Wintergreen Resort Vacation Rentals

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Make Wintergreen Resort your next getaway

Wintergreen Resort, VA vacation rentals

Top Wintergreen Resort property types

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Apartments

View 15 Apartments
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House rentals

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Cottages

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Popular amenities for Wintergreen Resort vacation rentals

Popular
Dog-friendly Hot tub Internet
Snug Wintergreen Resort Studio: Ski In & Out!
0 Bedroom | 1 Bath | Sleeps 5

Snug Wintergreen Resort Studio: Ski In & Out! - Wintergreen Resort, VA

$133 avg / night
(excludes fees and taxes)
5.0 (3)
All-Season Fun! Wintergreen Resort Condo w/ Views
4 Bedroom | 2.5 Bath | Sleeps 15

All-Season Fun! Wintergreen Resort Condo w/ Views - Wintergreen Resort, VA

$150 avg / night
(excludes fees and taxes)
5.0 (3)
Cozy Wintergreen Resort Condo: Walk to Ski Lifts!
2 Bedroom | 2 Bath | Sleeps 4

Cozy Wintergreen Resort Condo: Walk to Ski Lifts! - Wintergreen Resort, VA

$150 avg / night
(excludes fees and taxes)
4.56 (9)
Wintergreen Resort Condo w/ Deck, 0.3 Mi to Slopes
1 Bedroom | 1 Bath | Sleeps 4

Wintergreen Resort Condo w/ Deck, 0.3 Mi to Slopes - Wintergreen Resort, VA

$109 avg / night
(excludes fees and taxes)
4.5 (2)
Pool Access: Scenic Condo in Wintergreen Resort!
1 Bedroom | 2 Bath | Sleeps 6

Pool Access: Scenic Condo in Wintergreen Resort! - Wintergreen Resort, VA

$150 avg / night
(excludes fees and taxes)
5.0 (1)

View 24 more homes

Browse more vacation rental amenities in Wintergreen Resort

Pool | Lake view | Ski-in/ski-out | Water view | Waterfront | A/C | Washer/dryer | Balcony | Ping-pong table | Pool table

Recent Wintergreen Resort guest reviews

Had a wonderful girls trip for several days. The house was beautiful and well maintained. It is exactly how it looked in the pictures. We had a slight plumbing issue which was addressed immediately. While the winding road did cause us some concerns, we were on the mountain, what did we expect. There were two very slight concerns. One was the mattresses in the twin room were extremely uncomfortable. While they probably are fine for children, they are not for adult use. Second, there is a portion of the driveway way looks like there has been some erosion that needs repair. Very minor when compared to the overall condition of this house. I would definitely recommend this home as a unique and wonderful experience whether you are looking for a quick mountain visit or a long term monthly rental.
Betsy . | Apr 2026
We had a great time at the house! Was super easy to ski up and cross a small parking area and be at the house. It had all that was shown and was perfect for a family getaway with 6 adults!
Samantha . | Feb 2026
We thoroughly enjoyed our time at this beautiful home in Wintergreen. The house is nicely decorated and in a beautiful location. We visited for a ski weekend and really enjoyed being able to ski-in and ski-out of this location. The separate living spaces were an added bonus as we were a larger group, these separate spaces gave everyone space to spread out. We would definitely stay again.
Whitney . | Jan 2026
Wintergreen Resort vacation rental FAQ

Yes, 7 of our Wintergreen Resort homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 40 of our Wintergreen Resort vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Wintergreen Resort vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find the check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Wintergreen Resort team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for Wintergreen Resort, log in to Trip Manager to explore the options available for your specific trip.

Book confidently. Stay comfortably.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
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Seamless check-in
Vacasa Guest Value Prop Icons cleaning
Professional cleaning

Nearby destinations

Appalachian Mountains   |   Blue Ridge Parkway   |   Nellysford   |   Lyndhurst   |   Massies Mill   |   Roseland   |   Staunton   |   Grottoes   |   Weyers Cave   |   Virginia
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