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Ski-in/Ski-out vacation rentals in Wintergreen Resort

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Top-rated ski-in/ski-out rentals in Wintergreen Resort

Guests agree: these ski-in/ski-out homes are highly rated for location, cleanliness, and more.

Guest favorite
Home in Wintergreen Resort
Ski-In/Ski-Out Renovated Chalet on Lower Tyro
Completely renovated, 3 BR/2BA chalet, located on Lower Tyro slope, just below Tequila. Rustic decor, fully stocked kitchen, high end appliances, granite counters. Open floor plan, walls of windows, mtn views. Beautiful stone fireplace, ample comfortable seating. 2 main floor Masters, each w/King bed, TV, luxurious bedding. Loft is a dedicated kids space: 2 sets of bunks, daybed w/trundle, TV & PS4. Gas grill, 6 person hot tub. Perfect ski home to host 2 Families, or a romantic couple's getaway.
Jun 18 – 25
$273 per night
Guest favorite
Condo in Wintergreen Resort
A True Mountain Getaway! Ski in/Ski out!
Located steps away from the top of the ski slopes at Wintergreen Resort. No snow? No problem! Enjoy the cool mountain breezes, hiking and climbing trails, mountain lakes with beaches, wineries, breweries and much much more. Restaurants and shopping within walking distance. Our place has a galley kitchen and small refrigerator, a large deck to enjoy a quiet dinner and has been newly decorated. There is a king sized bed and a smaller fold out sofa that could accommodate two small children.
Jul 23 – 30
$92 per night
Guest favorite
Condo in Wintergreen Resort
Amazing Blue Ridge ski-front views with Wintermint
Experience one of the best year-round locations at Wintergreen in this 1 bedroom/1 bath, slope-front 1.5 level condo in the heart of the Wintergreen Resort! This incredible spot offers a quiet and cozy getaway for 2 guests seeking adventure or nothing at all. Enjoy the ability to ski-in/out from the property during the wintertime and explore the hiking trails during the summer. It's a short walk to the Mountain Inn (next door), 3 restaurants/bars, shopping, Starbucks, and outdoor activities.
Mar 12 – 19
$97 per night

Popular amenities for Wintergreen Resort ski-in/ski-out rentals

Ski-in/ski-out house rentals

Superhost
Home in Wintergreen Resort
Ski In/Ski Out House, top of Eagle/Tyro, Views
Dec 18 – 25
$328 per night
Guest favorite
Home in Wintergreen Resort
Amazing 5 bed/4 bath ski front home with hot tub!
May 28 – Jun 4
$385 per night
Guest favorite
Home in Wintergreen Resort
Treeloft 17: Ski in/ski out – EV charger – 3BR/3BA
Mar 12 – 19
$222 per night
Guest favorite
Home in Wintergreen Resort
Ski-in/out condo with year-round mountain views
Sep 1 – 8
$160 per night
Superhost
Home in Wintergreen Resort
Walk to Ski! Seasonal MNT Views!
May 3 – 10
$225 per night
Superhost
Home in Wintergreen Resort
Walk to Ski! HotTub+PoolTable+Shuffleboard+DogsOK
May 6 – 13
$496 per night
Guest favorite
Home in Wintergreen Resort
Top of the Lift Mountain Getaway
Nov 24 – Dec 1
$258 per night
Guest favorite
Home in Wintergreen Resort
Ski-In/Out @ Tyro + Scenic Mountain Views
Apr 9 – 16
$251 per night
Home in Nellysford
Oak Haven
Aug 4 – 11
$261 per night
Guest favorite
Home in Wintergreen Resort
Wintergreen Condo~ 1 Minute To Four Seasons Resort
Apr 23 – 30
$170 per night
Guest favorite
Home in Wintergreen Resort
Luxe Modern Retreat: Steps to Ski & Hike! Views!
Mar 10 – 17
$265 per night
Guest favorite
Home in Wintergreen Resort
ski in/out hot-tub Sauna, dog friendly, amenities
Aug 7 – 14
$579 per night

Family-friendly, ski-in/ski-out home rentals

Superhost
Home in Wintergreen Resort
Walk to Ski! Dogs OK+Fireplace+Hiking+Pack 'n Play
Mar 26 – Apr 2
$106 per night
Guest favorite
Home in Wintergreen Resort
Slopes @ Tyro
Jun 6 – 13
$509 per night
Guest favorite
Condo in Wintergreen Resort
Breathtaking Views from The Ledges
Nov 30 – Dec 7
$285 per night
Condo in Wintergreen Resort
Slope Side 2 Bed Condo. Location Location Location
Jun 13 – 20
$203 per night
Guest favorite
Home in Roseland
Tyro Slope Side Home Ski In/Out w/ Yr Round Views
Jul 30 – Aug 6
$143 per night
Guest favorite
Home in Wintergreen Resort
New! Fantastic mountain condo right at the slopes!
Apr 30 – May 7
$111 per night
Guest favorite
Home in Wintergreen Resort
3min to Ski! Dogs OK+Fireplace+Foosball+Roku+Hike
May 21 – 28
$158 per night

Ski-in/ski-out cabin rentals

Guest favorite
Cabin in Wintergreen Resort
Bide-a-Wee- Hike to the Trail Walk to the slopes!
Nov 9 – 16
$210 per night
Guest favorite
Cabin in Wintergreen Resort
A warm mountain top home, steps from the slopes.
Jul 28 – Aug 4
$172 per night
Superhost
Cabin in Wintergreen Resort
COZY A-Frame Spacious Deck w/ Grill
Mar 14 – 21
$177 per night
Guest favorite
Cabin in Wintergreen Resort
Winter Retreat at Oak Ledge: Ski Tips & Cozy Sips
Apr 28 – May 5
$208 per night
Superhost
Cabin in Wintergreen Resort
Slope Side Suite
Jun 19 – 26
$128 per night
Guest favorite
Cabin in Wintergreen
Eagle's Lookout Retreat at Wintergreen Resort, VA
Mar 9 – 16
$243 per night
Superhost
Cabin in Wintergreen Resort
Smoky Bear Cabin
Jun 30 – Jul 7
$170 per night

Destinations to explore