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Guest favorite
Chalet in Wintergreen Resort
Brown Bear Lodge: Walk to Ski + Hot Tub + Mtn Vibe
8 guests3 bedrooms6 beds2.5 baths
Jun 1 – 6
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Jun 1 – 6
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R20,991 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
R11,293 ZAR for 5 nights
for 5 nights
4.97 out of 5 average rating, 138 reviews
Top guest favorite
Condo in Wintergreen Resort
Sunset Vista (Mountain Views) “Skies for Miles”
Free cancellation
Jun 1 – 6
R15,308 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 234 reviews
Top guest favorite
Condo in Wintergreen Resort
Cozy Comfort with a View - Wintergreen Resort
Free cancellation
Jun 7 – 12
R14,312 ZAR for 5 nights
for 5 nights
4.9 out of 5 average rating, 142 reviews
Top guest favorite
Condo in Wintergreen Resort
Cozy, clean, quiet mountain condo- King bed
2 beds
Jun 1 – 6
R11,312 ZAR for 5 nights
for 5 nights
4.94 out of 5 average rating, 248 reviews
Guest favorite
Townhouse in Wintergreen Resort
King Bed Pool Tennis Golf Hiking DogOK Pack n Play
4 beds
Jun 8 – 13
R11,025 ZAR for 5 nights
for 5 nights
4.96 out of 5 average rating, 28 reviews
Guest favorite
Condo in Wintergreen Resort
Balcony Pool Tennis Golf Hiking Pack 'n Play Roku
2 king beds
Jun 14 – 19
R10,495 ZAR for 5 nights
for 5 nights
4.89 out of 5 average rating, 63 reviews
Top guest favorite
Home in Wintergreen Resort
Cozy Chalet | King Beds | Fireplace | Hot Tub
2 king beds
Jul 6 – 11
R19,840 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 106 reviews
Top guest favorite
Apartment in Wintergreen Resort
Endless Mountain Top Views from All The Way Up!
3 beds
Jun 19 – 24
R24,998 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 87 reviews
Superhost
Apartment in Wintergreen Resort
Wintergreen Getaway
Free cancellation
Jun 1 – 6
R8,905 ZAR for 5 nights
for 5 nights
4.9 out of 5 average rating, 52 reviews
Guest favorite
Condo in Wintergreen Resort
Mountain top 3-bedroom condo with spectacular view
Free cancellation
Jun 2 – 7
R22,305 ZAR for 5 nights
for 5 nights
4.94 out of 5 average rating, 100 reviews
Guest favorite
Condo in Wintergreen Resort
Cozy little condo, near slopes.
Free cancellation
Jun 1 – 6
R12,616 ZAR for 5 nights
for 5 nights
4.98 out of 5 average rating, 50 reviews
Home in Wintergreen Resort
Ski in Style @ Sapphire Squirrel
3 beds
Jun 1 – 6
R18,415 ZAR for 5 nights
for 5 nights
New place to stay
Guest favorite
Condo in Wintergreen Resort
BlueRidge Getaway- Dog Friendly
6 beds
Jun 8 – 13
R15,266 ZAR for 5 nights
for 5 nights
4.94 out of 5 average rating, 133 reviews
Top guest favorite
Condo in Wintergreen Resort
All-Season 2bd/2ba next to Spa view of Golf Course
5 beds
Jun 1 – 6
R17,387 ZAR for 5 nights
for 5 nights
4.95 out of 5 average rating, 130 reviews
Top guest favorite
Condo in Wintergreen Resort
3 BR 3 BA, 2 story condo in Highlands
Free cancellation
Jun 1 – 6
R29,471 ZAR for 5 nights
for 5 nights
4.99 out of 5 average rating, 159 reviews
Guest favorite
Condo in Wintergreen Resort
Cozy Condo in Wintergreen Resort That Sleeps 4!
Free cancellation
Jun 1 – 6
R14,736 ZAR for 5 nights
for 5 nights
4.86 out of 5 average rating, 28 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
R19,676 ZAR for 5 nights
for 5 nights
4.97 out of 5 average rating, 119 reviews
Top guest favorite
Condo in Wintergreen Resort
A Scenic Mountain Retreat, your Home on the Ridge
3 beds
Jun 8 – 13
R14,577 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 38 reviews