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Search results; Over 1,000 homes in Winter Park

Top guest favourite
Apartment in Winter Park
Cozy Condo in Forest + Walk to Town!
2 bedrooms, 6 beds, 2 private bathrooms
1–6 Aug
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4.96 out of 5 average rating, 104 reviews
Superhost
Home in Winter Park
Brand New! I Downtown Winter Park w/Hot Tub
4 bedrooms, 4 beds
13–18 Aug
New place to stay
Top guest favourite
Townhouse in Winter Park
Luxury Winter Park Retreat with Private Hot Tub
3 bedrooms, 4 beds
2–7 Aug
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Home in Fraser
Spruce Ridge Villa 714H - Great Views - Bunk Room
3 bedrooms, 5 beds
17–22 Aug
5.0 out of 5 average rating, 9 reviews
Luxe
Home in Tabernash
Pole Creek Home 739 - Hot Tub - Views - Game Room
5 bedrooms, 9 beds
16–21 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Winter Park
WP Resort Villa 502 - Hot Tub - Bunks - Great View
3 bedrooms, 7 beds
9–14 Aug
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Home in Winter Park
Duplex In town! Views! PrvtHottub,2Cgarage,Sleeps9
3 bedrooms, 6 beds
1–6 Aug
5.0 out of 5 average rating, 18 reviews
Superhost
Home in Fraser
Mountain Villa 1064 - Private Hot Tub - Views
3 bedrooms, 5 beds
2–7 Aug
New place to stay
Guest favourite
Apartment in Winter Park
Modern condo w/ hot tub & fireplace
3 bedrooms, 7 beds
2–7 Aug
4.92 out of 5 average rating, 37 reviews
Guest favourite
Flat in Winter Park
Into the Ultimate Summer & Endless Discovery
2 bedrooms, 3 beds
2–7 Aug
5.0 out of 5 average rating, 22 reviews
Guest favourite
Home in Winter Park
Chateau Louise • Group & Family Friendly • Central
3 bedrooms, 5 beds
1–6 Aug
5.0 out of 5 average rating, 9 reviews
Guest favourite
Flat in Fraser
Eagle Ridge above the summit
2 bedrooms, 3 beds
1–6 Aug
5.0 out of 5 average rating, 11 reviews
Home in Fraser
New Winter Park Townhouse with Great Views!
4 bedrooms, 5 beds
2–7 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Winter Park
Downtown WP Condo 2203 - Hot Tub - Views - Firepit
2 bedrooms, 2 beds
2–7 Aug
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Flat in Winter Park
Mountain Town Luxury Penthouse
2 bedrooms, 3 beds
11–16 Aug
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Townhouse in Winter park
Modern Cabin w/ Hot Tub & Garage - Minutes to Mtn
2 bedrooms, 3 king beds
4–9 Aug
4.98 out of 5 average rating, 132 reviews
Guest favourite
Home in Fraser
Downtown WP Chalet 111 - Hot Tub - Views - Bunks
3 bedrooms, 4 beds
9–14 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Apartment in Fraser
Luxury Condo w Private Hot Tub - Fraser, CO
2 bedrooms, 3 beds
28 Aug – 2 Sept
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Cabin in Grand County
Scandinavian-Inspired Escape: Modern Cabin w/ Spa
3 bedrooms, 5 beds
28 Aug – 2 Sept
4.96 out of 5 average rating, 290 reviews