How much does a holiday rental in Winter Park cost?

The average cost for a holiday rental in Winter Park is $320/night. A good holiday rental deal in Winter Park would be for $283/night or less. The cheapest rental deal found recently by our users was $105/night. If you’re flexible with your travel dates, then try to avoid booking December, the most expensive month of the year. Booking November is the cheapest month to book a holiday rental in Winter Park.

Winter Park Holiday Rentals, Apartments & Condos

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 day to stay in a vacation rental in Winter Park?

The cheapest day to stay in Winter Park is Monday ($207). On the other hand, travelers can expect to pay the most on Tuesday, when the average nightly price is $444.

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Cheapest holiday rentals in Winter Park, Colorado

For those on a budget, these are the cheapest vacation rentals available in Winter Park for the selected dates. Prices can differ depending on the dates selected, so use the search form to browse more options if you have flexibility.

Show all 1,346 holiday rentals

Winter Park Mountain Lodge

81699 Us Highway 40, Winter Park, CO, United States

0.7 km from city centre

Pool

Free Wi-Fi

Parking

$140

Avg. per night

View Deal

Zephyr Mountain Lodge

Winter Park, CO, United States

0.7 km from city centre

Air conditioning

$289

Avg. per night

View Deal

Other accommodations in Winter Park

Show all 1,346 stays

Valley Hi Motel

79025 US Highway 40, Winter Park, CO, United States

3.3 km from city centre

Free Wi-Fi

Parking

$162

Avg. per night

View Deal

The Vintage Hotel

100 Winter Park Drive, Winter Park, CO, United States

1.2 km from city centre

Free Wi-Fi

Parking

$162

Avg. per night

View Deal

Timber Run Vista 2

145 Forest Trail, Unit 2, Winter Park, CO, United States

3.7 km from city centre

Free Wi-Fi

$110

Avg. per night

View Deal

Indian Peaks Resort

817 County Road 834, Winter Park, CO, United States

6.3 km from city centre

Free Wi-Fi

$211

Avg. per night

View Deal

Where to stay in Winter Park

Utilize the map to find properties close to the Winter Park area(s) or attractions you plan on visiting. Clicking on a vacation rental name will take you to a page with pricing, reviews, and more useful information.

Facts about staying in Winter Park

How much does a holiday rental in Winter Park cost?
The average cost for a holiday rental in Winter Park is $320/night. A good holiday rental deal in Winter Park would be for $283/night or less. The cheapest rental deal found recently by our users was $105/night. If you’re flexible with your travel dates, then try to avoid booking December, the most expensive month of the year. Booking November is the cheapest month to book a holiday rental in Winter Park.

Travel insights for holiday rentals in Winter Park

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

The cheapest day to stay in Winter Park is Monday ($207). On the other hand, travelers can expect to pay the most on Tuesday, when the average nightly price is $444.

Cheapest holiday rentals in Winter Park, Colorado

For those on a budget, these are the cheapest vacation rentals available in Winter Park for the selected dates. Prices can differ depending on the dates selected, so use the search form to browse more options if you have flexibility.

Other accommodations in Winter Park

Find the perfect holiday rental for your stay in Winter Park. There are 1,346 hotels in Winter Park and price data was last updated on 30 January 2026. The average price for a hotel in Winter Park is .

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 January 2026.

Utilize the map to find properties close to the Winter Park area(s) or attractions you plan on visiting. Clicking on a vacation rental name will take you to a page with pricing, reviews, and more useful information.

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 January 2026.

How much does a holiday rental in Winter Park cost?

Find better results for your stay in Winter Park

Popular holiday destinations in Colorado

Find holiday rentals in popular Colorado cities that fit your unique needs

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Vacation rentals in Winter Park

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

Travel insights for holiday rentals in Winter Park

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

The cheapest day to stay in Winter Park is Monday ($207). On the other hand, travelers can expect to pay the most on Tuesday, when the average nightly price is $444.

Cheapest holiday rentals in Winter Park, Colorado

For those on a budget, these are the cheapest vacation rentals available in Winter Park for the selected dates. Prices can differ depending on the dates selected, so use the search form to browse more options if you have flexibility.

Other accommodations in Winter Park

Find the perfect holiday rental for your stay in Winter Park. There are 1,346 hotels in Winter Park and price data was last updated on 30 January 2026. The average price for a hotel in Winter Park is .

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 January 2026.

Utilize the map to find properties close to the Winter Park area(s) or attractions you plan on visiting. Clicking on a vacation rental name will take you to a page with pricing, reviews, and more useful information.

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 January 2026.

How much does a holiday rental in Winter Park cost?

Find better results for your stay in Winter Park

Popular holiday destinations in Colorado

Find holiday rentals in popular Colorado cities that fit your unique needs