Winter Park, CO Cabins & Vacation Rentals

Check prices for these upcoming dates

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
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
41° -14°
1
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Feb
Rainy days

This climate histogram shows you the weather patterns in Winter Park. The warmest months in Winter Park are April and June, when temperatures reach 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

  • — I love All the Rooms because instead of having to check one place for home rentals, another for hotel, another for bed and breakfasts, and yet another for a room rental in a private residence, I can finally see EVERYTHING at one site; saving me considerable time

    Jeff Campbell
    Jeff CampbellMiddle Class Dad
  • — I love how AllTheRooms shows a map with room price tags straight away when you search, it makes it so quick and easy to choose the right hotel, at the right price in the right location. Perfect for those with busy lifestyles! The AllTheRooms website is so user friendly. WiFi. Brilliant!

    Amanda Alston
    Amanda AlstonAmanda Alston
  • — 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.

    My Anasa
    My AnasaMy Anasa

Vacation Rentals in Winter Park

At AllTheRooms.com we have accommodations from all of the leading providers - Airbnb, RedAwning, Priceline and more. Winter Park has 4,438 hotels, vacation rentals and other special places to stay, with prices to suit careful travellers, extravagant travelers and everything in between. A trip to Winter Park can be affordable - our cheapest price accommodation is available at $10 per night. A typical vacation rental in Winter Park costs on average $189 a night.

If you would like to stay connected during your trip, then you can choose from over 1,383 accommodations in Winter Park that have WiFi. 51 of our accommodations come with breakfast in the price. You can keep up with your workout routine by staying at one of 502 accommodations that provide gym facilities. If you are driving to Winter Park, you'll want to pick from 1,173 places to stay that provide parking. 562 places to stay come with a pool or jacuzzi

AllTheRooms has 129 pet-friendly places to stay in Winter Park, so if you're traveling with your pet you won't have any trouble.

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 1,030 places to stay from Airbnb, 271 accommodations from RedAwning and 101 places to stay from Priceline.

2,093 accommodations in Winter Park have been reviewed; 45% are rated highly. 1,897 accommodations allow instant booking.

Destinations near Winter Park

  • Breckenridge20,770 Properties
  • Steamboat Springs14,030 Properties
  • Keystone10,658 Properties
  • Vail9,180 Properties
  • Estes Park4,945 Properties
  • Aspen4,706 Properties
  • Telluride4,154 Properties
  • Denver4,047 Properties
  • Avon3,884 Properties
  • Beaver Creek3,637 Properties
  • Frisco3,567 Properties
  • Silverthorne3,482 Properties
  • Colorado Springs3,378 Properties
  • Snowmass3,191 Properties
  • Pagosa Springs3,041 Properties
  • Copper Mountain2,781 Properties
  • Fraser2,032 Properties
  • Dillon1,781 Properties
  • Durango1,453 Properties
  • Fort Collins1,261 Properties
  • Granby1,244 Properties
  • Crested Butte1,236 Properties
  • Grand Lake1,163 Properties
  • Boulder986 Properties
  • Blue River934 Properties
  • Lakewood917 Properties
  • Grand Junction895 Properties
  • Edwards862 Properties
  • Salida760 Properties
  • Ouray715 Properties
  • Englewood702 Properties
  • Glenwood Springs660 Properties
  • Buena Vista654 Properties
  • Leadville564 Properties
  • Loveland563 Properties
  • Golden533 Properties
  • Pueblo521 Properties
  • Arvada515 Properties
  • Westminster498 Properties
  • Longmont465 Properties
  • Woodland Park462 Properties
  • Evergreen441 Properties
  • South Fork439 Properties
  • Ridgway403 Properties
  • Thornton401 Properties
  • Littleton379 Properties
  • Greeley373 Properties
  • Manitou Springs371 Properties
  • Monument358 Properties
  • Aurora349 Properties
  • Carbondale348 Properties
  • Rico346 Properties
  • Gunnison331 Properties
  • Broomfield302 Properties
  • Cortez299 Properties
  • Lake City275 Properties
  • Montrose270 Properties
  • Castle Rock251 Properties
  • Eagle249 Properties
  • Mancos240 Properties
  • Canon City209 Properties
  • Centennial205 Properties
  • Greenwood Village192 Properties
  • Highlands Ranch192 Properties
  • Louisville188 Properties
  • Tabernash186 Properties
  • Silverton180 Properties
  • Cripple Creek177 Properties
  • Dolores166 Properties
  • Morrison140 Properties
  • Idaho Springs127 Properties
  • Red Feather Lakes88 Properties
  • Allenspark82 Properties
  • Twin Lakes49 Properties
  • Monarch40 Properties