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Search results; Over 1,000 homes in Winter Park

Guest favourite
Apartment in Winter Park
Homebase Snowblaze
Studio, 2 beds, 1 private bathroom
13–18 Sept
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4.88 out of 5 average rating, 259 reviews
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, 35 reviews
Top guest favourite
Apartment in Winter Park
Luxury Condo on Main Street - Winter Park, CO
2 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
4.99 out of 5 average rating, 81 reviews
Guest favourite
Townhouse in Winter Park
Luxury Winter Park Retreat with Private Hot Tub
3 bedrooms, 4 beds, 4 bathrooms
20–25 Sept
4.97 out of 5 average rating, 34 reviews
Guest favourite
Townhouse in Winter Park
Modern/Rustic 2-bedroom Townhouse + Bonus Loft
2 bedrooms, 3 beds, 2 bathrooms
22–27 Sept
4.97 out of 5 average rating, 201 reviews
Top guest favourite
Townhouse in Winter Park
The Camping Bear
4 bedrooms, 7 beds, 3 bathrooms
14–19 Sept
4.92 out of 5 average rating, 78 reviews
Superhost
Townhouse in Winter Park
Spacious Mountain Townhome | Private Hot Tub
3 bedrooms, 5 beds, 3 bathrooms
17–22 Sept
4.9 out of 5 average rating, 185 reviews
Guest favourite
Apartment in Winter Park
Winter Park Condo w/ Fireplace - 4 Mi to Slopes!
2 bedrooms, 4 beds, 2 bathrooms
6–11 Sept
4.95 out of 5 average rating, 165 reviews
Top guest favourite
Apartment in Fraser
Walk to Restaurants! Hike, Bike and Fish this Fall
1 bedroom, 3 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 147 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
Superhost
Apartment in Fraser
Meadow Ridge Retreat | Near Winter Park
2 bedrooms, 2 beds, 1 bathroom
12–17 Sept
New place to stay
Top guest favourite
Apartment in Winter Park
New Condo Downtown Winter Park-Close to the Slopes
2 bedrooms, 6 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 32 reviews
Guest favourite
Apartment in Fraser
Alpine Luxe Loft- Hot Tub, Fireplace, Views, Ski
3 bedrooms, 4 beds, 2 bathrooms
30 Oct – 4 Nov
4.91 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
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, 51 reviews
Top guest favourite
Home in Fraser
Mountain Retreat | New Condo | Private Hot Tub
2 bedrooms, 4 beds, 2 bathrooms
16–21 Sept
4.97 out of 5 average rating, 86 reviews
Superhost
Apartment in Winter Park
Summer Escape • Riverfront Stay in WP
2 bedrooms, 4 beds, 3 bathrooms
7–12 Sept
4.82 out of 5 average rating, 11 reviews
Guest favourite
Home in Winter Park
Downtown WP Penthouse 221 I Private Hot Tub I View
3 bedrooms, 7 beds, 3 bathrooms
13–18 Sept
4.9 out of 5 average rating, 10 reviews
Superhost
Home in Winter Park
Unbeatable Location Downtown Winter Park W/Hot tub
4 bedrooms, 7 beds, 4.5 bathrooms
6–11 Sept
New place to stay