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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
23–28 Aug
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4.98 out of 5 average rating, 497 reviews
Top guest favourite
Guest suite in Fraser
Madge’s Studio Pets welcome!
1 bedroom, 1 king bed, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 500 reviews
Top guest favourite
Flat in Winter Park
Mountain Town Luxury Penthouse
2 bedrooms, 3 beds, 3 bathrooms
14–19 Aug
5.0 out of 5 average rating, 26 reviews
Guest favourite
Apartment in Winter Park
Cozy mountain retreat in downtown Winter Park
1 bedroom, 3 beds, 1 bathroom
13–18 Aug
4.94 out of 5 average rating, 161 reviews
Guest favourite
Apartment in Winter Park
Main Street Luxury - Hot Tub + Trails
1 bedroom, 2 beds, 2 bathrooms
17–22 Aug
4.85 out of 5 average rating, 252 reviews
Flat in Winter Park
The real Winter Park/Alpine experience condo
1 bedroom, 2 beds, 1 bathroom
18–23 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Apartment in Fraser
Updated Fraser Condo | Trails, Shuttle & W/D
1 bedroom, 2 beds, 1 bathroom
31 Aug – 5 Sept
4.98 out of 5 average rating, 171 reviews
Guest favourite
Apartment in Winter Park
One Bdrm Condo Ski In / Ski Out, Hot Tub, Fire Pit
1 bedroom, 2 beds, 1 bathroom
16–21 Aug
4.88 out of 5 average rating, 217 reviews
Top guest favourite
Flat in Winter Park
Mountain Condo w/ Hot Tub | Walk to Town | Ski Bus
2 bedrooms, 4 beds, 2 bathrooms
17–22 Aug
5.0 out of 5 average rating, 15 reviews
Guest favourite
Home in Winter Park
Downtown WP Condo 1409 - Hot Tub - Views - Firepit
2 bedrooms, 4 beds, 2 bathrooms
14–19 Aug
4.94 out of 5 average rating, 31 reviews
Guest favourite
Cabin in Fraser
Cozy Fraser Cabin w/ Views & Moose Sightings!
1 bedroom, 2 queen beds, 1 bathroom
16–21 Aug
4.97 out of 5 average rating, 89 reviews
Guest favourite
Apartment in Winter Park
Walk to Downtown | Hot Tub | Fire place | River |
1 bedroom, 2 beds, 1 bathroom
16–21 Aug
4.88 out of 5 average rating, 344 reviews
Top guest favourite
Cabin in Grand County
Scandinavian-Inspired Escape: Modern Cabin w/ Spa
3 bedrooms, 5 beds, 2 bathrooms
6–11 Sept
4.96 out of 5 average rating, 292 reviews
Top guest favourite
Apartment in Winter Park
Trestle Bike Park•Hot Tub•Pet Friendly•Mtn View
2 beds, 1 bathroom
16–21 Aug
4.94 out of 5 average rating, 34 reviews
Guest favourite
Home in Winter Park
Luxury Winter Park HomeHotTub*Majestic View*Resort
4 bedrooms, 9 beds, 4 bathrooms
16–21 Aug
4.97 out of 5 average rating, 32 reviews
Guest favourite
Apartment in Fraser
Alpine Luxe Loft- Hot Tub, Fireplace, Views, Ski
3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
4.93 out of 5 average rating, 28 reviews
Guest favourite
Home in Winter Park
Downtown WP Cabin 44 - Hot Tub - Views - Bunks
2 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
4.96 out of 5 average rating, 75 reviews
Guest favourite
Apartment in Winter Park
Pool Hot Tub Free Garage · Remodeled Studio
1 bedroom, 4 beds, 1 bathroom
23–28 Aug
4.87 out of 5 average rating, 93 reviews
Top guest favourite
Flat in Winter Park
Modern New build ski in/out. 1br + den.
1 bedroom, 4 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 43 reviews