Book Holiday Homes in Wintergreen

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

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
Book a stay at this family-friendly vacation home in Charlottesville. Enjoy free WiFi, a garden, and patios. Popular attractions Ragged Branch Distillery and ...
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
Book a stay at this family-friendly vacation home in Fairfield. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Brownsburg Historic ...
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
Stay at this vacation home in Roseland. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Wintergreen Resort and Reids Gap Trailhead are ...
Wintergreen Resort Post & Beam Home Beauty
Save an average of 15% on thousands of hotels when you're signed in
The Landmark: Luxury In Downtown Staunton

The Landmark: Luxury In Downtown Staunton

Staunton
Stay at this vacation home in Staunton. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions American Shakespeare Center and The Woodrow ...
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 NZ$744 per night from 13 Apr to 14 Apr
NZ$744
includes taxes & fees
13 Apr - 14 Apr
Stay at this vacation home in Nellysford. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Wintergreen Resort and Raven's Roost Overlook ...
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
Book a stay at this family-friendly vacation home in Roseland. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Wintergreen Resort and ...
NEW! Sleeps 14: Game Room, Fire Pit, & Hot Tub
NEW! Secluded Farmhouse Winery, Hike, Lg Group❤️

NEW! Secluded Farmhouse Winery, Hike, Lg Group❤️

Faber
Book a stay at this family-friendly vacation home in Faber. Enjoy free WiFi, private pools, and a garden. Popular attractions Walton's Mountain Museum and DelFosse ...
NEW! Secluded Farmhouse Winery, Hike, Lg Group❤️
Cozy Country small two bedroom home.

Cozy Country small two bedroom home.

Roseland
The price is NZ$426 per night from 15 Apr to 16 Apr
NZ$426
includes taxes & fees
15 Apr - 16 Apr
Stay at this vacation home in Roseland. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Virginia Blue Ridge Railway ...
Cozy Country small two bedroom home.
Insane Mountain Views - New Listing

Insane Mountain Views - New Listing

Wintergreen Resort
Stay at this vacation home in Roseland. Enjoy patios, an in-room coffeemaker, and in-room fireplaces. Popular attractions Wintergreen Resort and Raven's Roost ...
Insane Mountain Views - New Listing
Don't see what you're looking for?
See all available properties in Wintergreen
View all properties
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
NZ$426
Highest Price
NZ$744
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 NZ$744 per night from 13 Apr to 14 Apr
NZ$744
includes taxes & fees
13 Apr - 14 Apr
Stay at this vacation home in Nellysford. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Wintergreen Resort and Raven's Roost Overlook ...
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
Stay at this condo in Nellysford. Enjoy free WiFi, patios, and an in-room coffeemaker. Our guests praise the helpful staff in our reviews. Popular attractions ...
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
Stay at this condo in Nellysford. Enjoy free WiFi, private pools, and a sauna. Our guests praise the helpful staff in our reviews. Popular attractions Wintergreen ...
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
Stay at this vacation home in Nellysford. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Wintergreen Resort and Raven's Roost Overlook ...
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
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.