Search results; Over 1,000 homes in Winter Park

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Guest favorite
Home in Winter Park
Winter Park Creekside Chalet with Hot Tub
13 guests4 bedrooms8 beds3 baths
Aug 24 – 29
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Aug 24 – 29
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R50,250 ZAR for 5 nights

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Condo in Winter Park
Slopeside Studio
Free cancellation
Aug 10 – 15
R8,725 ZAR for 5 nights
New place to stay
Apartment in Winter Park
Studio Mountainview 4th-Floor | Kitchenette
2 beds
Aug 3 – 8
R8,404 ZAR for 5 nights
4.62 out of 5 average rating, 39 reviews
Superhost
Cabin in Winter Park
Gondola Gem 1BR w/ Mountain Views & Hot Tub Access
2 beds
Aug 9 – 14
R14,177 ZAR for 5 nights
New place to stay
Guest favorite
Condo in Winter Park
One Bdrm Condo Ski In / Ski Out, Hot Tub, Fire Pit
2 beds
Aug 3 – 8
R12,702 ZAR for 5 nights
4.87 out of 5 average rating, 186 reviews
Guest favorite
Condo in Winter Park
Studio Condo in the Heart of Winter Park! lic#9602
3 beds
Aug 2 – 7
R11,954 ZAR for 5 nights
4.89 out of 5 average rating, 132 reviews
Condo in Winter Park
Slopeside Studio Mountainview 4th-Floor
2 beds
Aug 1 – 6
R9,088 ZAR for 5 nights
4.2 out of 5 average rating, 35 reviews
Guest favorite
Condo in Winter Park
Ski-In Ski-Out Zephyr Mtn Lodge Condo w/ Hot Tub
2 beds
Aug 3 – 8
R12,655 ZAR for 5 nights
4.89 out of 5 average rating, 222 reviews
Superhost
Townhouse in Winter Park
Bullseye Retreat | Sleeps 10! | Mtn View & HotTub!
Free cancellation
Aug 3 – 8
R40,200 ZAR for 5 nights
Guest favorite
Condo in Winter Park
2BR Ski-In Ski-Out w/ Desirable Amenities
4 beds
Aug 1 – 6
R23,949 ZAR for 5 nights
5.0 out of 5 average rating, 8 reviews
Top guest favorite
Condo in Fraser
Updated Condo | Washer Dryer | Steps to Shuttle
2 beds
Aug 3 – 8
R12,830 ZAR for 5 nights
4.98 out of 5 average rating, 131 reviews
Superhost
Condo in Winter Park
Fantastic front corner 2bd condo Base Winter Park
2 king beds
Aug 5 – 10
R19,867 ZAR for 5 nights
New place to stay
Superhost
Home in Winter Park
Winter Park Condo
2 beds
Aug 3 – 8
R11,440 ZAR for 5 nights
4.75 out of 5 average rating, 24 reviews
Guest favorite
Guest suite in Fraser
Spring has arrived!
Free cancellation
Aug 11 – 16
R8,019 ZAR for 5 nights
4.92 out of 5 average rating, 643 reviews
Top guest favorite
Condo in Winter Park
Lovely Studio at Winter Park Resort Ski In & Out
1 queen bed
Aug 1 – 6
R13,557 ZAR for 5 nights
4.92 out of 5 average rating, 64 reviews
Superhost
Home in Winter Park
Luxury Villa 568 I Free Adventures Daily
5 beds
Aug 4 – 9
R23,734 ZAR for 5 nights
New place to stay
Apartment in Winter Park
In-town studio with indoor pool, hot tubs & gym
2 beds
Aug 3 – 8
R10,478 ZAR for 5 nights
4.82 out of 5 average rating, 28 reviews
Guest favorite
Condo in Winter Park
Homebase Snowblaze
2 beds
Aug 1 – 6
R13,686 ZAR for 5 nights
4.87 out of 5 average rating, 222 reviews
Top guest favorite
Townhouse in Winter Park
2 Main Level Primary Suites, Hot Tub & Great Views
5 beds
Aug 1 – 6
R30,422 ZAR for 5 nights
5.0 out of 5 average rating, 6 reviews