Winter Park Vacation Rentals and Cabins

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USA > Colorado > Winter Park

Make Winter Park your next getaway—choose from 109 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

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Condo rentals

View 58 Condo rentals
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Townhouses

View 31 Townhouses
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Studios

View 13 Studios

Winter Park vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Iron Horse Studio Retreat 3D Tour
0 Bedroom | 1 Bath | Sleeps 4

Iron Horse Studio Retreat - Winter Park, CO

From $85
Beaver Village 15-11 3D Tour
2 Bedroom | 2 Bath | Sleeps 6

Beaver Village 15-11 - Winter Park, CO

From $105
Hi Country Haus  6-15 3D Tour
1 Bedroom | 1 Bath | Sleeps 4

Hi Country Haus 6-15 - Winter Park, CO

From $66
Mary Jane Chalet
5 Bedroom | 3 Bath | Sleeps 12

Mary Jane Chalet - Winter Park, CO

From $340
Trailhead 611 3D Tour
2 Bedroom | 2 Bath | Sleeps 7

Trailhead 611 - Winter Park, CO

From $123

View 104 more homes

Recent Winter Park vacation rental reviews

Really nice property. Exactly as described. This will be my first choice when I return to Winter Park.
Jon L. | Jan 2022
Great for families or groups. Location is great for walking around town!
Jill C. | Jan 2022
Overall this was a lovely stay. I would recommend anyone looking to spend some time around Winter Park to stay here. That said, there are some things that could be improved. Information about the winter park bus. We tried to take it, but there were issues with there site so couldn't find times it left online. Instructions for the Keurig. These are suppose to be intuitive to operate, but it was either broken or we were doing something wrong. We got about half a cup of coffee out of it for the entire trip :(
Paul M. | Jan 2022

Book confidently. Stay comfortably.

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