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Search results; Over 1,000 homes in Winter Park

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Top guest favourite
Flat in Winter Park
Luxury Winter Park Studio*PrivHotTub*Majestic View
1 bedroom, 1 bed, 1 private bathroom
15–20 Nov
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4.97 out of 5 average rating, 135 reviews
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Featured hotel
Hotel in Winter Park
Gravity Haus Winter Park, Superior king twin trun.
1 bedroom
3–8 Oct
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Top guest favourite
Home in Winter Park
Luxury Winter Park HomeHotTub*Majestic View*Resort
4 bedrooms, 9 beds
18–23 Oct
4.97 out of 5 average rating, 37 reviews
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Guest favourite
Cabin in Winter Park
Cozy Cabin in Perfect Location
2 beds
7–12 Oct
4.84 out of 5 average rating, 659 reviews
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Superhost
Home in Winter Park
Luxury Emerald Escape | Hot Tub | Ski Shuttle
3 bedrooms, 5 beds
6–11 Oct
New place to stay
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Guest favourite
Apartment in Winter Park
10 Minute Walk to the Winter Park Gondola 6 beds.
3 bedrooms, 6 beds
15–20 Oct
4.94 out of 5 average rating, 69 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
4–9 Oct
5.0 out of 5 average rating, 29 reviews
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Guest favourite
Apartment in Winter Park
Stylish Studio on Main Street in Winter Park
1 king bed
6–11 Oct
4.9 out of 5 average rating, 98 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
4–9 Oct
4.88 out of 5 average rating, 221 reviews
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Superhost
Home in Winter Park
Rocky Mountain Divide
5 bedrooms, 7 beds
6–11 Oct
New place to stay
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Top guest favourite
Guest suite in Winter Park
Charming Suite in Old Town Winter Park
1 bedroom, 1 queen bed
1–6 Oct
4.98 out of 5 average rating, 499 reviews
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Top guest favourite
Flat in Winter Park
Modern New build ski in/out. 1br + den.
1 bedroom, 4 beds
16–21 Oct
5.0 out of 5 average rating, 49 reviews
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Top guest favourite
Townhouse in Winter Park
Winter Park Townhome w/ Stunning Slope Views!
3 bedrooms, 6 beds
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
4–9 Oct
5.0 out of 5 average rating, 121 reviews
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Superhost
Home in Winter Park
WP Resort Villa 509 - Hot Tub - Views - Theatre
4 bedrooms, 6 beds
1–6 Oct
New place to stay
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Top guest favourite
Flat in Winter Park
Mountain Condo w/ Hot Tub | Walk to Town | Ski Bus
2 bedrooms, 4 beds
4–9 Oct
5.0 out of 5 average rating, 22 reviews
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Guest favourite
Home in Winter Park
The Owl's Nest | Private Hot Tub | Game Room
4 bedrooms, 9 beds
11–16 Oct
5.0 out of 5 average rating, 10 reviews
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Guest favourite
Home in Winter Park
Winter Park Pond Chalet 13 - Hot Tub - Views
4 bedrooms, 5 beds
4–9 Oct
4.78 out of 5 average rating, 23 reviews
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Top guest favourite
Apartment in Fraser
Luxury Condo w Private Hot Tub - Fraser, CO
2 bedrooms, 3 beds
27 Oct – 1 Nov
5.0 out of 5 average rating, 42 reviews