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Search results; Over 1,000 homes in Winter Park

Guest favourite
Boutique hotel in Winter Park
Winter Park Chateau: Mountain Goat + Llama Loft
1 bedroom, 3 beds, 1 private bathroom
7–12 Sept
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5.0 out of 5 average rating, 8 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
Guest suite in Fraser
The Mountains are calling!
1 queen bed, 1 bathroom
13–18 Sept
4.92 out of 5 average rating, 702 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
Home in Winter Park
Chalet Apres | Amazing Location | Hot Tub & Sauna
2 bedrooms, 3 beds, 2 bathrooms
6–11 Sept
4.75 out of 5 average rating, 24 reviews
Guest favourite
Apartment in Winter Park
Winter Park Ski Resort - Top Floor
1 bedroom, 1 sofa bed, 1 bathroom
12–17 Sept
4.98 out of 5 average rating, 40 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, 502 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
Cabin in Winter Park
Cozy Cabin in Perfect Location
2 beds, 1 bathroom
7–12 Oct
4.84 out of 5 average rating, 653 reviews
Guest favourite
Apartment in Fraser
Mountain Retreat | Private Hot Tub | Sleeps Eight
2 bedrooms, 4 beds, 2 bathrooms
6–11 Sept
4.92 out of 5 average rating, 13 reviews
Guest favourite
Apartment in Fraser
Spacious Family Friendly Townhome Retreat
3 bedrooms, 6 beds, 3.5 bathrooms
6–11 Sept
4.97 out of 5 average rating, 30 reviews
Luxe
Home in Winter Park
Ski In Out Chalet 277 - Hot Tub - Great Views
4 bedrooms, 13 beds, 4.5 bathrooms
6–11 Sept
4.94 out of 5 average rating, 72 reviews
Top guest favourite
Apartment in Winter Park
Cozy DT condo mins from slopes
2 bedrooms, 3 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 105 reviews
Top guest favourite
Apartment in Winter Park
Downtown Mtn Oasis + Hot Tubs | Steps to Events
2 bedrooms, 5 beds, 3 bathrooms
7–12 Sept
4.96 out of 5 average rating, 114 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
Guest favourite
Flat in Winter Park
1BR Condo in Winter Park, CO
1 bedroom, 2 beds, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 50 reviews
Top guest favourite
Apartment in Winter Park
The Rustic Moose
2 bedrooms, 6 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 70 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
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