Winter Park Vacation Rentals and Cabins

Compare 119 vacation rentals with savings up to 30% off this summer.
USA > Colorado > Winter Park

Make Winter Park your next getaway

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 65 Condo rentals


View 27 Townhouses


View 15 Studios

Winter Park vacation rentals for every getaway

Dog-friendly Hot tub Internet
Winter Escape
2 Bedroom | 2 Bath | Sleeps 6

Winter Escape - Winter Park, CO

$154 avg / night
Snowblaze Studio
0 Bedroom | 1 Bath | Sleeps 4

Snowblaze Studio - Winter Park, CO

$93 avg / night
Hi Country Haus 14-5
1 Bedroom | 1 Bath | Sleeps 2

Hi Country Haus 14-5 - Winter Park, CO

$101 avg / night
Hi Country Haus Getaway
1 Bedroom | 1 Bath | Sleeps 4

Hi Country Haus Getaway - Winter Park, CO

$99 avg / night
Modern Mountain Chalet
2 Bedroom | 2 Bath | Sleeps 6

Modern Mountain Chalet - Winter Park, CO

$201 avg / night

View 114 more homes

Recent Winter Park vacation rental reviews

This place is cozy, functional and walking distance from good coffee/food/hiking/drinks. The hot tub is also an amazing way to end the day. Can’t wait to go back.
Madeline G. | May 2023
We have visited Winter Park twice a year for the past 8 years and this is our favorite place we have stayed. The location is number one!!! Walkable to the great places in town. Great park for the family to enjoy and the hot tube and pool were the absolute best. Spent several days enjoying the close trails, skiing, mountain biking, etc. the space was perfect size and perfectly set up for our family if 5! Beds great! The family absolutely loved it. As a geek my favorite two things were the cool outdoor library and great coffee set up - pour over and grinder absolutely made me feel like I was at home not to mention the best coffee shop in Colorado “Unravel” is right by the complex…it was perfect! Lastly it being ground floor was a plus and could park right next to the unit so the gear and baggage was super easy to get in and out.
Russ P. | May 2023
I booked this condo last minute for some healing after a long term relationship ended and I needed space, and I am so glad I did. It’s a cozy place, I worked remotely the whole time and never had issues with wi-fi, and I am glad I was able to bring my dog with me!
Madeline S. | Apr 2023
Winter Park vacation rental FAQ

Yes, 52 of our Winter Park homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 289 of our Winter Park vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >

Some of the most popular amenities in our Winter Park vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Winter Park team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Winter Park, log in to Trip Manager to see options available for your specific trip.

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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