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Vacation rentals in Winter Park

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Travel insights for vacation rentals in Winter Park

Use these up-to-date, data-driven insights about booking a vacation 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 (C$ 217). Conversely, the most expensive month to stay in Winter Park is December (C$ 1,026).

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

The cheapest day to stay in Winter Park is Thursday (C$ 220). On the other hand, travelers can expect to pay the most on Wednesday, when the average nightly price is C$ 327.
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Cheapest vacation 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 C$ 197 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 10 November 2025
These Winter Park properties charge the lowest price per night of those we've come across. Prices will typically fluctuate depending on the dates selected, star rating of vacation rental, and vacation rental location.
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
C$ 197
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
C$ 316
Avg. per night
View Deal

Other accommodations in Winter Park

Find the perfect vacation rental for your stay in Winter Park. There are 1,373 hotels in Winter Park and price data was last updated on 10 November 2025. The average price for a hotel in Winter Park is C$ 442/night.
Zephyr Mountain Lodge
Zephyr Mountain Lodge

Zephyr Mountain Lodge

Winter Park, CO, United States
0.7 km from city centre
Air Conditioning
C$ 316
Avg. per night
View Deal
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
C$ 264
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
C$ 236
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
C$ 187
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 US Highway 40, Winter Park, CO, United States
3.4 km from city centre
Free Wi-Fi
Parking
C$ 169
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 10 November 2025.
Utilize the map to find properties close to the Winter Park area(s) or attractions you plan on visiting. More information on a given vacation rental can be accessed by clicking the vacation rental's name within the map.

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 10 November 2025.

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

    Winter Park vacation rentals are C$ 442/night on average. However, you may find that prices fluctuate depending on the time of year. For example, December is the most expensive month to book a vacation rental in Winter Park, and November is often the cheapest month to book. Recently, our users found rentals for C$ 148/night - which is currently the cheapest price. Keep in mind that anything C$ 363/night or less is still considered a good deal.

  • Are there any Motel vacation rentals in Winter Park?

    Yes, there are 2 Motel vacation rentals in Winter Park. According to our data, Valley Hi Motel is currently the most popular Motel rental in the city.

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