Vacation rentals in Winter Park
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Travel insights for holiday rentals in Winter Park
Use these up-to-date, data-driven insights about booking a holiday rental in Winter Park including ideal times to book, pricing trends, and more.
What is the cheapest month to book a vacation rental in Winter Park?
The cheapest month to book a vacation rental in Winter Park is June ($165). Conversely, the most expensive month to stay in Winter Park is December ($620).
What is the cheapest day to stay in a vacation rental in Winter Park?
The cheapest day to stay in Winter Park is Sunday ($264). On the other hand, travelers can expect to pay the most on Wednesday, when the average nightly price is $412.
Other accommodations in Winter Park
Find the perfect holiday rental for your stay in Winter Park. There are 1,685 hotels in Winter Park and price data was last updated on 30 April 2025. The average price for a hotel in Winter Park is $302/night.
Show all 1,685 stays
100 Winter Park Drive, Winter Park, CO, United States
1.2 km from city centre
Free Wi-Fi
Parking
$133
Avg. per night
78665 US Highway 40, Winter Park, CO, United States
3.9 km from city centre
Free Wi-Fi
Parking
$152
Avg. per night
670 Winter Park Drive, Winter Park, CO, United States
0.7 km from city centre
Free Wi-Fi
$171
Avg. per night
$176
Avg. per night