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Search results; Over 1,000 homes in Winter Park

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Top guest favourite
Guest suite in Winter Park
Charming Suite in Old Town Winter Park
1 bedroom, 1 bed, 1 private bathroom
20–25 Sept
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4.98 out of 5 average rating, 499 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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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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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
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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Top guest favourite
Apartment in Winter Park
Winter Park Studio: On the River~ Walk Downtown!
2 beds, 1 bathroom
19–24 Oct
4.98 out of 5 average rating, 437 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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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
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
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
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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
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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Luxe
Townhouse in Winter Park
Lakota SkiRenity | Private Hot Tub
3 bedrooms, 6 beds, 3.5 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 7 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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Top guest favourite
Apartment in Winter Park
Downtown Mtn Oasis + Hot Tubs | Steps to Events
2 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
4.96 out of 5 average rating, 114 reviews
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Top guest favourite
Apartment in Fraser
Walk to Restaurants! Enjoy Cool Fall Days!
1 bedroom, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 149 reviews
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Guest favourite
Apartment in Winter Park
Prime location, amazing views, stylish, sleeps 7
2 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.87 out of 5 average rating, 119 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
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