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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 May (S$ 200). Conversely, the most expensive month to stay in Winter Park is December (S$ 841).

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

The cheapest day to stay in Winter Park is Thursday (S$ 205). On the other hand, travelers can expect to pay the most on Wednesday, when the average nightly price is S$ 284.
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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 S$ 182 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 30 octobre 2025
Out of the vacation rentals in Winter Park we've come across, these properties are priced the lowest. Consider alternative dates if you're able 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
S$ 182
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
S$ 216
Avg. per night
View Deal

Other accommodations in Winter Park

Find the perfect holiday rental for your stay in Winter Park. There are 1,375 hotels in Winter Park and price data was last updated on 30 octobre 2025. The average price for a hotel in Winter Park is S$ 417/night.
Zephyr Mountain Lodge
Zephyr Mountain Lodge

Zephyr Mountain Lodge

Winter Park, CO, United States
0.7 km from city centre
Air conditioning
S$ 216
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
S$ 161
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 30 octobre 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 30 octobre 2025.

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

    On average, it costs S$ 418 per night for a Winter Park holiday rental, but S$ 348 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$ 137 per night. If you can, try to avoid booking your rental January (as this is the most expensive month). Booking November (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.

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