Insights
Cheapest hotels
Where to stay

Vacation rentals in Winter Park

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

...and more

Learn why travellers love HotelsCombined

Compare hotel ratings collected from thousands of user reviews.

One search gives you accurate pricing on affordable hotels.

Customize your results by hotel chain, amenities, price, and more.

Search for hotels as many times as you want – for free.

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 day to stay in a vacation rental in Winter Park?

The cheapest day to stay in Winter Park is Thursday (C$ 361). On the other hand, travelers can expect to pay the most on Sunday, when the average nightly price is C$ 701.

Find deals

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$ 195 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 15 January 2026
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$ 195
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$ 464
Avg. per night
View Deal

Other accommodations in Winter Park

Find the perfect vacation rental for your stay in Winter Park. There are 1,346 hotels in Winter Park and price data was last updated on 15 January 2026. The average price for a hotel in Winter Park is .
Zephyr Mountain Lodge
Zephyr Mountain Lodge

Zephyr Mountain Lodge

Winter Park, CO, United States
0.7 km from city centre
Air Conditioning
C$ 464
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$ 318
Avg. per night
View Deal
Valley Hi Hotel
Valley Hi Hotel

Valley Hi Hotel

79025 US Highway 40, Winter Park, CO, United States
3.3 km from city centre
Free Wi-Fi
Parking
C$ 235
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$ 229
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 15 January 2026.
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 15 January 2026.

  • 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$ 147/night - which is currently the cheapest price. Keep in mind that anything C$ 385/night or less is still considered a good deal.

Find better results for your stay in Winter Park