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Holiday hires in Winter Park

Search and compare Winter Park, CO holiday rentals from hundreds of travel sites on HotelsCombined and save.

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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 ($273). Conversely, the most expensive month to stay in Winter Park is January ($892).

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

The cheapest day to stay in Winter Park is Thursday ($393). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is $646.
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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 9 September 2025. The average price for a hotel in Winter Park is $380/night.
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
$185
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
$254
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
$178
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
$205
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 9 September 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 9 September 2025.

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

    $380 per night is how much a holiday rental in Winter Park costs, on average. $158 per night was the cheapest price recently found by our users, though anything for $309 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 September.

  • 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 $76 and Hotels Under $152. Discover hotel discounts now and make your hotel reservation today.