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Vacation rentals in Winter Park

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Travel insights for vacation rentals in Winter Park

Use these up-to-date, data-driven insights about booking a vacation 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 November (C$ 224). Conversely, the most expensive month to stay in Winter Park is January (C$ 732).

What is the cheapest day to stay in a vacation rental in Winter Park?

The cheapest day to stay in Winter Park is Wednesday (C$ 342). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is C$ 530.
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Other accommodations in Winter Park

Find the perfect vacation rental for your stay in Winter Park. There are 1,843 hotels in Winter Park and price data was last updated on 28 August 2025. The average price for a hotel in Winter Park is C$ 345/night.
The Vintage Hotel
The Vintage Hotel

The Vintage Hotel

100 Winter Park Drive, Winter Park, CO, United States
1.2 km from city centre
Free Wi-Fi
Parking
C$ 158
Avg. per night
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Winter Park Chateau
Winter Park Chateau

Winter Park Chateau

405 Lions Gate Drive, Winter Park, CO, United States
4.1 km from city centre
Free Wi-Fi
Parking
C$ 242
Avg. per night
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The Viking Lodge - Downtown Winter Park Colorado
The Viking Lodge - Downtown Winter Park Colorado

The Viking Lodge - Downtown Winter Park Colorado

78966 Main Street, Winter Park, CO, United States
3.4 km from city centre
Free Wi-Fi
Parking
C$ 163
Avg. per night
View Deal
Valley Hi Motel
Valley Hi Motel

Valley Hi Motel

79025 US Highway 40, Winter Park, CO, United States
3.3 km from city centre
Free Wi-Fi
Parking
C$ 186
Avg. per night
View Deal

Where to stay in Winter Park

Explore different neighbourhoods and areas within Winter Park to find the perfect location for your stay. Map data was last updated on 28 August 2025.
Utilize the map to find properties close to the Winter Park area(s) or attractions you plan on visiting. More information on a given vacation rental can be accessed by clicking the vacation rental's name within the map.

Facts about staying in Winter Park

Find useful tips and insights about staying in Winter Park to help you make the most of your experience. FAQs were last updated on 28 August 2025.

  • How much does a vacation rental in Winter Park cost?

    Winter Park vacation rentals are C$ 346/night on average. However, you may find that prices fluctuate depending on the time of year. For example, January is the most expensive month to book a vacation rental in Winter Park, and September is often the cheapest month to book. Recently, our users found rentals for C$ 144/night - which is currently the cheapest price. Keep in mind that anything C$ 282/night or less is still considered a good deal.

  • Are there any Motel vacation rentals in Winter Park?

    Yes, there are 2 Motel vacation rentals in Winter Park. According to our data, Valley Hi Motel is currently the most popular Motel rental in the city.

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