Winter Park, CO Cabins & Vacation Rentals

Our Favorite Vacation Rentals in Winter Park

  • Crestview Place Unit 607
     3br Home/Apartment
    RedAwning
    From
    $448
  • New Listing! Ski Haven W/ Hot Tub, Steps To Gondola Condo
     Home/Apartment
    Booking.com
    From
    $284
  • Winter Park Ski-In/Ski-Out Condo w/ Mountain Views
     Home/Apartment
    HolidayLettings
    From
    $450
  • Hideaway Village Columbine 3
     Home/Apartment
    RedAwning
    From
    $282
  • Rendezvous Discovery 3 BR Townhouse
     Country House
    Booking.com
    From
    $342
  • Peaceful mountain condo w/fireplace, porch & grill. Close to bus stop & town!
     2br Home/Apartment
    HolidayLettings
    From
    $326
  • Brand-New 2BR Rendezvous Townhome w/ Patio
     2br Home/Apartment
    RedAwning
    From
    $623
  • Cozens Pointe Condo
     Home/Apartment
    Booking.com
    From
    $291

Check prices for these upcoming dates

Winter Park Vacation Rentals with a Pool

  • Meadow Ridge Court 28 Unit 4
     3br Home/Apartment
    RedAwning
    From
    $463
  • Iron Horse Building C Unit 1023
     Home/Apartment
    RedAwning
    From
    $436
  • Iron Horse Building C Unit 1083
     Home/Apartment
    RedAwning
    From
    $374
  • Iron Horse Building C Unit 4073
     Home/Apartment
    RedAwning
    From
    $375

Winter Park Vacation Rentals with Wi-Fi

  • Twin Rivers By Alderwood Colorado Management
    Nice5br Home/Apartment
    Booking.com
    From
    $185
  • “Hemlock Hideaway” w/ Hot Tub & Stunning Views
     5br Home/Apartment
    RedAwning
    From
    $1,026
  • 2BR w/ Big Views, Patio & Fire Pit
     2br Home/Apartment
    RedAwning
    From
    $592
  • Elegant River Condo w/ Balcony, Close to Skiing
     3br Home/Apartment
    RedAwning
    From
    $1,041

Winter Park Pet-Friendly Vacation Rentals

  • 4BR Fraser Townhome w/Private Deck&Mountain Views
    Nice4br Home/Apartment
    HolidayLettings
    From
    $588
  • Fraser Townhome near Winter Park w/Balcony & Views
     2br Home/Apartment
    HolidayLettings
    From
    $405
  • Creekside Dumont Home w/Deck - Mountain Paradise!
     2br Home/Apartment
    HolidayLettings
    From
    $351
  • NEW! Cozy Ski Condo w/Hot Tubs, 3 Mi to WP Resort!
     3br Home/Apartment
    HolidayLettings
    From
    $422

Winter Park Travel Guide

Winter Park is a quaint small city just north of Orlando. The shaded streets of downtown and its shops and restaurants are a nice break from the chaos of the nearby theme parks and massive resorts.

Things to Do in Winter Park

The Charles Hosmer Morse Museum of American Art and the Mead Botanical Gardens are two of the city's top attractions. In addition, antique and art shows are never hard to find.

Best Time to Visit Winter Park

The best time to visit Winter Park is in early spring when the temperatures are climbing but haven't reach that level of suffocating heat that central Florida is known for. Late fall is also a nice time and you'll find a similar climate.

A Local's Guide to Winter Park Vacation Rentals

It isn’t much of a surprise that the Wintert Park's biggest attractions is its mountain playgrounds and the huge range of winter sports facilities found here. But don’t let this stop you from coming at other times of the year. Winter park is beautiful no matter the season, with its fun-filled summer festivals and the rich colors of the mountains in fall, it is a great year-round destination to book a vacation home.

For those interested in sports, the town has a huge range of lodging possibilities, from slope-side hotels to ski-in-ski-out condos, which make a great base for making use of the facilities in the surrounding area. The Winter Park lodging in town is surrounded by many restaurants that cater for these cold weather activities, with hearty Mexican or German food, perfect for a meal after spending the day on the slopes. There are also plenty of shops where you can pick up some last minute souvenirs or snow gear.

Winter Park Ski Resort is home to some world-class ski slopes, all of which are located in the 3,000 acres of the park. The terrain is diverse enough for everyone to enjoy, from beginner to expert. Several trails have been identified as ‘historical trails’ thanks to the contributions that certain individuals have made to the area, such as the Mary Jane Trail, Bradley’s Bash and Cranmer. However, this is not the only choice of ski resort in the area, nearby you will also find Ski Granby Ranch, Snow Mountain Ranch Nordic Center, and Devil’s Thumb Ranch, which offers plenty of trails for cross-country skiers. Once you have had your fill of skiing, other great snow sports on offer include snowboarding, hayrides, snow tubing and dog sledding to name just a few, all of which combined are sure to make for a great Winter Park vacation. The town of Fraser Valley is also nearby, and is a great place to visit on a day trip from your Winter Park vacation rental.

In summer, the resort is transformed. The slopes are covered in vacationers riding the lifts up to the wildflower-covered mountains and admiring the stunning views. You can also visit the surrounding national forest, and feel at one with nature as you explore the many twisting paths. There are over 600 miles of marked trails for mountain biking, and for those that want a bit of an adrenaline rush, ride the alpine slide or have fun on the summer tubing hill. From Winter Park Colorado it is less than an hour to the Rocky Mountain Nation Park, a postcard-worthy location for exploring the great outdoors and home to the world famous Continental Divide mountain range.

Rentals in Winter Park are extremely popular, especially during ski season, so be sure to book in advance.

Cabins in Winter Park

There is arguably no better place for a skiing adventure than the playground of Winter Park Colorado. With mountain views from many of the Winter Park cabin rentals, you couldn't choose a better family-friendly vacation spot. Winter Park resort is home to world-class skiing, some great eateries, and a range of ski-in ski-out condos.

The Winter Park area and Fraser Valley is also known for its great bike trails over the mountains. Nearby is the Arapaho National Forest, a stunning Grand Country wonderland, with breathtaking views of the Continental Divide. The town of Winter Park has so much to offer, with something for everyone to enjoy.

If you're looking for a Winter Park vacation rental, there's plenty of choice. Most Winter Park lodging comes with a full kitchen, and some even with a hot tub. Trailhead Lodge or Base Village Lofts are just a few examples of the variety of vacation rentals on offer.

Price and Availability in Winter Park

Most expensive
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The cheapest day to stay at a vacation rental in Winter Park tends to be Tuesday, while the most expensive day tends to be Friday. Vacation homes in Winter Park tend to be busiest on Fridays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in Winter Park is in March, while the cheapest month is in September. The most popular time to book a vacation rental in Winter Park is in the high season in March. Winter Park has its low season in May, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Winter Park

Rainy days
41° -14°
1
49° -10°
4
54°
2
60° 13°
3
74° 27°
1
79° 28°
1
77° 31°
1
79° 25°
0
65° -7°
1
55° -10°
1
49° -15°
1
46° -12°
1
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Rainy days

This climate histogram shows you the weather patterns in Winter Park. The hottest month in Winter Park is April, when temperatures peak at 79 ˚F. The coolest month is January, when temperatures drop to -15 ˚F. The wettest month in Winter Park is October with 3.59 inches of rain, while the driest month is April with 0.31 inches of rain.

What Expert Travelers Think

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  • — I use and I recommend AllTheRooms because it is a complete platform. It helps to save a lot of time, it gives all the main information about price, location, and features. In a few steps, I can easily find the best place to stay according to my criteria.

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  • — I love that AllTheRooms has everything in one place when I need to find accommodations that fit my family. Plus it provides all the details I need to help me make the best choice. I often recommend AllTheRooms to friends and family visiting NYC and they agree that it’s a great. Such a time saver!

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Vacation Rentals in Winter Park

Browse rentals from all your favorite providers including Airbnb, RedAwning, Priceline and many more at AllTheRooms.com. We have 4,335 vacation rentals, hotels and other accommodation types in Winter Park ranging from budget options to luxury places to stay. When traveling on a budget, the cheapest place to stay in Winter Park is available at $10 per night. The average price of a vacation rental is around $191 per night.

If you need internet access during your time in Winter Park, then you can choose from over 1,187 accommodations that provide WiFi internet. 50 of our accommodations include a breakfast in the price. Fitness fanatics can get a workout in during their stay by choosing from 461 accommodations that have gym facilities. If you're planning on arriving in Winter Park by car, be sure to choose from 1,108 accommodations that provide parking. We have 540 hotels and vacation rentals that have a pool or jacuzzi.

AllTheRooms has 119 pet-friendly places to stay in Winter Park, so if you're traveling with your pet you won't have any problems.

We combine a wide variety of Winter Park accommodations including vacation rentals, home stays, hostels and other unique places to stay into one easy search. We show results from more than 5 providers, including 1,014 places to stay from Airbnb, 228 accommodations from RedAwning and 101 places to stay from Priceline.

2,013 of our accommodations in Winter Park have been reviewed and rated. 43% are rated excellent or good. 1,872 accommodations allow instant booking.

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