Holiday houses in Winter Park
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Top-rated holiday rentals in Winter Park
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Winter Park holiday rentals
Other great holiday rentals in Winter Park
Guest favourite
Condo in Winter Park
4.93 out of 5 average rating, 171 reviewsMountain retreat | Top Floor | WP Base Village
Guest favourite
Apartment in Winter Park
4.81 out of 5 average rating, 124 reviewsLovely one bedroom Apartment in an Aspen forest.
Guest favourite
Condo in Fraser
4.9 out of 5 average rating, 134 reviewsComfortable Mountain Retreat
Superhost
Condo in Winter Park
4.78 out of 5 average rating, 306 reviewsBeautiful Cozy Studio at the Base-Heated Parking
Guest favourite
Condo in Winter Park
4.93 out of 5 average rating, 115 reviewsMinutes from the lifts, seconds from the hot tub.
Guest favourite
Apartment in Winter Park
4.93 out of 5 average rating, 30 reviewsSki-in/Ski-out Studio in WP!
Guest favourite
Condo in Winter Park
5.0 out of 5 average rating, 31 reviewsSki in Ski Out Cozy Condo
Guest favourite
Condo in Winter Park
4.83 out of 5 average rating, 65 reviewsPrime location, amazing views, stylish, sleeps 7
Quick stats about holiday rentals in Winter Park
Total rentals
1.4K properties
Rentals with a pool
570 properties have a pool
Pet-friendly rentals
190 properties allow pets
Family-friendly rentals
1K properties are a good fit for families
Total number of reviews
37K reviews
Nightly prices starting at
$83 NZD before taxes and fees
Destinations to explore
- Aspen Holiday rentals
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- Apartment rentals Winter Park
- Rentals with a fire pit Winter Park
- Rentals with a patio Winter Park
- Rentals with an EV charger Winter Park
- Cabin rentals Winter Park
- Rentals with a fireplace Winter Park
- Rentals with pools Winter Park
- Kid-friendly rentals Winter Park
- Condo rentals Winter Park
- Rentals with a hot tub Winter Park
- Pet-friendly rentals Winter Park
- Family-friendly rentals Winter Park
- Rentals with a sauna Winter Park
- House rentals Winter Park
- Rentals with a kayak Winter Park
- Rentals with lake access Winter Park
- Rentals with outdoor seating Winter Park
- Fitness-friendly rentals Winter Park
- Ski-in/ski-out rentals Winter Park
- Townhouse rentals Winter Park
- Waterfront rentals Winter Park
- Rentals with a washing machine and dryer Winter Park
- Monthly Rentals Winter Park
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