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Vacation rentals in Winter Park

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Travel insights for vacation rentals in Winter Park

Use our HotelsCombined data-powered tips to help you find your next vacation rental in Winter Park.

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 ($133). Conversely, the most expensive month to stay in Winter Park is December ($494).

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

The cheapest day to stay in Winter Park is Wednesday ($157). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is $286.
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Other accommodations in Winter Park

Find the perfect vacation rental for your stay in Winter Park. There are 1,847 hotels in Winter Park and price data was last updated on August 20, 2025. The average price for a hotel in Winter Park is $253/night.
Zephyr Mountain Lodge
Zephyr Mountain Lodge

Zephyr Mountain Lodge

Winter Park, CO, United States
0.4 mi from city centre
Air Conditioning
$166
Avg. per night
View Deal
Valley Hi Motel
Valley Hi Motel

Valley Hi Motel

79025 US Highway 40, Winter Park, CO, United States
2.0 mi from city centre
Free Wi-Fi
Parking
$133
Avg. per night
View Deal

Where to stay in Winter Park

Explore different neighborhoods and areas within Winter Park to find the perfect location for your stay. Map data was last updated on August 20, 2025.
Scroll through the map to find vacation rentals close to the Winter Park neighborhood(s) you plan on visiting. As an added benefit, users can click a vacation rental they're interesting in to find helpful information and deals for that vacation 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 August 20, 2025.

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

    $254 per night is how much a vacation rental in Winter Park costs, on average. $104 per night was the cheapest price recently found by our users, though anything for $222 per night or less is a good deal. Keep in mind that Winter Park vacation rental prices fluctuate throughout the year: the most expensive month to book is December, and the cheapest time to book is September.

  • Are there any Motel vacation rentals in Winter Park?

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

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