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Guest favorite
Condo in Wintergreen Resort
Overlook 180 degree views w/Peloton!
4 guestsStudio2 beds2 baths
Jun 2 – 7
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Jun 2 – 7
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R23,351 ZAR for 5 nights
for 5 nights

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Guest favorite
Condo in Wintergreen Resort
1 bedroom condo, hiking, breweries, wineries
Free cancellation
Jun 6 – 11
R11,466 ZAR for 5 nights
for 5 nights
4.98 out of 5 average rating, 137 reviews
Superhost
Apartment in Wintergreen Resort
GorgeousView/FrontRowSeat4thFireworks/PupsWelcome!
Free cancellation
Jun 29 – Jul 4
R26,926 ZAR for 5 nights
for 5 nights
New place to stay
Top guest favorite
Condo in Wintergreen Resort
Sunset Vista (Mountain Views) “Skies for Miles”
Free cancellation
May 26 – 31
R15,745 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 234 reviews
Top guest favorite
Condo in Wintergreen Resort
3 BR 3 BA, 2 story condo in Highlands
5 beds
May 19 – 24
R29,822 ZAR for 5 nights
for 5 nights
4.99 out of 5 average rating, 158 reviews
Top guest favorite
Chalet in Wintergreen Resort
Mountain Views, Hiking, Ski-Out @ Tyro
Free cancellation
Jun 1 – 6
R33,963 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 48 reviews
Guest favorite
Townhouse in Wintergreen Resort
Fantastic home in an ideal location, dogs welcome!
5 beds
May 25 – 30
R15,019 ZAR for 5 nights
for 5 nights
4.94 out of 5 average rating, 182 reviews
Top guest favorite
Condo in Wintergreen Resort
Wintergreen! Dog friendly, cozy and comfortable
Free cancellation
Jun 9 – 14
R15,448 ZAR for 5 nights
for 5 nights
4.9 out of 5 average rating, 49 reviews
Top guest favorite
Condo in Wintergreen Resort
Panoramic Mountain View~ Summer Pool~ First Floor
3 beds
May 26 – 31
R21,347 ZAR for 5 nights
for 5 nights
4.97 out of 5 average rating, 107 reviews
Top guest favorite
Home in Wintergreen Resort
Wintergreen condo ski-in/ski-out
4 beds
May 19 – 24
R20,248 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 17 reviews
Top guest favorite
Townhouse in Wintergreen Resort
Beary Lazy - 4 beds and 2 sleeping sofas!
Free cancellation
May 27 – Jun 1
R15,126 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 40 reviews
Guest favorite
Condo in Wintergreen Resort
On the mountain, pet and child friendly
3 beds
May 31 – Jun 5
R13,088 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 19 reviews
Guest favorite
Condo in Wintergreen Resort
Cozy little condo, near slopes.
Free cancellation
May 25 – 30
R12,766 ZAR for 5 nights
for 5 nights
4.98 out of 5 average rating, 50 reviews
Guest favorite
Home in Wintergreen Resort
Ski-In/Ski-Out Renovated Chalet on Lower Tyro
Free cancellation
May 26 – 31
R35,507 ZAR for 5 nights
for 5 nights
4.97 out of 5 average rating, 195 reviews
Top guest favorite
Condo in Wintergreen Resort
A Scenic Mountain Retreat, your Home on the Ridge
3 beds
May 25 – 30
R14,749 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 37 reviews
Top guest favorite
Home in Wintergreen Resort
Premiere 2 BR Getaway Ski In/Out Wintergreen Condo
5 beds
May 27 – Jun 1
R16,520 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 17 reviews
Top guest favorite
Apartment in Wintergreen Resort
Endless Mountain Top Views from All The Way Up!
3 beds
May 25 – 30
R19,113 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 86 reviews
Top guest favorite
Condo in Wintergreen Resort
Lovely 1-BDR condo w/indoor fireplace & ski locker
2 beds
May 25 – 30
R15,147 ZAR for 5 nights
for 5 nights
4.98 out of 5 average rating, 51 reviews
Top guest favorite
Condo in Wintergreen Resort
2 bdrm/2 full bath Best Views of Blue Ridge Mtns.
2 queen beds
Jun 10 – 15
R19,909 ZAR for 5 nights
for 5 nights
4.97 out of 5 average rating, 119 reviews