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Search results; Over 1,000 homes in Winter Park

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Top guest favourite
Townhouse in Winter Park
Winter Park Townhome w/ Stunning Slope Views!
3 bedrooms, 6 beds, 2.5 private bathrooms
13–18 Oct
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4.94 out of 5 average rating, 163 reviews
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Guest favourite
Apartment in Winter Park
One Bdrm Condo Ski In / Ski Out, Hot Tub, Fire Pit
1 bedroom, 2 beds
11–16 Oct
4.88 out of 5 average rating, 221 reviews
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Guest favourite
Cabin in Winter Park
Cabin w/ Deck- Bike & HikeTrails & Downtown- RMNP
5 bedrooms, 5 beds
19–24 Sept
4.86 out of 5 average rating, 22 reviews
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Guest favourite
Flat in Winter Park
The Little Palace-Full Amenities
1 bedroom, 2 beds
20–25 Sept
4.89 out of 5 average rating, 54 reviews
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Superhost
Apartment in Winter Park
WP Mountain Retreat • 3BR/2BA • 3 Hot Tubs & Pool
3 bedrooms, 7 beds
27 Sept – 2 Oct
4.87 out of 5 average rating, 123 reviews
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Top guest favourite
Home in Fraser
Mountain Retreat | New Condo | Private Hot Tub
2 bedrooms, 4 beds
19–24 Sept
4.97 out of 5 average rating, 87 reviews
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Top guest favourite
Apartment in Winter Park
The Rustic Moose
2 bedrooms, 6 beds
19–24 Sept
5.0 out of 5 average rating, 71 reviews
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Top guest favourite
Flat in Winter Park
Hip Ski Pad • Hot Tub • Steps to Downtown
2 beds
20–25 Sept
4.85 out of 5 average rating, 39 reviews
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Top guest favourite
Townhouse in Winter Park
The Camping Bear
4 bedrooms, 7 beds
5–10 Oct
4.92 out of 5 average rating, 78 reviews
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Top guest favourite
Apartment in Winter Park
Winter Park Studio: On the River~ Walk Downtown!
2 beds
6–11 Oct
4.98 out of 5 average rating, 436 reviews
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Top guest favourite
Apartment in Winter Park
Private Hot Tub + Free Shuttle | Walk Downtown
2 bedrooms, 3 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 41 reviews
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Top guest favourite
Apartment in Winter Park
Top floor, larger 1 bedroom in Winter Park Village
1 bedroom, 2 beds
20–25 Sept
4.96 out of 5 average rating, 164 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
27 Sept – 2 Oct
5.0 out of 5 average rating, 28 reviews
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Top guest favourite
Apartment in Fraser
Walk to Restaurants! Enjoy Cool Fall Days!
1 bedroom, 3 beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 148 reviews
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Top guest favourite
Apartment in Winter Park
Ski In/Ski Out - Modern Cozy Condo in Winter Park
2 beds
20–25 Sept
4.9 out of 5 average rating, 249 reviews
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Guest favourite
Apartment in Winter Park
Prime location, amazing views, stylish, sleeps 7
2 bedrooms, 5 beds
20–25 Sept
4.87 out of 5 average rating, 119 reviews
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Guest favourite
Apartment in Winter Park
Winter Park Condo w/ Fireplace, Centrally Located
2 bedrooms, 3 beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 6 reviews
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Top guest favourite
Flat in Winter Park
New Hike or Ski in/out Modern Condo-Quiet w/ Views
2 bedrooms, 4 beds
3–8 Oct
5.0 out of 5 average rating, 42 reviews
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Guest favourite
Flat in Winter Park
Sleeper@SnowBlaze! Great Location! Hot Tubs/Pool!
1 queen bed
25–30 Sept
4.93 out of 5 average rating, 135 reviews