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Search results; Over 1,000 homes in Winter Park

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Top guest favourite
Apartment in Winter Park
Top Floor Condo Steps From Free Shuttle w/Hot Tub
2 bedrooms, 2 beds, 2 private bathrooms
20–25 Sept
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4.93 out of 5 average rating, 289 reviews
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Top guest favourite
Home in Winter Park
WP Resort Villa 502 - Hot Tub - Bunks - Great View
3 bedrooms, 7 beds, 3.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 28 reviews
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Top guest favourite
Guest suite in Winter Park
Charming Suite in Old Town Winter Park
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 499 reviews
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Guest favourite
Flat in Winter Park
Ski in / Ski out at Winter Park - pool & hot tub
2 beds, 1 bathroom
24–29 Sept
4.95 out of 5 average rating, 19 reviews
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Guest favourite
Apartment in Winter Park
Cozy mountain retreat in downtown Winter Park
1 bedroom, 3 beds, 1 bathroom
20–25 Sept
4.94 out of 5 average rating, 165 reviews
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Guest favourite
Flat in Winter Park
Cozy Winter Park Condo - Heart of Town
1 bedroom, 2 beds, 1 bathroom
29 Sept – 4 Oct
4.95 out of 5 average rating, 22 reviews
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Top guest favourite
Townhouse in Winter Park
Winter Park Townhome w/ Stunning Slope Views!
3 bedrooms, 6 beds, 2.5 bathrooms
13–18 Oct
4.94 out of 5 average rating, 163 reviews
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Top guest favourite
Apartment in Winter Park
Cozy Winter Park Riverfront Studio~ Walk Downtown
2 beds, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 121 reviews
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Top guest favourite
Apartment in Winter Park
Winter Park Ski Resort - Top Floor
1 bedroom, 1 sofa bed, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 41 reviews
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Top guest favourite
Flat in Winter Park
Modern New build ski in/out. 1br + den.
1 bedroom, 4 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 48 reviews
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Top guest favourite
Apartment in Winter Park
Cozy DT condo mins from slopes
2 bedrooms, 3 beds, 2 bathrooms
5–10 Oct
5.0 out of 5 average rating, 106 reviews
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Top guest favourite
Apartment in Winter Park
Downtown Mtn Oasis + Hot Tubs | Steps to Events
2 bedrooms, 5 beds, 3 bathrooms
19–24 Sept
4.96 out of 5 average rating, 114 reviews
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Top guest favourite
Apartment in Winter Park
Ski-in Ski-out Cozy Condo
1 queen bed, 1 bathroom
14–19 Oct
4.97 out of 5 average rating, 72 reviews
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Top guest favourite
Guest suite in Fraser
The Mountains are calling!
1 queen bed, 1 bathroom
11–16 Oct
4.92 out of 5 average rating, 704 reviews
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Guest favourite
Apartment in Winter Park
Large studio condo downtown Winter Park, CO
1 queen bed, 1 bathroom
19–24 Sept
4.93 out of 5 average rating, 98 reviews
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Guest favourite
Guest suite in Winter Park
New Look! Breakfast, Hot Tub & No Host fee!
1 bedroom, 1 king bed, 1 bathroom
20–25 Sept
4.84 out of 5 average rating, 474 reviews
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Top guest favourite
Apartment in Winter Park
Ski In/Ski Out - Modern Cozy Condo in Winter Park
2 beds, 1 bathroom
20–25 Sept
4.9 out of 5 average rating, 250 reviews
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Apartment in Winter Park
Stylish 2 BR Condo with Hot Tub and Ski Locker
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
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Guest favourite
Flat in Winter Park
Winter Park 2 bedrooms Corner Unit w outdoor patio
2 bedrooms, 4 beds, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 32 reviews