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Search results; Over 1,000 homes in Winter Park

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Featured hotel
Room in Winter Park
ADA premium double queen twin bunks
1 bedroom, 1 private bathroom
1–6 Sept
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Superhost
Townhouse in Fraser
Luxury Grand Park Retreat with Private Hot Tub
4 bedrooms, 8 beds
1–6 Sept
New place to stay
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Guest favourite
Home in Winter Park
Luxury Winter Park HomeHotTub*Majestic View*Resort
4 bedrooms, 9 beds
13–18 Sept
4.97 out of 5 average rating, 33 reviews
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Superhost
Apartment in Winter Park
WP Mountain Retreat • 3BR/2BA • 3 Hot Tubs & Pool
3 bedrooms, 7 beds
12–17 Sept
4.87 out of 5 average rating, 121 reviews
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Guest favourite
Apartment in Fraser
Spacious Family Friendly Townhome Retreat
3 bedrooms, 6 beds
6–11 Sept
4.97 out of 5 average rating, 30 reviews
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Guest favourite
Cabin in Winter Park
Cabin w/ Deck- Bike & HikeTrails & Downtown- RMNP
5 bedrooms, 5 beds
6–11 Sept
4.86 out of 5 average rating, 21 reviews
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Superhost
Home in Winter Park
Downtown WP Villa 165 - Hot Tub - Views - Bunks
4 bedrooms, 7 beds
1–6 Sept
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Flat in Winter Park
The real Winter Park/Alpine experience condo
1 bedroom, 2 beds
8–13 Sept
5.0 out of 5 average rating, 4 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
12–17 Sept
5.0 out of 5 average rating, 25 reviews
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Guest favourite
Townhouse in Fraser
Ridgetop Townhome with Panoramic Mountain Views
3 bedrooms, 4 beds
7–12 Sept
4.72 out of 5 average rating, 109 reviews
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Superhost
Home in Winter Park
Unbeatable Location Downtown Winter Park W/Hot tub
4 bedrooms, 7 beds
1–6 Sept
New place to stay
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Superhost
Home in Winter Park
Luxury Emerald Escape | Hot Tub | Ski Shuttle
3 bedrooms, 5 beds
9–14 Sept
New place to stay
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Guest favourite
Townhouse in Winter Park
Row 41 | 4BR, Rooftop Hot Tub, Walk to Town
4 bedrooms, 5 beds
1–6 Sept
5.0 out of 5 average rating, 22 reviews
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Top guest favourite
Townhouse in Winter Park
The Camping Bear
4 bedrooms, 7 beds
14–19 Sept
4.92 out of 5 average rating, 78 reviews
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Superhost
Home in Winter Park
Chalet Apres | Amazing Location | Hot Tub & Sauna
2 bedrooms, 3 beds
1–6 Sept
4.75 out of 5 average rating, 24 reviews
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Top guest favourite
Home in Fraser
Spruce Ridge Villa 714H - Great Views - Bunk Room
3 bedrooms, 5 beds
13–18 Sept
5.0 out of 5 average rating, 13 reviews
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Guest favourite
Home in Winter Park
LUX Chateau Louise • Unique • Walk to Everything
3 bedrooms, 5 beds
1–6 Sept
5.0 out of 5 average rating, 13 reviews
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Guest favourite
Townhouse in Winter Park
Beautiful Townhome in Downtown Winter Park!
4 bedrooms, 7 beds
8–13 Oct
4.9 out of 5 average rating, 234 reviews
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Luxe
Home in Winter Park
Ski In Out Chalet 277 - Hot Tub - Great Views
4 bedrooms, 13 beds
6–11 Sept
4.94 out of 5 average rating, 72 reviews