Winter Park, CO Cabins & Vacation Rentals

Our Favorite Vacation Rentals in Winter Park

  • Iron Horse Studio
    NiceCountry House
  • Family friendly condo w/ mountain views, gas fireplace, & a shared hot tub
     2br Home/Apartment
  • Lakota Trailside Luxury Villa
     Country House
  • Comfy condo near Winter Park w/ shared pool, hot tub & ski shuttle!
     2br Home/Apartment
  • Hi Country Haus Unit 1515
    ExcellentCountry House
  • Trailhead Lodges 524
     3br Home/Apartment
  • Vasquez Penthouse
     Country House
  • Gorgeous Rocky Mountain home w/ a full kitchen, shared tennis, & amazing views
     4br Home/Apartment

Check prices for these upcoming dates

Winter Park Vacation Rentals with a Pool

  • $74 Fall Colors, King Bed, New Rec Center
    Excellent2br Home/Apartment
  • 2BR with hot tub & mountain views
    Excellent2br Home/Apartment

Winter Park Vacation Rentals with Wi-Fi

  • Village of Winter Park Condo
  • Fantastic Winter Park Condo for Families & Groups!
    Excellent3br Home/Apartment
  • Spacious pet-friendly chalet on free shuttle route with beautiful views
    Good5br Home/Apartment
  • Meadow Chalet, new luxury home in Winter Park
    Excellent3br Home/Apartment

Winter Park Pet-Friendly Vacation Rentals

  • Comfortable condo near downtown w/ deck, grill & shared hot tub!
     2br Home/Apartment
  • Trappers Home 450 (***********)
     4br Home/Apartment
  • Tabernash Townhome w/ Private Hot Tub & Mtn Views!
     4br Townhouse
  • Riverside Winter Park Condo w/ Hot Tub Access!
    Excellent2br Home/Apartment

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
45° -6°
43° -10°
51° -11°
39° -19°
71° 23°
79° 29°
79° 31°
79° 31°
74° 25°
Rainy days

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

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Vacation Rentals in Winter Park

At we have rentals from all of the leading providers - Airbnb, RedAwning, Agoda and many more. We have 4,938 vacation rentals, hotels and other places to stay in Winter Park ranging from inexpensive options to extravagant places to stay. A trip to Winter Park can be affordable - the lowest price accommodation is available at $10 per night. An average vacation rental in Winter Park costs on average $189 a night.

If you need an internet connection during your stay in Winter Park, then you can choose from over 1,657 places to stay that have WiFi internet. 61 of our accommodations come with breakfast in the price. Fitness addicts can get a workout in during their stay by choosing from 633 accommodations that have gyms. If you're planning on getting to Winter Park by car, be sure to choose from 1,604 accommodations that provide parking. 630 places to stay come with a pool or jacuzzi

If you're traveling with your best friend, then make sure to choose one of the 124 pet-friendly accommodations available.

AllTheRooms compares vacation rentals, hotels and other unique accommodation types from many providers in Winter Park, including 927 places to stay from Airbnb, 257 accommodations from RedAwning and 6 places to stay from Agoda

1,843 of the accommodations in Winter Park have been reviewed by previous guests. They rated 40% as great. 1,960 accommodations allow instant booking.

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