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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 November (S$ 224). Conversely, the most expensive month to stay in Winter Park is December (S$ 668).

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$ 264). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is S$ 403.
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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$ 193 per night. There is currently one property in Winter Park that can be booked for this price. Zephyr Mountain Lodge is one of the hotels that can be booked for the lowest price in Winter Park. Price data was last updated on 18 September 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.
Zephyr Mountain Lodge
Zephyr Mountain Lodge

Zephyr Mountain Lodge

Winter Park, CO, United States
0.7 km from city centre
Air conditioning
S$ 193
Avg. per night
View Deal

Other accommodations in Winter Park

Find the perfect holiday rental for your stay in Winter Park. There are 1,804 hotels in Winter Park and price data was last updated on 18 September 2025. The average price for a hotel in Winter Park is S$ 332/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
S$ 226
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$ 172
Avg. per night
View Deal
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
S$ 168
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
S$ 170
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
S$ 151
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 18 September 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 18 September 2025.

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

    On average, it costs S$ 332 per night for a Winter Park holiday rental, but S$ 252 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$ 135 per night. If you can, try to avoid booking your rental January (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.

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