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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 ($340). Conversely, the most expensive month to stay in Winter Park is January ($1,112).

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

The cheapest day to stay in Winter Park is Thursday ($490). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is $805.
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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 $424/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
$229
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
$207
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
$285
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
$198
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.
Navigate to the areas in Winter Park you plan to visit to find holiday rentals that are close by. As an added benefit, users can click a holiday rental they're interesting in to find helpful information and deals for that holiday rental.

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?

    $424/night is a typical cost for a holiday rental in Winter Park throughout the year. Rental prices do vary though, and you’ll find that January is the most expensive month to book, and September is the cheapest month to book. HotelsCombined users recently found Winter Park holiday rentals for as low as $177/night. In general, any Winter Park rental for $345 or less is a good deal.

  • Are there any Motel holiday rentals in Winter Park?

    At the moment, there are 2 properties listed as a Motel holiday rental in Winter Park. A popular Motel in Winter Park amongst our users is Valley Hi Motel.

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