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Search results; Over 1,000 homes in Winter Park

Guest favourite
Chalet in Winter Park
Riverside Location | Walk To Downtown
4 bedrooms, 5 beds, 3.5 private bathrooms
9–14 Sept
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5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Winter Park
WP Resort Villa 502 - Hot Tub - Bunks - Great View
3 bedrooms, 7 beds, 3.5 bathrooms
12–17 Sept
5.0 out of 5 average rating, 27 reviews
Superhost
Apartment in Winter Park
WP Mountain Retreat • 3BR/2BA • 3 Hot Tubs & Pool
3 bedrooms, 7 beds, 2 bathrooms
12–17 Sept
4.87 out of 5 average rating, 122 reviews
Guest favourite
Cabin in Winter Park
Cabin w/ Deck- Bike & HikeTrails & Downtown- RMNP
5 bedrooms, 5 beds, 3 bathrooms
13–18 Sept
4.86 out of 5 average rating, 21 reviews
Guest favourite
Home in Fraser
New Winter Park Townhouse with Great Views!
4 bedrooms, 5 beds, 3.5 bathrooms
9–14 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Guest suite in Fraser
Madge’s Studio Pets welcome!
1 bedroom, 1 king bed, 1 bathroom
30 Oct – 4 Nov
4.97 out of 5 average rating, 505 reviews
Superhost
Home in Winter Park
Luxury Emerald Escape | Hot Tub | Ski Shuttle
3 bedrooms, 5 beds, 3 bathrooms
9–14 Sept
New place to stay
Top guest favourite
Home in Winter Park
Luxury Winter Park HomeHotTub*Majestic View*Resort
4 bedrooms, 9 beds, 4 bathrooms
13–18 Sept
4.97 out of 5 average rating, 36 reviews
Top guest favourite
Flat in Winter Park
NEW Ski In/Out Condo w/ Hot Tub & Balcony
2 bedrooms, 4 beds, 1 bathroom
12–17 Sept
5.0 out of 5 average rating, 52 reviews
Luxe
Home in Winter Park
Ski In Out Chalet 277 - Hot Tub - Great Views
4 bedrooms, 13 beds, 4.5 bathrooms
13–18 Sept
4.94 out of 5 average rating, 72 reviews
Guest favourite
Apartment in Winter Park
Beautiful Condo at Winter Park!
1 bedroom, 1 bathroom
9–14 Sept
4.94 out of 5 average rating, 105 reviews
Top guest favourite
Apartment in Winter Park
New Condo Downtown Winter Park-Close to the Slopes
2 bedrooms, 6 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 32 reviews
Guest favourite
Townhouse in Winter Park
Luxury Ski in/Ski out town home, private hot tub
4 bedrooms, 5 beds, 4.5 bathrooms
13–18 Sept
4.92 out of 5 average rating, 63 reviews
Top guest favourite
Apartment in Winter Park
Cozy DT condo mins from slopes
2 bedrooms, 3 beds, 2 bathrooms
10–15 Sept
5.0 out of 5 average rating, 106 reviews
Top guest favourite
Home in Fraser
Spacious Cabin with Views • Location • Hot Tub
3 bedrooms, 7 beds, 3.5 bathrooms
9–14 Sept
4.95 out of 5 average rating, 174 reviews
Top guest favourite
Townhouse in Winter Park
Winter Park Townhome w/ Stunning Slope Views!
3 bedrooms, 6 beds, 2.5 bathrooms
14–19 Sept
4.94 out of 5 average rating, 163 reviews
Guest favourite
Apartment in Winter Park
Luxe 4BR Winter Park Retreat w/ Private Hot Tub
4 bedrooms, 5 beds, 3 bathrooms
9–14 Sept
4.91 out of 5 average rating, 67 reviews
Top guest favourite
Apartment in Fraser
Bright Modern Mountain Getaway | Views + Garage
2 bedrooms, 4 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Flat in Winter Park
New Hike or Ski in/out Modern Condo-Quiet w/ Views
2 bedrooms, 4 beds, 1 bathroom
9–14 Sept
5.0 out of 5 average rating, 42 reviews