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Search results; Over 1,000 homes in Winter Park

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Guest favourite
Apartment in Winter Park
10 min to Resort! Amazing Views & Sauna!
3 bedrooms, 3 beds, 2 private bathrooms
28 Sept – 3 Oct
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4.95 out of 5 average rating, 157 reviews
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Guest favourite
Cabin in Winter Park
Cabin w/ Deck- Bike & HikeTrails & Downtown- RMNP
5 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
4.86 out of 5 average rating, 22 reviews
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Superhost
Apartment in Winter Park
WP Mountain Retreat • 3BR/2BA • 3 Hot Tubs & Pool
3 bedrooms, 7 beds, 2 bathrooms
27 Sept – 2 Oct
4.87 out of 5 average rating, 123 reviews
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Guest favourite
Flat in Winter Park
The Little Palace-Full Amenities
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
4.89 out of 5 average rating, 54 reviews
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Superhost
Home in Winter Park
Downtown WP Chalet 380 - Hot Tub - Great Views
3 bedrooms, 6 beds, 3.5 bathrooms
20–25 Sept
New place to stay
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Top guest favourite
Home in Fraser
Mountain Retreat | New Condo | Private Hot Tub
2 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 87 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
Home in Winter Park
Winter Park Pond Chalet 13 - Hot Tub - Views
4 bedrooms, 5 beds, 4 bathrooms
11–16 Oct
4.77 out of 5 average rating, 22 reviews
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Top guest favourite
Apartment in Winter Park
Private Hot Tub + Free Shuttle | Walk Downtown
2 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 41 reviews
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Top guest favourite
Apartment in Winter Park
The Rustic Moose
2 bedrooms, 6 beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 71 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, 1 bathroom
11–16 Oct
4.88 out of 5 average rating, 221 reviews
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Guest favourite
Apartment in Winter Park
Winter Park Condo w/ Fireplace, Centrally Located
2 bedrooms, 3 beds, 2 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 6 reviews
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Top guest favourite
Home in Winter Park
Winter Park Home | Hot Tub Sauna Walk to Downtown
4 bedrooms, 5 beds, 3.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 19 reviews
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Guest favourite
Apartment in Fraser
Alpine Luxe Loft- Hot Tub, Fireplace, Views, Ski
3 bedrooms, 4 beds, 2 bathrooms
1–6 Nov
4.91 out of 5 average rating, 33 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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Guest favourite
Home in Winter Park
Luxurious Mountain Home near Downtown Winter Park!
7 bedrooms, 17 beds, 6.5 bathrooms
24–29 Sept
4.89 out of 5 average rating, 87 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, 1 bathroom
20–25 Sept
4.96 out of 5 average rating, 164 reviews
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Luxe
Home in Winter Park
Ski In Out Chalet 277 - Hot Tub - Great Views
4 bedrooms, 13 beds, 4.5 bathrooms
27 Sept – 2 Oct
4.94 out of 5 average rating, 72 reviews
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Top guest favourite
Home in Winter Park
Luxury Winter Park HomeHotTub*Majestic View*Resort
4 bedrooms, 9 beds, 4 bathrooms
18–23 Oct
4.97 out of 5 average rating, 36 reviews