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Search results; Over 1,000 homes in Winter Park

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Guest favourite
Apartment in Winter Park
10 Minute Walk to the Winter Park Gondola 6 beds.
3 bedrooms, 6 beds, 2.5 private bathrooms
15–20 Oct
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4.94 out of 5 average rating, 69 reviews
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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, 34 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
12–17 Sept
4.87 out of 5 average rating, 122 reviews
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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
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Apartment in Fraser
WP Shuttle | Condo in Downtown Fraser
2 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Cabin in Winter Park
Cabin w/ Deck- Bike & HikeTrails & Downtown- RMNP
5 bedrooms, 5 beds, 3 bathrooms
6–11 Sept
4.86 out of 5 average rating, 21 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
12–17 Sept
5.0 out of 5 average rating, 26 reviews
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Superhost
Home in Winter Park
Downtown WP Villa 165 - Hot Tub - Views - Bunks
4 bedrooms, 7 beds, 5.5 bathrooms
7–12 Sept
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Flat in Winter Park
The real Winter Park/Alpine experience condo
1 bedroom, 2 beds, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 4 reviews
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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
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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, 13 reviews
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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
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Top guest favourite
Apartment in Fraser
Bright Modern Mountain Getaway | Views + Garage
2 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 49 reviews
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Top guest favourite
Flat in Winter Park
Hip mountain pad • Steps to Summer Festivals
2 beds, 1 bathroom
28 Sept – 4 Oct
4.84 out of 5 average rating, 38 reviews
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Superhost
Home in Winter Park
Ramble Retreat I Downtown Winter Park w/Hot Tub
4 bedrooms, 7 beds, 4.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 3 reviews
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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
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Guest favourite
Apartment in Winter Park
Prime location, amazing views, stylish, sleeps 7
2 bedrooms, 5 beds, 2 bathrooms
8–13 Sept
4.86 out of 5 average rating, 117 reviews
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Superhost
Townhouse in Winter Park
Beautiful Condo at Winter Park!
1 bedroom, 1 bathroom
8–13 Sept
4.94 out of 5 average rating, 105 reviews
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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, 501 reviews