Book Holiday Homes in Wintergreen

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Featured Holiday Homes in Wintergreen

Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious

Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious

Charlottesville
Located in Charlottesville, this vacation home is in a rural location, within a 15-minute drive of Ruby Canody Gallery and Ragged Branch Distillery.
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious
Bud's Place, Southern Charm in the Shenandoah Valley of Virginia

Bud's Place, Southern Charm in the Shenandoah Valley of Virginia

Fairfield
Located in Fairfield, this vacation home is in the mountains, within a 10-minute drive of Brownsburg Historic District and Rockbridge Vineyard.
Bud's Place, Southern Charm in the Shenandoah Valley of Virginia
 Wintergreen Resort Post & Beam Home Beauty

Wintergreen Resort Post & Beam Home Beauty

Wintergreen Resort
With a stay at this vacation home in Roseland (Laurel Ridge), you'll be within a 5-minute drive of Wintergreen Resort and George Washington National Forest.
Wintergreen Resort Post & Beam Home Beauty
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The Landmark: Luxury In Downtown Staunton

The Landmark: Luxury In Downtown Staunton

Staunton
With a stay at this vacation home in Staunton, you'll be within a 5-minute walk of The Woodrow Wilson Presidential Library and Mary Baldwin College.
The Landmark: Luxury In Downtown Staunton
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

Roseland
The price is AU$684 per night from 13 Apr to 14 Apr
AU$684
includes taxes & fees
13 Apr - 14 Apr
When you stay at this vacation home in Nellysford, you'll be on a lake, just steps from Wintergreen Resort and George Washington National Forest.
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
NEW! Sleeps 14: Game Room, Fire Pit, & Hot Tub

NEW! Sleeps 14: Game Room, Fire Pit, & Hot Tub

Wintergreen Resort
With a stay at this vacation home in Roseland (Chestnut Springs), you'll be within a 5-minute drive of Wintergreen Resort and George Washington National ...
NEW! Sleeps 14: Game Room, Fire Pit, & Hot Tub
NEW! Secluded Farmhouse Winery, Hike, Lg Group❤️

NEW! Secluded Farmhouse Winery, Hike, Lg Group❤️

Faber
Located in Faber, this vacation home is in the mountains, within a 15-minute drive of DelFosse Vineyards and Winery and Walton's Mountain Museum.
NEW! Secluded Farmhouse Winery, Hike, Lg Group❤️
Cozy Country small two bedroom home.

Cozy Country small two bedroom home.

Roseland
The price is AU$396 per night from 6 Apr to 7 Apr
AU$396
includes taxes & fees
6 Apr - 7 Apr
Located in Roseland, this vacation home is within a 15-minute drive of Virginia Blue Ridge Railway Trail and Woodson's Mill.
Cozy Country small two bedroom home.
Insane Mountain Views - New Listing

Insane Mountain Views - New Listing

Wintergreen Resort
With a stay at this vacation home in Roseland, you'll be steps from Wintergreen Resort and George Washington National Forest.
Insane Mountain Views - New Listing
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Wintergreen Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Wintergreen vacation homes are the perfect way for you to wing it.

Holiday houses in Wintergreen let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Wintergreen in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Wintergreen adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Wintergreen with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Wintergreen vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Wintergreen Holiday Homes essential information

Accommodation
430 Holiday Homes
Lowest Price
AU$396
Highest Price
AU$684
Popular accommodation
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious, Bud's Place, Southern Charm in the Shenandoah Valley of Virginia, Wintergreen Resort Post & Beam Home Beauty, The Landmark: Luxury In Downtown Staunton, Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House., NEW! Sleeps 14: Game Room, Fire Pit, & Hot Tub, NEW! Secluded Farmhouse Winery, Hike, Lg Group❤️, Cozy Country small two bedroom home., Insane Mountain Views - New Listing

Top trending hotels in Wintergreen

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

Roseland
The price is AU$684 per night from 13 Apr to 14 Apr
AU$684
includes taxes & fees
13 Apr - 14 Apr
When you stay at this vacation home in Nellysford, you'll be on a lake, just steps from Wintergreen Resort and George Washington National Forest.
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

Roseland
When you stay at this condo in Nellysford, you'll be in the mountains, just steps from Wintergreen Resort and George Washington National Forest.
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
Best views on Mountain! Breathtaking 5 Star. APRIL-Spring available! BOOK NOW!

Best views on Mountain! Breathtaking 5 Star. APRIL-Spring available! BOOK NOW!

Wintergreen
With a stay at this condo in Nellysford, you'll be in the mountains, just a 1-minute walk from George Washington National Forest and 8 minutes by foot from Bold ...
Best views on Mountain! Breathtaking 5 Star. APRIL-Spring available! BOOK NOW!
Save an average of 15% on thousands of hotels when you're signed in
Custom Builder just completely  remodeled this Mountain Chalet! ...with Hot Tub!

Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!

Wintergreen Resort
With a stay at this vacation home in Nellysford (Treeloft), you'll be steps from Wintergreen Resort and George Washington National Forest.
Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!
Don't see what you're looking for?
See all available properties in Wintergreen
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.