Winter Park Vacation Rentals

Compare 2,202 available properties from 19 providers
Winter Park
Save up to 49%

Best Vacation Home Deals in Winter Park

-49%
e.g. 9/29 - 10/6
Condo ∙ 4 guests ∙ 1 bedroom
Winter Park, Grand County, Colorado, United States
from $157 $308
RedAwning
4.8
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-45%
e.g. 5/4 - 5/11
Condo ∙ 2 guests
Winter Park, Grand County, Colorado, United States
from $214 $384
RedAwning
5.0
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-44%
e.g. 10/6 - 10/13
Condo ∙ 4 guests ∙ 1 bedroom
Winter Park, Grand County, Colorado, United States
from $183 $329
RedAwning
4.0
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Compare and find a vacation rental that fits your needs among the 2,202 fantastic rentals from several partner websites in Winter Park. Every one of the offers from our partner websites are instantaneously compared on our website, allowing you to save up to 49%.

Recommended Vacation Rentals in Winter Park

Rent a vacation accommodation in Winter Park: from $69 per night

Apartment ∙ 4 guests ∙ 1 bedroom
Winter Park, Grand County, Colorado, United States
from $130
VRBO
4.6
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Apartment ∙ 4 guests
Winter Park, Grand County, Colorado, United States
from $351
VRBO
5.0
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Apartment ∙ 4 guests ∙ 1 bedroom
Winter Park, Grand County, Colorado, United States
from $408
VRBO
5.0
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House ∙ 2 guests
Winter Park, Grand County, Colorado, United States
from $129
VRBO
5.0
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Apartment ∙ 4 guests ∙ 1 bedroom
Winter Park, Grand County, Colorado, United States
from $255
VRBO
4.7
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House ∙ 2 guests
Winter Park, Grand County, Colorado, United States
from $131
VRBO
5.0
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Apartment ∙ 4 guests ∙ 1 bedroom
Winter Park, Grand County, Colorado, United States
from $83
VRBO
4.9
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Apartment ∙ 6 guests ∙ 1 bedroom
Winter Park, Grand County, Colorado, United States
from $25
VRBO
4.7
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Vacation Rentals With Fireplaces

Fireplace
Apartment ∙ 5 guests ∙ 1 bedroom
Winter Park, Grand County, Colorado, United States
from $350
VRBO
4.8
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Fireplace
Apartment ∙ 5 guests ∙ 1 bedroom
Winter Park, Grand County, Colorado, United States
from $350
VRBO
4.7
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Fireplace
Apartment ∙ 5 guests ∙ 1 bedroom
Winter Park, Grand County, Colorado, United States
from $350
VRBO
4.6
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Fireplace
Apartment ∙ 5 guests ∙ 1 bedroom
Winter Park, Grand County, Colorado, United States
from $350
VRBO
4.8
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Vacation Homes With Fishing Spots Nearby

Fishing
Apartment ∙ 5 guests ∙ 1 bedroom
Winter Park, Grand County, Colorado, United States
from $350
VRBO
5.0
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Fishing
Apartment ∙ 4 guests ∙ 1 bedroom
Winter Park, Grand County, Colorado, United States
from $71
VRBO
5.0
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Fishing
Apartment ∙ 4 guests
Winter Park, Grand County, Colorado, United States
from $72
VRBO
4.6
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Fishing
Apartment ∙ 8 guests ∙ 2 bedrooms
Winter Park, Grand County, Colorado, United States
from $69
VRBO
4.8
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Apartments With Balconies or Patios

Balcony/Patio
Apartment ∙ 4 guests
Winter Park, Grand County, Colorado, United States
from $300
VRBO
4.5
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Balcony/Patio
Apartment ∙ 4 guests
Winter Park, Grand County, Colorado, United States
from $250
VRBO
4.6
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Balcony/Patio
Apartment ∙ 4 guests
Winter Park, Grand County, Colorado, United States
from $300
VRBO
4.6
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Balcony/Patio
Apartment ∙ 4 guests
Winter Park, Grand County, Colorado, United States
from $78
VRBO
4.7
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Popular Rental Amenities in Winter Park

  • Kitchen (2,080)
  • TV (2,030)
  • Internet (2,020)
  • No smoking (2,015)
  • Fireplace (1,903)
  • Microwave (1,882)
  • Dishwasher (1,796)
  • Washer (1,687)
  • No pets (1,655)
  • Parking (1,534)
  • Fishing (1,131)
  • Balcony/Patio (1,103)
Our search page's filters will help you find the ideal rental in Winter Park. HomeToGo's data reveals that "TVs" and "internet" are the most commonly offered amenities in Winter Park. Plan your vacation in advance if you want a rental with a yard or you travel with your pet. There are just 116 listed rentals with "yards" and 163 properties with "Pets Allowed."

Price and Availability Index Winter Park

Vacation Rental Price Information in Winter Park

The graph shows the average rental prices for the next twelve months in Winter Park. It is during a week of December (12/22 - 12/29) that you will find the highest prices for the next 12 months. Prices decrease in a week of September (9/29 - 10/6), where average prices are $187.

Rental Availability Information in Winter Park

Our availability graph helps you identify the busiest months in Winter Park. The most challenging week to find a rental in the next twelve months is in September (9/7 - 9/14). Conversely, you will find the highest percentage of available offers in Winter Park in November (11/24 - 12/1).

The Weather in Winter Park

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19°
27°
14°
28°
16°
34°
23°
52°
36°
54°
39°
50°
37°
46°
34°
36°
23°
23°
12°
16°
Jan.
Feb.
Mar.
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May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

This is the climate diagram in Winter Park. During July, maximum temperatures go up to more than 53° On the other hand, you could have temperatures dropping under 5° in December. The rainiest month is July while the driest month is March.

Users who are searching for apartment rentals in Winter Park will have a lot of options to choose from, as they are the most typical accomodations being offered in this destination. In addition, the average size of apartment rentals in Winter Park is 1,050 ft² and they cost, on average, $381 a night. Furthermore, if you are going in a group of 6, apartment rentals are the perfect accommodation type in Winter Park, as they usually welcome this exact group size. Users looking for something other than apartment rentals can also compare many house rentals, which are the other most popular accommodation type in Winter Park. The average size of house rentals in Winter Park is 2,390 ft², and the average price is $581 per night.

Ski the slopes and savor superb views with Winter Park vacation homes

Spacious cabin rentals and modern condo vacation rentals in Winter Park put you near all the action on the ski resort's mountainside. Enjoy the woodsy locale and proximity to Colorado's scenic nature.

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Food & Drinks

A variety of mountainside cuisine

Roll into The Ditch On 40 for burgers and Southwestern fare. The menu's signature item, New Mexican Juantons, are egg rolls with a twist, containing green chilis, garlic, ground chuck, and sharp cheddar.

Get your crêpe fix at Goodys Mountain Cafe & Creperie, where their doughy creations along with steaming coffee will keep you racing on the slopes all morning long. For steaks and classic bistro fare in an upscale setting, head to Deno's, which offers everything from pizza and burgers to seafood.

Family Activities

Young mountaineers

Beyond ski school, children can enjoy tubing, ice skating, and snowshoeing. In summer, Winter Park, despite a name reminiscent of endless snow, is just as exciting. The resort's alpine slide is the longest of its kind in mountainous Colorado. Kids can fly down the hill in joy on the safe yet thrilling track.

Treat kids to a day out fishing at one of the area's child-friendly ponds. The stocked North Pond at Lion's Fishing Ponds is suitable for ages 14 and younger, while the stocked pond at Kaibab Park is for those 15 and under. Casting a line should get some bites!

Local Attractions

Adrenaline rushes

Winter Park Ski Resort is one of the top, best-known ski resorts in Colorado, not to mention the longest-running, at 75 years old. Explore seven territories of highly varied terrain, from challenging moguls in Mary Jane Territory to backcountry-like Vasquez Ridge.

Colorado has a collection of 53 extra-tall mountains over 14,000 feet, referred to locally as "14-ers." Winter Park is home to a few of these mammoths, with the closest and least difficult pair being Mount Bierstadt and Mount Evans.

We compare more than 300 providers, including:

Booking.com Vacation Rentals in Winter Park VRBO Vacation Rentals in Winter Park HomeAway Vacation Rentals in Winter Park TripAdvisor Vacation Rentals in Winter Park VacationRentals.com Vacation Rentals in Winter Park HouseTrip Vacation Rentals in Winter Park FlipKey Vacation Rentals in Winter Park Wimdu Vacation Rentals in Winter Park 9flats.com Vacation Rentals in Winter Park VaycayHero Vacation Rentals in Winter Park PerfectPlaces.com Vacation Rentals in Winter Park Homestay.com Vacation Rentals in Winter Park only-apartments Vacation Rentals in Winter Park Interhome Vacation Rentals in Winter Park Bedycasa Vacation Rentals in Winter Park Novasol Vacation Rentals in Winter Park HomeEscape Vacation Rentals in Winter Park

Vacation Destinations Near Winter Park

Top Winter Park Neighborhoods