet-Friendly Mountain Retreat Enjoy a memorable mountain getaway in this spacious 3-bedroom, 3-bath condo at ...
From $604 per night (USD)VRBO
- From $744 per night (USD)
Expedia
Shenandoah Ridge 16 with Wintergreen Advantage
- Bedrooms:
- 0
- Bathrooms:
- 4
- Sleeps:
- 8
Shenandoah Ridge Relaxing Mountain Retreat Experience a relaxing mountain getaway in this spacious 4-bedroom, 4-bath co ...
From $744 per night (USD)Expedia
- From $297 per night (USD)
VRBO
Mountain Inn Lodge 58 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mountain Inn King Bed Loft Getaway Escape to the mountains in this comfortable loft-style guest room at the Mountain In ...
From $297 per night (USD)VRBO
- From $550 per night (USD)
Expedia
Fairway Woods 36 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Fairway Woods Cozy Mountain Escape Unwind in the peaceful mountain setting of this 3-bedroom, 2-bath condo in Fairway W ...
From $550 per night (USD)Expedia
- From $870 per night (USD)
VRBO
Shenandoah Ridge 13 with Wintergreen Advantage
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Shenandoah Ridge Spacious Mountain Escape Make the most of your Wintergreen getaway in this spacious 5-bedroom, 4-bath ...
From $870 per night (USD)VRBO
- From $297 per night (USD)
Expedia
Mountain Inn Lodge 55 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mountain Inn Double-Bed Loft Retreat Enjoy a relaxing stay in this inviting loft-style guest room at the Mountain Inn, ...
From $297 per night (USD)Expedia
- From $870 per night (USD)
VRBO
Stonewall Court 21 with Wintergreen Advantage
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Stonewall Court Five-Bedroom Mountain Escape Settle into a spacious mountain retreat in this 5-bedroom, 4½-bath condo a ...
From $870 per night (USD)VRBO
- From $270 per night (USD)
Expedia
Timbers Studio 08 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Timbers King Bed Hotel-Style Escape Enjoy a comfortable mountain getaway in this inviting hotel-style guest room at the ...
From $270 per night (USD)Expedia
- From $313 per night (USD)
VRBO
Timbers Studio 05 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Timbers Pet-Friendly King Retreat Enjoy a comfortable hotel-style guest room in the Timbers complex, conveniently locat ...
From $313 per night (USD)VRBO
- From $270 per night (USD)
Expedia
Mountain Inn Studio 96 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mountain Inn Main-Floor King Getaway Settle into a welcoming hotel-style guest room on the main floor of the Mountain I ...
From $270 per night (USD)Expedia
- From $339 per night (USD)
VRBO
Laurelwood 44 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Laurelwood Mountain Escape Escape to the mountains in this 1-bedroom, 1-bath condo in Laurelwood at Wintergreen Resort, ...
From $339 per night (USD)VRBO
- From $270 per night (USD)
Expedia
Mountain Inn Studio 97 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mountain Inn Pet-Friendly King Retreat Enjoy a relaxing mountain getaway in this charming hotel-style guest room on the ...
From $270 per night (USD)Expedia
- From $313 per night (USD)
VRBO
Timbers Studio 07 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Timbers King Bed Hotel-Style Retreat Settle into a welcoming hotel-style guest room in the Timbers complex, convenientl ...
From $313 per night (USD)VRBO
- From $360 per night (USD)
Expedia
Highlands 37 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Highlands Mountain Retreat Settle into a cozy 1-bedroom, 2-bath condo in Highlands, tucked away in Wintergreen's scenic ...
From $360 per night (USD)Expedia
- From $360 per night (USD)
VRBO
Highridge Court 24 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Highridge Court Mountain Escape Enjoy a cozy retreat in this 1-bedroom, 2-bath condo in Highridge Court, nestled in Win ...
From $360 per night (USD)VRBO
- From $339 per night (USD)
Expedia
Laurelwood 84 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Laurelwood Mountain Getaway Enjoy a cozy retreat in this 1-bedroom, 1-bath condo in Laurelwood at Wintergreen Resort, i ...
From $339 per night (USD)Expedia
- From $360 per night (USD)
VRBO
Cliffs 21 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Cliffs Mountain RetreatCliffs Mountain Retreat Escape to the mountains in this 1-bedroom, 1-bath condo in Cliffs, locat ...
From $360 per night (USD)VRBO
- From $267 per night (USD)
Expedia
Timbers Studio 06 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Timbers King Bed Hotel-Style Retreat Settle into a cozy hotel-style guest room in the Timbers buildings, conveniently l ...
From $267 per night (USD)Expedia
- From $465 per night (USD)
VRBO
Three Ridges 91 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Three Ridges Cozy Mountain Retreat Make yourself at home in this 2-bedroom, 2-bath condo in the Three Ridges community ...
From $465 per night (USD)VRBO
- From $843 per night (USD)
Expedia
Nancy's Edelweiss with Wintergreen Advantage
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
This lovely 6-bedroom home is located on a quiet cul-de-sac and only minutes away from the Mountain Inn & main ski area. ...
From $843 per night (USD)Expedia
- From $747 per night (USD)
VRBO
Chestnut Springs with Wintergreen Advantage
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
This beautiful five bedroom home is conveniently located less than one mile from the Devil’s Knob Golf and Tennis Center ...
From $747 per night (USD)VRBO
- From $643 per night (USD)
Expedia
Bull City Bungalow with Wintergreen Advantage
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to our Bull City Bungalow! Bull City Bungalow is a fully renovated and tastefully decorated 4 bedroom, 3 ½ bath ...
From $643 per night (USD)Expedia
- From $510 per night (USD)
VRBO
Bear Necessities with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Start your adventure and step into Bear Necessities. A picturesque three-bedroom home in the rolling landscape of Winter ...
From $510 per night (USD)VRBO
- From $643 per night (USD)
Expedia
Blackrock Vista with Wintergreen Advantage
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
4-Bedroom Home / Sleeps 8 Home Features • 3008 Square Feet • Complete modern kitchen with full-size refrigerator, stove, ...
From $643 per night (USD)Expedia
- From $313 per night (USD)
VRBO
Timbers Studio 43 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Timbers King Bed Hotel-Style Retreat Relax in a welcoming hotel-style guest room at the Timbers complex, ideally locate ...
From $313 per night (USD)VRBO
- From $270 per night (USD)
Expedia
Timbers Studio 14 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Timbers Queen Bed Hotel-Style Retreat Make yourself comfortable in this inviting hotel-style guest room at the Timbers ...
From $270 per night (USD)Expedia
- From $642 per night (USD)
VRBO
Whispering Elm with Wintergreen Advantage
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Whispering Elm is located at the top of the mountain in close proximity to fabulous hiking, skiing, the Devil’s Knob Gol ...
From $642 per night (USD)VRBO
- From $270 per night (USD)
Expedia
Timbers Studio 18 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Timbers King Bed Hotel-Style Getaway Settle into a welcoming hotel-style guest room at the Timbers complex, ideally loc ...
From $270 per night (USD)Expedia
- From $746 per night (USD)
VRBO
Serendipity with Wintergreen Advantage
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
With only 2 steps to access entry to the house, it is easily accessible for your convenience. A beautiful, large deck is ...
From $746 per night (USD)VRBO
- From $313 per night (USD)
Expedia
Timbers Studio 13 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
"Timbers King Bed Mountain Retreat Make yourself comfortable in this inviting hotel-style guest room at the Timbers com ...
From $313 per night (USD)Expedia
- From $267 per night (USD)
VRBO
Timbers Studio 38 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Timbers Pet-Friendly King Retreat Escape to a welcoming hotel-style guest room at the Timbers complex, ideally situated ...
From $267 per night (USD)VRBO
- From $351 per night (USD)
Expedia
Secluded 20+ Acre Retreat Near Brew & Wine Trails
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Your Nelson County Retreat Escape to our charming and family-friendly home set on over 20 private, quiet and ...
From $351 per night (USD)Expedia
- From $211 per night (USD)
VRBO
New Blue RIdge Mountains Montebello, Virginia with stary stary skies
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
idyllic setting by North Fork of Tye River. Sit on deck or by fire pit. Free wood provided. 100 acre parcel that you ...
From $211 per night (USD)VRBO
- From $787 per night (USD)
Expedia
Mountain Mindset: Pup Friendly + Trail
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Downstairs Living Room: Smart TV, 2 couches, accent chairs (comfortable seating for 7-8). Sitting Room: 4 lounge chair ...
From $787 per night (USD)Expedia
- From $227 per night (USD)
VRBO
Wintergreen Mountain Views - Diamond in the Slopes - Close to Breweries & Hiking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Soak in the spectacular views of the Blue Ridge Mountains from the top of Wintergreen Resort. High ceilings and open lay ...
From $227 per night (USD)VRBO
- From $381 per night (USD)
Expedia
Charming cozy RIVERFRONT cottage on the Piney River. A little slice of heaven!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Chestnut House The perfect place for you and your family to rest, unplug, enjoy novice trout fishing, and stargaze ...
From $381 per night (USD)Expedia
- From $390 per night (USD)
VRBO
Romantic or Family Vacay w/ Stunning Mtn Views & Hot Tub near Crabtree Falls
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Enjoy a romantic getaway or relax with the whole family on a special family vacation at this peaceful retreat in the mou ...
From $390 per night (USD)VRBO
- From $457 per night (USD)
Expedia
Amazing Views / Hot Tub / 15 mins to Wineries / 3200 sq ft
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to Adrian's Den: a mountaintop hideaway perfect for groups, family reunions, and wedding parties. ★3,200 sq ft ...
From $457 per night (USD)Expedia
- From $227 per night (USD)
VRBO
Mountain View Meadow Cottage - Blue Ridge Mountains and Virginia wine country
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Cottage in the heart of the Blue Ridge Mountains and Virginia wine country. Kick back and relax in this calm and stylis ...
From $227 per night (USD)VRBO
- From $604 per night (USD)
Expedia
Gum Tree 5 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Spacious Three-Bedroom Mountain Escape Enjoy a spacious mountain getaway in this apartment-style condominium, featuring ...
From $604 per night (USD)Expedia
- From $312 per night (USD)
VRBO
\"Fall\" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to The Retreat at Three Ridges! Our cozy, Scandinavian-inspired condo is your perfect Blue Ridge Mountain getawa ...
From $312 per night (USD)VRBO
- From $328 per night (USD)
Expedia
Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy a cozy mountain getaway at this 2BR, 2BA Wintergreen condo, ideally located for ski season and year-round resort a ...
From $328 per night (USD)Expedia
- From $737 per night (USD)
VRBO
Art & Soul: Sauna/Hot Tub & EV Charger/Hammocks
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Living Room: Spacious and inviting with large windows, cozy seating area with a fireplace, coffee table and bookshelf fi ...
From $737 per night (USD)VRBO
- From $554 per night (USD)
Expedia
Ridge Retreat @ Wintergreen!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Top of the Mountain! Enjoy a view of the slopes and a backdrop view of many miles beyond that. You will want to wake up ...
From $554 per night (USD)Expedia
- From $513 per night (USD)
VRBO
Blue Rivers Cottage and Loft
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
The accommodation features a spacious and inviting 3-bedroom, 2-bathroom home with an open floor plan that seamlessly co ...
From $513 per night (USD)VRBO
- From $353 per night (USD)
Expedia
Sycamore Shade: 151 House, HOT TUB, Mountain Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sycamore Shade is a one-level home with comfortable private rooms and engaging community spaces. The house is accessible ...
From $353 per night (USD)Expedia
- From $353 per night (USD)
VRBO
Blue Rivers Cottage with Mountain Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
One level living space. Spacious, open floor plan with a sitting room, open kitchen/dining room and family room with TV. ...
From $353 per night (USD)VRBO
- From $166 per night (USD)
Expedia
Blue Rivers Loft on the Brew Ridge Trail
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Located near the famous Route 151, the area is surrounded by popular breweries and vineyards, offering plenty of options ...
From $166 per night (USD)Expedia
- From $864 per night (USD)
VRBO
Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to Altitude Adjustment!! The whole group will love this spacious and unique space. In the heart of the "Brew R ...
From $864 per night (USD)VRBO
- From $667 per night (USD)
Expedia
Afton Awaits: Pool, Mountain View
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Living Room: Spacious and inviting with cozy seating area with a fireplace, coffee table two couches and a smart TV. Di ...
From $667 per night (USD)Expedia
- From $260 per night (USD)
VRBO
Serene haven \"The Nest\" in Wintergreen, close to activities and restaurants.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
A warm space to relax and recharge. Close to it all or simply do nothing. Near hiking, golf, the slopes, tennis, spa and ...
From $260 per night (USD)VRBO
- From $344 per night (USD)
Expedia
Mountain View Vista: Resort Condo w/ Views
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
The condo's main features are as described: KITCHEN: Newly renovated and fully stocked with a fridge, dishwasher, oven ...
From $344 per night (USD)Expedia
- From $821 per night (USD)
VRBO
6-bedroom house in Nellysford with WiFi AC Skiing Tubing and Golf
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 14
Discover the beauty of Nellysford from this 6-bedroom house. Marvelous king and queen beds await you, ensuring a brillia ...
From $821 per night (USD)VRBO
- From $359 per night (USD)
Expedia
Mid‑Century Retreat • Near Breweries • Sleeps 12
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Stay minutes from Wintergreen and come home to a place built for group fun — hot tub evenings, a game room for the kids, ...
From $359 per night (USD)Expedia
- From $925 per night (USD)
VRBO
Red White & WTG: Hot Tub, 5 Bedrooms!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 16
Welcome to Red, White and Wintergreen! Escape to the scenic beauty of Wintergreen Resort in Virginia with this spacious ...
From $925 per night (USD)VRBO
- From $465 per night (USD)
Expedia
Laurelwood 95 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Laurelwood Easy-Access Mountain Retreat Enjoy a relaxing mountain escape in this comfortable 2-bedroom, 2-bath retreat ...
From $465 per night (USD)Expedia
- From $313 per night (USD)
VRBO
Diamond Hill Studio 09 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Diamond Hill Pet-Friendly King Retreat Escape to a cozy mountain getaway in this hotel-style guest room at the Diamond ...
From $313 per night (USD)VRBO
- From $270 per night (USD)
Expedia
Timbers Studio 44 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Timbers King Bed Hotel-Style Retreat Settle into a comfortable hotel-style guest room at the Timbers complex, convenien ...
From $270 per night (USD)Expedia
- From $270 per night (USD)
VRBO
Mountain Inn Studio 91 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mountain Inn Main-Floor King Retreat Enjoy a comfortable mountain getaway in this charming hotel-style guest room at th ...
From $270 per night (USD)VRBO
- From $313 per night (USD)
Expedia
Timbers Studio 15 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Timbers King Bed Mountain Retreat Make yourself comfortable in this inviting hotel-style guest room at the Timbers comp ...
From $313 per night (USD)Expedia
- From $313 per night (USD)
VRBO
Timbers Studio 45 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Timbers King Bed Mountain Escape Enjoy a comfortable hotel-style guest room at the Timbers complex, conveniently positi ...
From $313 per night (USD)VRBO
- From $504 per night (USD)
Expedia
The Osprey with Wintergreen Advantage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Come enjoy the freedom and tranquility of The Osprey perched among the trees and rock out cropping of Wintergreen Mounta ...
From $504 per night (USD)Expedia
- From $465 per night (USD)
VRBO
Laurelwood 24 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Laurelwood Cozy Mountain Escape Enjoy a comfortable mountain getaway in Laurelwood at Wintergreen Resort, ideally locat ...
From $465 per night (USD)VRBO
- From $313 per night (USD)
Expedia
Timbers Studio 47 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Timbers King Bed Hotel-Style Getaway Settle into a cozy hotel-style guest room at the Timbers complex, ideally situated ...
From $313 per night (USD)Expedia
- From $503 per night (USD)
VRBO
Cabin Blue Ridge with Wintergreen Advantage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This new, modern three-bedroom home is tucked away in a quiet location of the resort property, yet has easy, quick acces ...
From $503 per night (USD)VRBO
- From $340 per night (USD)
Expedia
Timbers Lodge 39 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
First floor slope side unit with walkout ski in and ski out access. Located in the Timbers complex near the Blackrock Vi ...
From $340 per night (USD)Expedia
- From $354 per night (USD)
VRBO
Timbers Lodge 23 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Timbers Pet-Friendly King Loft Bring your pup along for a memorable mountain getaway in this cozy loft-style guest room ...
From $354 per night (USD)VRBO
- From $297 per night (USD)
Expedia
Timbers Lodge 56 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Timbers Queen Bed Loft Retreat Settle into a comfortable mountain getaway in this inviting loft-style guest room at the ...
From $297 per night (USD)Expedia
- From $297 per night (USD)
VRBO
Timbers Lodge 54 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Timbers King Bed Loft Escape Discover a comfortable mountain retreat in this loft-style guest room at the Timbers compl ...
From $297 per night (USD)VRBO
- From $294 per night (USD)
Expedia
Timbers Lodge 58 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Timbers King Bed Loft Getaway Make the most of your Wintergreen vacation in this welcoming loft-style guest room at the ...
From $294 per night (USD)Expedia
- From $423 per night (USD)
VRBO
Charming Farmhouse across from Devils Backbone Brewery.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Beech Grove Farmhouse is an early century farmhouse situated in the foothills of the Blue Ridge mountains, has a spr ...
From $423 per night (USD)VRBO
- From $270 per night (USD)
Expedia
Timbers Studio 46 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Timbers King Bed Hotel-Style Getaway Relax in a cozy hotel-style guest room at the Timbers complex, ideally located nea ...
From $270 per night (USD)Expedia
- From $2547 per night (USD)
VRBO
Blue Ridge Retreat with Wintergreen Advantage
- Bedrooms:
- 10
- Bathrooms:
- 10
- Sleeps:
- 20
This majestic ten-bedroom, four level home offers all the comforts of a mountain lodge. Named the “Blue Ridge Retreat”, ...
From $2547 per night (USD)VRBO
- From $844 per night (USD)
Expedia
Wooded Mtn. Retreat with Wintergreen Advantage
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Wooded Mountain Retreat Wooded Mountain Retreat is nestled in a quiet wooded setting across from the Appalachian Trail a ...
From $844 per night (USD)Expedia
- From $270 per night (USD)
VRBO
Mountain Inn Studio 94 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mountain Inn Main-Floor King Escape Relax in a charming hotel-style guest room on the main floor of the Mountain Inn, i ...
From $270 per night (USD)VRBO
- From $340 per night (USD)
Expedia
Timbers Lodge 49 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Timbers King Bed Loft Escape Relax in a welcoming loft-style guest room at the Timbers complex, conveniently located ne ...
From $340 per night (USD)Expedia
- From $270 per night (USD)
VRBO
Timbers Studio 16 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Timbers Pet-Friendly King Retreat Unwind in a cozy hotel-style guest room at the Timbers complex, conveniently located ...
From $270 per night (USD)VRBO
- From $270 per night (USD)
Expedia
Mountain Inn Studio 95 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mountain Inn Main-Floor King Retreat Make yourself at home in this inviting hotel-style guest room on the main floor of ...
From $270 per night (USD)Expedia
- From $504 per night (USD)
VRBO
Above The Clouds with Wintergreen Advantage
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Experience a stunning mountain retreat and connect with nature at Above The Clouds on Devils Knob Loop. Breathtaking vie ...
From $504 per night (USD)VRBO
- From $297 per night (USD)
Expedia
Timbers Lodge 50 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Timbers King Bed Loft Retreat Make yourself comfortable in this inviting loft-style guest room at the Timbers complex, ...
From $297 per night (USD)Expedia
- From $340 per night (USD)
VRBO
Timbers Lodge 53 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Timbers King Bed Loft Retreat Make yourself at home in this charming loft-style guest room at the Timbers complex, idea ...
From $340 per night (USD)VRBO
- From $2612 per night (USD)
Expedia
Mountaintop Lodge with Wintergreen Advantage
- Bedrooms:
- 9
- Bathrooms:
- 9
- Sleeps:
- 18
One of Wintergreen’s premier mountain lodges (near the top of the mountain), this beautifully appointed 9 bedroom & 9.5 ...
From $2612 per night (USD)Expedia
- From $336 per night (USD)
VRBO
Timbers Lodge 57 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Timbers Pet-Friendly King Loft Retreat Bring your pup along for a relaxing Wintergreen getaway in this inviting loft-st ...
From $336 per night (USD)VRBO
- From $297 per night (USD)
Expedia
Mountain Inn Studio 53 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Mountain Inn King & Full Mountain Retreat Settle into a comfortable mountain escape at the Mountain Inn, conveniently s ...
From $297 per night (USD)Expedia
- From $465 per night (USD)
VRBO
Fairway Woods 44 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Fairways Woods Mountain Escape Relax and recharge in this 2-bedroom, 2-bath condo in Fairways Woods, located in Winterg ...
From $465 per night (USD)VRBO
- From $667 per night (USD)
Expedia
Highlands 42 with Wintergreen Advantage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Highlands Relaxing Mountain Retreat Relax and recharge in this inviting 3-bedroom, 3-bath condo in Highlands at Winterg ...
From $667 per night (USD)Expedia




































































































