Winter Park Vacation Rentals and Cabins

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Make Winter Park your next getaway—choose from 113 great vacation rentals

Nestled on the cusp of Colorado's Continental Divide in the Arapaho National Forest, our Winter Park vacation rentals and condos offer the most rustic of mountain living, seclusion, and a small town feel rich in mountain history and legend. Just under two hours from Denver International Airport, a little over an hour to Keystone, and an hour and a half to Vail, this year-round mountain escape offers guests of all walks of life and all levels of activity to find a place to play hard, no matter the type of year - it won't surprise any visitor to hear this getaway lovingly called "Colorado's Favorite Playground".

Explore Winter Park condo rentals, townhouses, studios, and more


Condo rentals

View 61 Condo rentals


View 32 Townhouses


View 13 Studios

Winter Park vacation rentals for every getaway

Dog-friendly Hot tub Internet
Timber Lake
3 Bedroom | 4.5 Bath | Sleeps 8

Timber Lake - Winter Park, CO

From $116
Silverado Serenity 3D Tour
2 Bedroom | 2 Bath | Sleeps 6

Silverado Serenity - Winter Park, CO

From $64
Snowblaze Studio 3D Tour
0 Bedroom | 1 Bath | Sleeps 4

Snowblaze Studio - Winter Park, CO

From $49
High Country Retreat 3D Tour
2 Bedroom | 1.5 Bath | Sleeps 7

High Country Retreat - Winter Park, CO

From $68
Bear Trail Villa 3D Tour
4 Bedroom | 3.5 Bath | Sleeps 12

Bear Trail Villa - Winter Park, CO

From $350

View 108 more homes

Recent Winter Park vacation rental reviews

We had such a wonderful time at this home! It was perfect for our family of two adults the three kids, and it would have worked for more people as well. The kitchen is well stocked, the house is comfortable, and the hot tub is glorious. It was really nice to be able to walk to the park and into town for restaurants and coffee. Highly recommend!
Deirdre B. | May 2022
This home was situated on a slight incline allowing great views of the mountains. It was easy to get to and provided enough rooms for our group. Everything we needed was provided to have a comfortable stay.
Jennifer D. | May 2022
the thingd that i loved is how it looks small outside but big inside
Alma D. | May 2022

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
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Easy check-in
Professional cleaning
Professional cleaning

Winter Park Ski Resort

One of the oldest operated ski resorts in Colorado, Winter Park Resort is actually four slopes in one resort, with a grand total of over 3,000 acres of skiing and riding terrain. Our Winter Park ski in ski out rentals offer easy access to the "Seven Territories", with a place for all levels of snow sport enthusiasts.
Never touched snow in your life, or traveling with young ones? Enjoy Winter Park's family-friendly terrain and customer-oriented Ski and Ride School, offering private and group lessons for all ages, a renowned adaptive ski program, and childcare.

Want some truly gorgeous views with a bit more pitch? Take the ride up to Parsenn Bowl - 12,000 feet up, with spectacular views and good intermediate terrain. Feeling frisky? Take a few runs on Vasquez Ridge, where glades hide pockets of powder for the intermediate white gold-seekers; or try Mary Jane, Winter Park's infamous bumpy wonderland.

Advanced skiers and riders won't be able to get enough of Eagle Wind's thick glades and steep trails, and the Cirque's back-country chutes. Need a bit of air? Try out one of the six various terrain parks on Winter Park's main slope.

When it's time to catch your breath, take a pit stop at Lunch Rock Cafe up at the top of Mary Jane, or stop in the Village at Winter Park's base for more dining options. Pamper yourself with Alpenglow Spa in the Village - you may even be able to have a massage therapist come to your Winter Park lodging with their In-Room Service!

If skiing/riding isn't your thing, never fear - there's tubing at the Coca-Cola tubing hill, ski bike lessons, ice skating, and s'mores nights in the Gazebo Plaza, plus plenty of shopping in the Village if you need a souvenir or a new pair of gloves.

Winter Park summer activities

Locals in Winter Park have a saying: "Came for the winter, stayed for the summer". The Continental Divide, which collects up to 29 feet of snow per season, becomes a venerable oasis of outdoor summer activity during the warm months. Known as Mountain Biking USA, Winter Park and Fraser Valley turn from winter wonderland into 600 miles of bike trails for novices and professionals alike. Hiking and chairlift rides offer scenic exploration, and visitors will marvel at the abundance this Rocky Mountain hideaway has to offer, from wildlife to wildflowers.

Horseback riding, hot air balloon rides, mini-golf, and an Alpine Slide keep adventurers busy outside, and when the sun begins to set, Winter Park's nightlife begins. Take your pick from trivia nights, happy hours, family-friendly art classes, and a summer concert series highlighting local artists.

Winter Park day trips

Don't stop in your exploration in town: our Winter Park condos and cabin rentals put you in one of the best spots to enjoy the Colorado Front Range and Summit County - enjoy the bustle of summer in Frisco, on the shores of Dillon Reservoir. Visit quirky, fun-loving Boulder, a little over an hour and a half away. Take a day trip to Estes Park and Rocky Mountain National Forest, or drive through Nederland behind Boulder's Flat Irons to spot old mining and ranching homes, and to see the Continental Divide from every angle.

Whether you're here for a celebration of family and/or friends, a holiday getaway with the kids, or taking some well-deserved time off, a stay in our Winter Park vacation rentals is the open door to your play time - go! Who knows what you might find?

Discover Winter Park

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