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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
26–31 Jul
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4.98 out of 5 average rating, 495 reviews
Top guest favourite
Apartment in Winter Park
Downtown Mtn Oasis + Hot Tubs | Steps to Events
2 bedrooms, 5 beds, 3 bathrooms
12–17 Jul
4.96 out of 5 average rating, 107 reviews
Top guest favourite
Flat in Winter Park
Mountain Town Luxury Penthouse
2 bedrooms, 3 beds, 3 bathrooms
21–26 Jul
5.0 out of 5 average rating, 22 reviews
Guest favourite
Home in Winter Park
Luxury Mountain Modern Winter Park Home
4 bedrooms, 9 beds, 4 bathrooms
9–14 Aug
4.97 out of 5 average rating, 29 reviews
Guest favourite
Apartment in Winter Park
WP Mountain Retreat • 3BR/2BA • 3 Hot Tubs & Pool
3 bedrooms, 7 beds, 2 bathrooms
23–28 Jul
4.88 out of 5 average rating, 112 reviews
Top guest favourite
Apartment in Winter Park
Luxury Condo on Main Street - Winter Park, CO
2 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
4.99 out of 5 average rating, 78 reviews
Top guest favourite
Apartment in Winter Park
The Rustic Moose
2 bedrooms, 6 beds, 2 bathrooms
2–7 Aug
5.0 out of 5 average rating, 66 reviews
Guest favourite
Cabin in Winter Park
Cabin w/ Deck- Bike & HikeTrails & Downtown- RMNP
5 bedrooms, 6 beds, 3 bathrooms
26–31 Jul
4.82 out of 5 average rating, 17 reviews
Guest favourite
Apartment in Winter Park
Modern condo w/ hot tub & fireplace
3 bedrooms, 7 beds, 3 bathrooms
2–7 Aug
4.92 out of 5 average rating, 37 reviews
Top guest favourite
Home in Winter Park
WP Resort Villa 502 - Hot Tub - Bunks - Great View
3 bedrooms, 7 beds, 3.5 bathrooms
9–14 Aug
5.0 out of 5 average rating, 22 reviews
Superhost
Home in Winter Park
Downtown WP Loft 106 - Huge Hot Tub - Great Views
3 bedrooms, 8 beds, 2 bathrooms
12–17 Jul
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Winter Park
Downtown WP Villa 165 - Hot Tub - Views - Bunks
4 bedrooms, 7 beds, 5.5 bathrooms
19–24 Jul
Top guest favourite
Home in Winter Park
Winter Park Home | Hot Tub Sauna Walk to Downtown
4 bedrooms, 5 beds, 3.5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 13 reviews
Guest favourite
Townhouse in Winter Park
Cozy Mountain Cabin in the Heart of Winter Park
3 bedrooms, 6 beds, 2.5 bathrooms
31 Aug – 5 Sept
4.82 out of 5 average rating, 185 reviews
Superhost
Home in Winter Park
Downtown WP Loft 57 - Rooftop Hot Tub - Great View
3 bedrooms, 7 beds, 3 bathrooms
26–31 Jul
Guest favourite
Apartment in Winter Park
Amazing Top Floor WP Getaway!
2 bedrooms, 5 beds, 2 bathrooms
12–17 Jul
4.95 out of 5 average rating, 111 reviews
Guest favourite
Flat in Winter Park
Mountain Condo w/ Hot Tub | Walk to Town | Ski Bus
2 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Townhouse in Winter Park
Beautiful Condo at Winter Park!
1 bedroom, 1 bathroom
2–7 Aug
4.94 out of 5 average rating, 100 reviews
Top guest favourite
Townhouse in Winter Park
The Camping Bear
4 bedrooms, 7 beds, 3 bathrooms
7–12 Aug
4.92 out of 5 average rating, 73 reviews