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Holiday 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 November (€86). Conversely, the most expensive month to stay in Winter Park is January (€281).

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

The cheapest day to stay in Winter Park is Thursday (€124). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is €204.
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Other accommodations in Winter Park

Find the perfect holiday rental for your stay in Winter Park. There are 1,830 hotels in Winter Park and price data was last updated on 8 September 2025. The average price for a hotel in Winter Park is €213/night.
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
€115
Avg. per night
View Deal
Zephyr Mountain Lodge
Zephyr Mountain Lodge

Zephyr Mountain Lodge

Winter Park, CO, United States
0.7 km from city centre
Air conditioning
€142
Avg. per night
View Deal
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
€104
Avg. per night
View Deal
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
€143
Avg. per night
View Deal
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
€100
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 8 September 2025.
Whether you're visiting Winter Park for leisure or business, utilise the map to find holiday rentals close to your ideal location. Clicking on a holiday rental name will take you to a page with pricing, reviews, and more useful information.

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 8 September 2025.

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

    The average cost for a holiday rental in Winter Park is €214/night. A good holiday rental deal in Winter Park would be for €173/night or less. The cheapest rental deal found recently by our users was €89/night. If you’re flexible with your travel dates, then try to avoid booking January, the most expensive month of the year. Booking September is the cheapest month to book a holiday rental in Winter Park.

  • Are there any Motel holiday rentals in Winter Park?

    There are 2 holiday rentals in Winter Park that fall under the Motel category, the most popular is Valley Hi Motel.

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