Vacation 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 (S$ 219). Conversely, the most expensive month to stay in Winter Park is December (S$ 812).

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

The cheapest day to stay in Winter Park is Wednesday (S$ 248). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is S$ 455.

Other accommodations in Winter Park

Find the perfect holiday rental for your stay in Winter Park. There are 1,824 hotels in Winter Park and price data was last updated on 15 August 2025. The average price for a hotel in Winter Park is S$ 322/night.
Winter Park, CO, United States
0.7 km from city centre
Air conditioning
S$ 209
Avg. per night
79025 US Highway 40, Winter Park, CO, United States
3.3 km from city centre
Free Wi-Fi
Parking
S$ 171
Avg. per night
817 County Road 834, Winter Park, CO, United States
6.3 km from city centre
Free Wi-Fi
S$ 191
Avg. per night

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 15 August 2025.
Navigate to the areas in Winter Park you plan to visit to find vacation rentals that are close by. You can find more information on a particular vacation 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 15 August 2025.
  • How much does a holiday rental in Winter Park cost?

    On average, it costs S$ 323 per night for a Winter Park holiday rental, but S$ 280 per night or less would be considered a good deal. The cheapest holiday rental price our users have found recently in Winter Park was for S$ 134 per night. If you can, try to avoid booking your rental December (as this is the most expensive month). Booking September (the cheapest month) may end up saving you money.

  • Are there any Motel holiday rentals in Winter Park?

    There are 2 holiday rentals in Winter Park that fall under the Motel category, the most popular is Valley Hi Motel.

Find better results for your stay in Winter Park

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