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Search results; Over 1,000 homes in Winter Park

Top guest favourite
Guest suite in Winter Park
Charming Suite in Old Town Winter Park
1 bedroom, 1 bed, 1 private bathroom
7–12 Sept
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4.98 out of 5 average rating, 498 reviews
Guest favourite
Home in Winter Park
WP Resort Villa 402 - Hot Tub - Arcade - Views
3 bedrooms, 8 beds, 3.5 bathrooms
7–12 Sept
4.85 out of 5 average rating, 40 reviews
Luxe
Home in Winter Park
Cast. Summit. Pedal. Soak. Winter Park Luxury
5 bedrooms, 8 beds, 5.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 11 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
Top guest favourite
Home in Fraser
Spacious Cabin with Views • Location • Hot Tub
3 bedrooms, 7 beds, 3.5 bathrooms
7–12 Sept
4.95 out of 5 average rating, 174 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
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, 26 reviews
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, 220 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
Guest favourite
Apartment in Winter Park
Close to everything, AC in Downtown with Views!
2 bedrooms, 3 beds, 2.5 bathrooms
7–12 Sept
4.92 out of 5 average rating, 12 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
Home in Fraser
Spruce Ridge Villa 714H - Great Views - Bunk Room
3 bedrooms, 5 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Flat in Winter Park
Hip mountain pad • Steps to Summer Festivals
2 beds, 1 bathroom
20–25 Sept
4.85 out of 5 average rating, 39 reviews
Top guest favourite
Flat in Winter Park
Modern New build ski in/out. 1br + den.
1 bedroom, 4 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 48 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
Top guest favourite
Apartment in Winter Park
Ski In/Out Sleep 10 LUX ZML Penthouse Low Chemical
3 bedrooms, 7 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Apartment in Winter Park
Cozy Winter Park Riverfront Studio~ Walk Downtown
2 beds, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 121 reviews
Guest favourite
Flat in Winter Park
Downtown Winter Park W/ Hot Tub
1 bedroom, 3 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 20 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