
George Washington National Forest Rentals
- From $379 per night (USD)
VRBO
Wintergreen Mountain Escape-Ski, Hike & Unwind-4 private bedrooms
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Your Family's Blue Ridge Escape Awaits.. There's a moment that happens on our front deck, almost every morning of every ...
From $379 per night (USD)VRBO
- From $629 per night (USD)
Expedia
Mtn & Lake Views: Serene Wintergreen Resort Escape
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Escape to this newly renovated 4-bedroom, 2-bath vacation rental, nestled within Wintergreen’s Stoney Creek area. Admire ...
From $629 per night (USD)Expedia
- From $297 per night (USD)
VRBO
Mountain Inn Lodge 80 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mountain Inn King Bed Loft Retreat Settle into a comfortable mountain hideaway at the Mountain Inn in this charming lof ...
From $297 per night (USD)VRBO
- From $309 per night (USD)
Expedia
Bluebird Cottage: Near 151 + Appalachian Trail
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
KITCHEN - fully stocked kitchen with all major appliances LIVING ROOM - formal living room with ample seating and boar ...
From $309 per night (USD)Expedia
- From $572 per night (USD)
VRBO
Family Retreat - Hot Tub, Games, Fireplace, Pet Friendly, Firepits & Grill
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 14
Bring the whole family to this warm mountain home! Welcome to Whitetail Lodge, a well designed home in the heart of Wint ...
From $572 per night (USD)VRBO
- From $861 per night (USD)
Expedia
Mountain Escape: Golf, Hiking, Hot Tub & Scenic Views at 5BR Wintergreen Home
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
The Hot Tub Time Machine is a beautiful 5 bedroom, 4 bathroom home that sleeps 12 located in the Blue Ridge Mountains of ...
From $861 per night (USD)Expedia
- From $488 per night (USD)
VRBO
Wintergreen Resort - Mountain home w/4-bedroom 3 bath, Hot Tub & Wifi
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Fantastic Mountain Views & Close to the Resort hub. Bright and open Wintergreen 4 bedroom 3 full bath home perfectly sit ...
From $488 per night (USD)VRBO
- From $576 per night (USD)
Expedia
Luxury Oasis w/outdoor lounge! Hiking, lakes, brew trails & golf. Pet friendly!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
"One of the best Airbnb's I have rented! House was beautiful and pictures don't do justice!" Candice Welcome to Sundown ...
From $576 per night (USD)Expedia
- From $850 per night (USD)
VRBO
Luxurious 5-bedroom house off Nelson 151 in Nellysford
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to High View Haven! HVH offers a relaxing space while skiing at Wintergreen, golfing at Stoney Creek, or sampl ...
From $850 per night (USD)VRBO
- From $532 per night (USD)
Expedia
Cozy 6-bedroom cabin in Wintergreen Resort
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 14
This charming mountain house spans three floors, providing ample space for large families or multiple families to enjoy ...
From $532 per night (USD)Expedia
- From $497 per night (USD)
VRBO
Cheerful 3-Bedroom Cabin in amazing Wintergreen Resort
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Rustic 3 bedroom mountain home. Come and relax in Wintergreen! This home has the everything you are looking for when you ...
From $497 per night (USD)VRBO
- From $332 per night (USD)
VRBO
Welcome to the newly appointed Everett Estate: Where Modern Luxury Meets Historic Charm
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to the newly appointed Everett Estate: Where Modern Luxury Meets Historic Charm. Boasting picturesque mountain v ...
From $332 per night (USD)VRBO
- From $332 per night (USD)
VRBO
Welcome to the newly appointed Everett Estate: Where Modern Luxury Meets Historic Charm
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to the newly appointed Everett Estate: Where Modern Luxury Meets Historic Charm. Boasting picturesque mountain v ...
From $332 per night (USD)VRBO
- From $332 per night (USD)
VRBO
Welcome to the newly appointed Everett Estate: Where Modern Luxury Meets Historic Charm
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to the newly appointed Everett Estate: Where Modern Luxury Meets Historic Charm. Boasting picturesque mountain v ...
From $332 per night (USD)VRBO
- From $465 per night (USD)
VRBO
Welcome to the newly appointed Everett Estate: Where Modern Luxury Meets Historic Charm
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to the newly appointed Everett Estate: Where Modern Luxury Meets Historic Charm. Boasting picturesque mountain v ...
From $465 per night (USD)VRBO
- From $332 per night (USD)
VRBO
Everett Estate | Suite 1
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to the newly appointed Everett Estate: Where Modern Luxury Meets Historic Charm. Boasting picturesque mountain v ...
From $332 per night (USD)VRBO
- From $316 per night (USD)
VRBO
Luxury Condo in the Sky! Finest in Wintergreen!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to our recently renovated luxury condo in the sky! Perched on the edge of the Wintergreen ridgeline, we are just ...
From $316 per night (USD)VRBO
- From $204 per night (USD)
Expedia
Wintergreen Resort Condo: Deck & Golf Course Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
On-Site Golf & Ski Storage | Covered Deck | Near Hiking Embark on a nature escape worth remembering at this 2-bedroom, ...
From $204 per night (USD)Expedia
- From $297 per night (USD)
VRBO
Mountain Inn Lodge 86 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mountain Inn King Bed Loft Retreat Make your Wintergreen getaway memorable in this inviting loft-style guest room at th ...
From $297 per night (USD)VRBO
- From $267 per night (USD)
Expedia
Mountain Inn Studio 92 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mountain Inn Main-Floor King Getaway Settle into a stylish hotel-style guest room on the main floor of the Mountain Inn ...
From $267 per night (USD)Expedia
- From $360 per night (USD)
VRBO
Highlands 02 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Cozy Highlands Mountain Escape Unwind in this 1-bedroom, 1-bath condo in Highlands, nestled in Wintergreen's scenic Dev ...
From $360 per night (USD)VRBO
- From $297 per night (USD)
Expedia
Mountain Inn Lodge 57 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mountain Inn King Bed Loft Escape Make yourself at home in this inviting loft-style guest room at the Mountain Inn, con ...
From $297 per night (USD)Expedia
- From $294 per night (USD)
VRBO
Mountain Inn Lodge 85 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mountain Inn King Bed Loft Getaway Take a break in the mountains with a stay in this inviting loft-style guest room at ...
From $294 per night (USD)VRBO
- From $297 per night (USD)
Expedia
Mountain Inn Lodge 66 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mountain Inn Two-Double Loft Retreat Enjoy the convenience of a mountain getaway in this inviting loft-style guest room ...
From $297 per night (USD)Expedia
- From $227 per night (USD)
VRBO
Theater Room, Fooseball, Firepit, Mountains!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to Alpine Adventure, a spacious and luxurious Virginia mountain vacation rental located in the heart of Wintergr ...
From $227 per night (USD)VRBO
- From $1142 per night (USD)
Expedia
Designer Home w/ Incredible Views, Sleeps 16
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 16
Welcome to Highlands Overlook, a designer-decorated home in the heart of Wintergreen. The deck is second-to-none, comple ...
From $1142 per night (USD)Expedia
- From $731 per night (USD)
VRBO
Eagles Court 24 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Eagles Court Classic Mountain Retreat Enjoy a classic Wintergreen mountain getaway in this inviting 3-bedroom, 2-bath c ...
From $731 per night (USD)VRBO
- From $228 per night (USD)
Expedia
5 minutes to Blue Ridge Parkway, Crabtree Falls, hiking, wineries, breweries
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
New cabin two miles off Blue Ridge Parkway, Appalachian Trail. Near Crabtree Falls, wineries, breweries, distilleries, ...
From $228 per night (USD)Expedia
- From $699 per night (USD)
VRBO
Prime Location! Ski In, Ski Out 3BDR plus bonus room, 3BA, Condo on Dobie
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Cozy, well appointed, 2 floor condo, located steps from the top of the Dobie lift. Vaulted ceiling gives spacious feel! ...
From $699 per night (USD)VRBO
- From $559 per night (USD)
Expedia
Modern Nellysford Getaway w/ View: Deck & Fire Pit
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Elevate your mountain getaway at this newly built vacation rental in Nellysford! From the beautiful outdoor space with a ...
From $559 per night (USD)Expedia
- From $293 per night (USD)
VRBO
Wintergreen Resort: Weeping Rock Retreat
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Weeping Rock Retreat in Wintergreen Resort on. This 4 bedroom, 3 full bath home is certain to fit your indiv ...
From $293 per night (USD)VRBO
- From $507 per night (USD)
Expedia
Highridge Court 08 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Highridge Court Easy-Access Retreat Enjoy a comfortable mountain getaway in this 2-bedroom, 2-bath condo in Highridge C ...
From $507 per night (USD)Expedia
- From $844 per night (USD)
VRBO
Memory Maker with Wintergreen Advantage
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Memory Maker sits right on the 1st hole of Devils Knob Golf course, right across from the tennis and pickle ball courts, ...
From $844 per night (USD)VRBO
- From $465 per night (USD)
Expedia
Stoneridge 41 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Stoneridge Cozy Mountain Retreat Escape to the mountains in this 2-bedroom, 2-bath condo in Stoneridge, nestled in Wint ...
From $465 per night (USD)Expedia
- From $504 per night (USD)
VRBO
Nowhere Land with Wintergreen Advantage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Nowhere Land, a cozy getaway perfect for 2 families (up to 8 guests).This spacious retreat is located near Up ...
From $504 per night (USD)VRBO
- From $744 per night (USD)
Expedia
Shenandoah Ridge 11 with Wintergreen Advantage
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Shenandoah Ridge Mountain Retreat Escape to the mountains in this spacious 4-bedroom, 4½-bath condo at Shenandoah Ridge ...
From $744 per night (USD)Expedia
- From $596 per night (USD)
VRBO
Gum Tree 2 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Spacious Three-Bedroom Mountain Retreat Enjoy the comfort and space of this apartment-style condominium, featuring thre ...
From $596 per night (USD)VRBO
- From $297 per night (USD)
Expedia
Timbers Lodge 42 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Timbers King Bed Loft Getaway Settle into a charming mountain retreat in this loft-style guest room at the Timbers comp ...
From $297 per night (USD)Expedia
- From $465 per night (USD)
VRBO
Fairway Woods 49 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Fairways Woods Cozy Retreat Enjoy a peaceful mountain escape in this 2-bedroom, 2-bath condo in Fairways Woods, nestled ...
From $465 per night (USD)VRBO
- From $744 per night (USD)
Expedia
Gum Tree 4 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Blackrock Spacious Four-Bedroom Retreat Enjoy the extra space of this spacious 4-bedroom, 2-bath apartment-style condo ...
From $744 per night (USD)Expedia
- From $451 per night (USD)
VRBO
Gum Tree 3 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Comfortable Two-Bedroom Mountain Condo Enjoy a spacious 2-bedroom, 2-bath condo at Wintergreen Resort, with multiple lo ...
From $451 per night (USD)VRBO
- From $317 per night (USD)
VRBO
Buck's Cabin: Cozy retreat with hot tub. Pet- & kid-friendly!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Bring the whole family or your friends to this cozy cabin with lots of room for fun and relaxation. Check out the local ...
From $317 per night (USD)VRBO
- From $267 per night (USD)
VRBO
Timbers Studio 48 With Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Timbers King Bed Mountain Retreat Make yourself at home in this inviting hotel-style guest room at the Timbers complex, ...
From $267 per night (USD)VRBO
- From $738 per night (USD)
Expedia
NEW Warren’s Woods! Lovely 5BD, 3BA Wintergreen home. Hot Tub! NEW SPRING RATES!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Wintergreen Resort is waiting for you at this 5-bedroom house. Each room offers an unique sleeping experience, from a ki ...
From $738 per night (USD)Expedia
- From $440 per night (USD)
VRBO
Brand new 3-bedroom house at the base of the Blue Ridge Mountains
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Bucolic and chic— Take in all Nelson County’s Rockfish River Valley and “Brew Ridge Trail” (Rt. 151) have to offer in th ...
From $440 per night (USD)VRBO
- From $731 per night (USD)
Expedia
Dobie 36 with Wintergreen Advantage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Dobie Cozy Mountain Escape Enjoy a memorable mountain getaway in this inviting 3-bedroom, 3-bath condo at Dobie, conven ...
From $731 per night (USD)Expedia
- From $731 per night (USD)
VRBO
Dobie 48 with Wintergreen Advantage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Dobie Spacious Mountain Retreat Escape to Wintergreen in this spacious 3-bedroom, 3-bath condo at Dobie, ideally locate ...
From $731 per night (USD)VRBO
- From $297 per night (USD)
Expedia
Mountain Inn Lodge 77 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mountain Inn King Bed Loft Retreat Make your Wintergreen stay comfortable and convenient in this cozy loft-style guest ...
From $297 per night (USD)Expedia
- From $367 per night (USD)
VRBO
Couple's Getaway in Stoney Creek at Wintergreen!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Private Location | Ideal Area for Hikers | Wraparound Deck | 15 Mi to Wintergreen Resort A romantic retreat awaits at t ...
From $367 per night (USD)VRBO
- Click For Pricing
VRBO
Original 1798 Antique Appalachian Chestnut log cabin- \"Annies Cabin\"
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
This adorable antique Appalachian log cabin was built by Thomas Jeffersons nephew, Peter Carr in 1798 and is made comple ...
Click For PricingVRBO
- From $256 per night (USD)
VRBO
Cozy dog- friendly condo that sleeps 6 -with pools and VIEWS, minutes to slopes
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to a tranquil 2-bedroom condo at Wintergreen Resort! This well appointed property offers a perfect place for unw ...
From $256 per night (USD)VRBO
- From $1308 per night (USD)
VRBO
Oh Deer NEW LUXURY-renovated, hot tub/sauna, views
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 18
OH DEER! Welcome to your perfect escape in the Blue Ridge Mountains! Nestled just steps from the slopes of Wintergreen ...
From $1308 per night (USD)VRBO
- From $336 per night (USD)
VRBO
Timbers Lodge 31 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 $336 per night (USD)VRBO
- From $574 per night (USD)
VRBO
Foxwood at Stoney Creek • Wintergreen + Wine Trail Base • Mtn Views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Spacious 4BR/3BA home in Stoney Creek at Wintergreen on 1.4 peaceful acres. Enjoy a screened-in porch with skylights and ...
From $574 per night (USD)VRBO
- From $646 per night (USD)
VRBO
The Snow House New Hot Tub Pet Friendly Creek PacMan
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 13
Hot Tub Coming Dec. 2025*** We added a beautiful 8 seater hot tub for our deck overlooking the serene deck and creek be ...
From $646 per night (USD)VRBO
- From $378 per night (USD)
Expedia
Blue Ridge Mountain Views - Heart of VA Wine Country
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
A brand new modern farmhouse with Blue Ridge Mountain and meadow views. Enjoy the 2+ story great room with windows and ...
From $378 per night (USD)Expedia
- From $311 per night (USD)
VRBO
Recently updated - breathtaking view of the Blue Ridge Mountains
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Little Bear Lookout. Come for the view, experience the location, & enjoy the comfort! Updated in May 2022! ...
From $311 per night (USD)VRBO
- From $543 per night (USD)
VRBO
Take a break at this peaceful oasis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Take a break at this peaceful oasis. With 3 bedrooms and 2 baths in the guest house, this guest house makes an excellent ...
From $543 per night (USD)VRBO
- From $1694 per night (USD)
VRBO
Hosts groups up to 13; relax with the whole crew at this private, peaceful getaway
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 13
Hosts groups up to 13; relax with the whole crew at this private, peaceful getaway. You are just a short drive from some ...
From $1694 per night (USD)VRBO
- From $809 per night (USD)
Expedia
Everley Whole Property
- Bedrooms:
- 6
- Bathrooms:
- 8
- Sleeps:
- 20
Hosts groups up to 20! Relax with the whole crew at this private, peaceful getaway. You are just a short drive from some ...
From $809 per night (USD)Expedia
- From $307 per night (USD)
VRBO
Cozy chalet on Wintergreen Mountain
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
On a private, wooded lot, this chalet home is perfectly located in the year-round Wintergreen Resort. We’re less than a ...
From $307 per night (USD)VRBO
- From $533 per night (USD)
VRBO
Calm Creek Retreat - minutes from slopes, hot tub, large cozy family room!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
After a day on the slopes, return to Calm Creek Retreat for a relaxing hot tub soak and cozy night in by the fire! Step ...
From $533 per night (USD)VRBO
- From $850 per night (USD)
VRBO
Mountain Season Lodge
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 16
Winter, Spring, Summer, or Fall, it's ALWAYS Mountain Season! This 6 bedroom/4 bathroom house is the perfect mountain g ...
From $850 per night (USD)VRBO
- From $267 per night (USD)
Expedia
Wintergreen Condo -Steps to Ski and restaurants
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Discover the perfect blend of comfort and adventure at our Wintergreen Resort condo. Nestled amidst the pristine beauty ...
From $267 per night (USD)Expedia
- From $1820 per night (USD)
VRBO
Welcome to the newly appointed Everett Estate: Where Modern Luxury Meets Historic Charm
- Bedrooms:
- 12
- Bathrooms:
- 11
- Sleeps:
- 30
Welcome to the newly appointed Everett Estate: Where Modern Luxury Meets Historic Charm. Boasting picturesque mountain v ...
From $1820 per night (USD)VRBO
- From $359 per night (USD)
VRBO
Welcome to the newly appointed Everett Estate: Where Modern Luxury Meets Historic Charm
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to the newly appointed Everett Estate: Where Modern Luxury Meets Historic Charm. Boasting picturesque mountain v ...
From $359 per night (USD)VRBO
- From $359 per night (USD)
VRBO
Welcome to the newly appointed Everett Estate: Where Modern Luxury Meets Historic Charm
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to the newly appointed Everett Estate: Where Modern Luxury Meets Historic Charm. Boasting picturesque mountain v ...
From $359 per night (USD)VRBO
- From $359 per night (USD)
VRBO
Welcome to the newly appointed Everett Estate: Where Modern Luxury Meets Historic Charm
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to the newly appointed Everett Estate: Where Modern Luxury Meets Historic Charm. Boasting picturesque mountain v ...
From $359 per night (USD)VRBO
- From $359 per night (USD)
VRBO
Welcome to the newly appointed Everett Estate: Where Modern Luxury Meets Historic Charm
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to the newly appointed Everett Estate: Where Modern Luxury Meets Historic Charm. Boasting picturesque mountain v ...
From $359 per night (USD)VRBO
- From $340 per night (USD)
Expedia
Hot Tub EV Charger Pool Dog OK Grill Tennis Hiking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
2min drive to Wintergreen skiing. Modern-meets-mountain vibe in this 4-season chalet nestled in the treetops. Hot tub, ...
From $340 per night (USD)Expedia
- From $290 per night (USD)
VRBO
Mountain Retreat in Wintergreen!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Discover the perfect blend of comfort and convenience at this 1-bedroom condo in Wintergreen Resort. Nestled o ...
From $290 per night (USD)VRBO
- From $334 per night (USD)
Expedia
RELAX - HOT TUB & GORGEOUS MOUNTAIN VIEWS
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Need a quiet get-away? You've got the it!!! Relax on the front porch and drink in the gorgeous mountain view and lovely ...
From $334 per night (USD)Expedia
- From $469 per night (USD)
VRBO
Upscale and Family-Friendly in Wintergreen
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 16
Welcome to Sutton's Roost, a designer-decorated home in the heart of Wintergreen. A perfect spot for groups or families, ...
From $469 per night (USD)VRBO
- Click For Pricing
Expedia
Fox'em Falls
- Bedrooms:
- 0
- Bathrooms:
- 0
- Sleeps:
- 0
About this space Fox'em Falls is ready to host your group with 3 bedrooms, 2 full baths, a kitchen, dining area, cozy fa ...
Click For PricingExpedia
- From $287 per night (USD)
VRBO
Birds Eye: Mntn Views K-Bed DogOK Pool Tennis Golf
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Spend your days hiking the area’s 30+ miles of trails, completing the ninja warrior course, soaring down a zip line at ~ ...
From $287 per night (USD)VRBO
- From $622 per night (USD)
Expedia
The Bear's Den at Wintergreen- 6 Bedroom
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 15
Welcome to the Bear's Den, a comfortable three story home in Wintergreen Resort for family and friends to make mountain ...
From $622 per night (USD)Expedia
- From $348 per night (USD)
VRBO
Bide-a-Wee- Hike the Trails! Close to the slopes!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Bide-a-Wee! This cozy mid-century modern mountain home has 3 bedrooms and 2 baths within a 10-minutes walking ...
From $348 per night (USD)VRBO
- From $698 per night (USD)
Expedia
Game Room, Screen Porch, Family-Friendly, Hot Tub near 151 Brew Trail and hiking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Gather family and friends for a memorable getaway at The Myrtle at Wintergreen. This spacious golf-course retreat combin ...
From $698 per night (USD)Expedia
- From $353 per night (USD)
VRBO
Whispering Creek Hot Tub Pool TennisGolf King Beds
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
4min to Ski. Nestled next to a perennial mountain stream in Wintergreen Resport this cozy 3 bedroom, 2.5 bath house with ...
From $353 per night (USD)VRBO
- From $487 per night (USD)
Expedia
Clean family-friendly 5BR in the HEART of Virginia's Wine Country
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 13
Come to Sunnyside! A new 5 bedroom home with game room, hot tub, and space for 12 people on 4 acres on a private farm ro ...
From $487 per night (USD)Expedia
- From $513 per night (USD)
VRBO
Beautiful Mountain Condo…Steps to Resort/hiking/restaurants
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 0
Our Pet Friendly condo is situated right on Eagle Swoop. Step out the back door & you are on the slope. Enjoy gorgeous ...
From $513 per night (USD)VRBO

















































































