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Search results; Over 1,000 homes in Winter Park

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Top guest favourite
Townhouse in Winter park
Modern Cabin w/ Hot Tub & Garage - Minutes to Mtn
2 bedrooms, 3 beds, 2 private bathrooms
15–20 Sept
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4.98 out of 5 average rating, 132 reviews
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Superhost
Home in Winter Park
Unbeatable Location Downtown Winter Park W/Hot tub
4 bedrooms, 7 beds, 4.5 bathrooms
1–6 Sept
New place to stay
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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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Flat in Winter Park
The real Winter Park/Alpine experience condo
1 bedroom, 2 beds, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 6 reviews
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Guest favourite
Apartment in Winter Park
One Bdrm Condo Ski In / Ski Out, Hot Tub, Fire Pit
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
4.88 out of 5 average rating, 220 reviews
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Top guest favourite
Home in Winter Park
Hike. Bike. Raft. Rooftop Fire Pit & Hot Tub
5 bedrooms, 8 beds, 7 bathrooms
1–6 Sept
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Apartment in Winter Park
The Rustic Moose
2 bedrooms, 6 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 70 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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Top guest favourite
Apartment in Winter Park
Trestle Bike Park•Hot Tub•Pet Friendly•Mtn View
2 beds, 1 bathroom
7–12 Sept
4.94 out of 5 average rating, 35 reviews
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Top guest favourite
Flat in Winter Park
Beautifully Furnished Modern Condo In Downtown WP
2 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
4.98 out of 5 average rating, 294 reviews
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Guest favourite
Home in Winter Park
Winter Park Pond Chalet 13 - Hot Tub - Views
4 bedrooms, 5 beds, 4 bathrooms
12–17 Sept
4.75 out of 5 average rating, 20 reviews
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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, 33 reviews
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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
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Top guest favourite
Flat in Winter Park
Modern New build ski in/out. 1br + den.
1 bedroom, 4 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 48 reviews
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Guest favourite
Guest suite in Winter Park
New Look! Breakfast, Hot Tub & No Host fee!
1 bedroom, 1 king bed, 1 bathroom
1–6 Sept
4.84 out of 5 average rating, 468 reviews
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Top guest favourite
Apartment in Winter Park
Ski In/Ski Out - Modern Cozy Condo in Winter Park
2 beds, 1 bathroom
20–25 Sept
4.9 out of 5 average rating, 247 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
Home in Winter Park
New Luxury Mountain Home | Hot Tub | 3 Fireplaces
4 bedrooms, 11 beds, 4.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 6 reviews
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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