Winter Park, CO Cabins & Vacation Rentals

Our Favorite Vacation Rentals in Winter Park

  • Slopeside 204 Kinney Townhouse
     Country House
  • Lakota Luxury Villa Next to Resort with Amazing Views - Free Activities Daily
     Country House
  • Beaver Condo 16-31
  • Vasquez Run B201 Condo
  • Hi Country Haus - 13-15 Condo
  • 356 Mountain Willow Townhome at Grand Park
     Country House
  • Antler Chalet Home
     Country House
  • Mountain Terrace Townhouse
     Country House

Check prices for these upcoming dates

Winter Park Vacation Rentals with a Pool

  • On the Slopes in 5 minutes! Spacious and Cozy 2BR
    Excellent2br Home/Apartment
  • Mountain porch view, hot tub, fireplace, ski bus
  • 2BR with hot tub & mountain views
    Excellent2br Home/Apartment

Winter Park Vacation Rentals with Wi-Fi

  • Oversized 1bed Ski In/Out MTN VIEWS King&Qn beds
    ExcellentCountry House
  • New Listing! Luxury Mountain Home, Near Skiing
    Excellent3br Home/Apartment
  • The Painted Studio
  • 345 Timberlake Way: 3Br + Bunk Rm +Loft!!
    Excellent4br Home/Apartment

Winter Park Pet-Friendly Vacation Rentals

  • Great for Families & Couples
  • St. Mary's Glacier Condo with Lake Views!
  • Starlight Cabin - Creek & National Forest trails
    Good2br Home/Apartment
  • MAD MIKE'S MOUNTAIN CHALET....your gateway to fun!

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
Most availability
, , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0
Powered by:
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
43° -10°
51° -11°
39° -19°
71° 23°
79° 29°
79° 31°
79° 31°
74° 25°
45° -6°
Rainy days

This climate histogram shows you the weather patterns in Winter Park. The hottest month in Winter Park is July, when temperatures peak at 79 ˚F. The coolest month is November, when temperatures drop to -19 ˚F. The wettest month in Winter Park is September with 2.09 inches of rain, while the driest month is August with 0.37 inches of rain.

What Expert Travelers Think

  • — When I plan a trip, I no longer waste time visiting multiple websites in search of the best accommodations. Now, I just go to AllTheRooms and immediately find everything from luxury villas to pet-friendly rentals! All in one place

    Whitney Wear
    Whitney WearTravel Better Guide
  • — My favorite thing about AllTheRooms is that it combines both rentals and hotels available so you can see an entire view of what is available in a certain area. I was able to see listings on AllTheRooms that I never even saw on other travel sites!

    Daniella Flores
    Daniella FloresILIKETODABBLE
  • — I love AllTheRooms because it enables me to compare a range of providers in just one search. I'd normally spend time checking prices across a range of platforms by visiting different websites one-by-one, so this helps me to save time on my accommodation searches while planning my upcoming trips

    Kacie Morgan
    Kacie MorganThe Rare Welsh Bit

Vacation Rentals in Winter Park

At we have rentals from all of your favorite providers - Airbnb, RedAwning, Agoda and others. Winter Park has 5,323 hotels, vacation rentals and other unique places to stay, with prices to suit careful travellers, luxury travelers and everything in between. For those trying to keep costs down, the lowest priced place to stay in Winter Park is only $10 per night. On average, an accommodation in Winter Park will cost you $196 per night.

Those looking to get some work done during their trip to Winter Park can pick from 1,195 places to stay that include WiFi. 66 places to stay include a morning meal. You can maintain your workout routine by staying at one of 447 accommodations that provide gym facilities. Driving to Winter Park? Then choose one of the 1,166 places to stay that comes with a parking spot included. We have 570 vacation rentals that have a pool or jacuzzi.

If you're traveling with your best friend, then make sure to select one of the 122 pet-friendly accommodations available.

In Winter Park AllTheRooms currently aggregates hotels, vacation rentals, hostels from more than 6 providers, including 1,011 places to stay from Airbnb, 6 accommodations from RedAwning and 6 places to stay from Agoda.

1,834 accommodations in Winter Park have been reviewed; 38% are rated highly. 2,117 accommodations allow instant booking.

Destinations near Winter Park

  • Breckenridge23,514 Properties
  • Steamboat Springs18,665 Properties
  • Keystone12,339 Properties
  • Vail10,359 Properties
  • Aspen5,177 Properties
  • Telluride5,145 Properties
  • Estes Park4,822 Properties
  • Denver4,543 Properties
  • Frisco4,167 Properties
  • Avon4,064 Properties
  • Silverthorne3,854 Properties
  • Snowmass3,803 Properties
  • Beaver Creek3,677 Properties
  • Pagosa Springs3,588 Properties
  • Colorado Springs3,432 Properties
  • Copper Mountain3,394 Properties
  • Fraser2,374 Properties
  • Dillon1,944 Properties
  • Durango1,747 Properties
  • Fort Collins1,370 Properties
  • Crested Butte1,303 Properties
  • Granby1,258 Properties
  • Grand Lake1,092 Properties
  • Boulder1,070 Properties
  • Blue River1,009 Properties
  • Lakewood989 Properties
  • Edwards948 Properties
  • Grand Junction945 Properties
  • Salida934 Properties
  • Englewood767 Properties
  • Ouray740 Properties
  • Glenwood Springs708 Properties
  • Buena Vista673 Properties
  • Pueblo604 Properties
  • Leadville582 Properties
  • Loveland578 Properties
  • Golden563 Properties
  • Westminster559 Properties
  • Arvada515 Properties
  • Longmont512 Properties
  • South Fork505 Properties
  • Evergreen487 Properties
  • Rico435 Properties
  • Aurora428 Properties
  • Ridgway425 Properties
  • Woodland Park424 Properties
  • Thornton418 Properties
  • Greeley407 Properties
  • Manitou Springs403 Properties
  • Gunnison395 Properties
  • Monument382 Properties
  • Littleton379 Properties
  • Carbondale375 Properties
  • Lake City365 Properties
  • Broomfield347 Properties
  • Cortez345 Properties
  • Montrose302 Properties
  • Castle Rock279 Properties
  • Eagle276 Properties
  • Mancos274 Properties
  • Canon City246 Properties
  • Greenwood Village239 Properties
  • Highlands Ranch223 Properties
  • Tabernash221 Properties
  • Centennial213 Properties
  • Silverton210 Properties
  • Louisville202 Properties
  • Dolores187 Properties
  • Cripple Creek167 Properties
  • Morrison151 Properties
  • Idaho Springs136 Properties
  • Allenspark88 Properties
  • Red Feather Lakes84 Properties
  • Twin Lakes72 Properties
  • Monarch51 Properties