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Holiday hires 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 ($188). Conversely, the most expensive month to stay in Winter Park is December ($995).

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

The cheapest day to stay in Winter Park is Thursday ($242). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is $356.
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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 $215 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 24 10월 2025
At the moment, these holiday rentals offer the lowest nightly rate out of those we've come across in Winter Park. 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
$215
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
$249
Avg. per night
View Deal

Other accommodations in Winter Park

Find the perfect holiday rental for your stay in Winter Park. There are 1,393 hotels in Winter Park and price data was last updated on 24 10월 2025. The average price for a hotel in Winter Park is $463/night.
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
$263
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
$249
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
$197
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 24 10월 2025.
Whether you're visiting Winter Park for leisure or business, utilise the map to find holiday rentals close to your ideal location. You can find more information on a particular holiday rental within the map by clicking on its name.

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 24 10월 2025.

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

    $463 per night is how much a holiday rental in Winter Park costs, on average. $162 per night was the cheapest price recently found by our users, though anything for $371 per night or less is a good deal. Keep in mind that Winter Park holiday rental prices fluctuate throughout the year: the most expensive month to book is January, and the cheapest time to book is November.

  • Are there any Motel holiday rentals in Winter Park?

    If you’re looking to book a Motel holiday rental in Winter Park, then you have 2 to choose from. We recommend looking at Valley Hi Motel as it’s currently the most popular Motel rental among our users.

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Search cheap hotels with HotelsCombined. Use the hotel finder to search for the cheapest hotel deal for all major destinations around the world. HotelsCombined searches hundreds of hotel booking sites to help you find hotels and book the ones that suit you best. Since HotelsCombined searches many hotel sites at once, you can find discounted hotels quickly, including Hotels Under $77 and Hotels Under $154. Discover hotel discounts now and make your hotel reservation today.