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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 October ($293). Conversely, the most expensive month to stay in Winter Park is December ($1,031).

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

The cheapest day to stay in Winter Park is Monday ($353). On the other hand, travelers can expect to pay the most on Saturday, when the average nightly price is $710.

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Cheapest holiday rentals in Winter Park, Colorado

Discover affordable stays in Winter Park that provide a quality experience without breaking the bank. Hotels in Winter Park can be found for as low as $238 per night. There is currently one property in Winter Park that can be booked for this price. Winter Park Mountain Lodge is one of the hotels that can be booked for the lowest price in Winter Park. Price data was last updated on 23 January 2026
These Winter Park properties charge the lowest price per night of those we've come across. If you have the flexibility, change the dates selected to compare prices.
Winter Park Mountain Lodge
Winter Park Mountain Lodge

Winter Park Mountain Lodge

81699 Us Highway 40, Winter Park, CO, United States
0.7 km from city centre
Pool
Free Wi-Fi
Parking
$238
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
$551
Avg. per night
View Deal

Other accommodations in Winter Park

Find the perfect holiday rental for your stay in Winter Park. There are 1,347 hotels in Winter Park and price data was last updated on 23 January 2026. The average price for a hotel in Winter Park is $547/night.
Zephyr Mountain Lodge
Zephyr Mountain Lodge

Zephyr Mountain Lodge

Winter Park, CO, United States
0.7 km from city centre
Air conditioning
$551
Avg. per night
View Deal
Indian Peaks Resort
Indian Peaks Resort

Indian Peaks Resort

817 County Road 834, Winter Park, CO, United States
6.3 km from city centre
Free Wi-Fi
$384
Avg. per night
View Deal
Valley Hi Hotel
Valley Hi Hotel

Valley Hi Hotel

79025 US Highway 40, Winter Park, CO, United States
3.3 km from city centre
Free Wi-Fi
Parking
$282
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 23 January 2026.
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 23 January 2026.

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

    $548/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 December is the most expensive month to book, and November is the cheapest month to book. HotelsCombined users recently found Winter Park holiday rentals for as low as $179/night. In general, any Winter Park rental for $489 or less is a good deal.

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