Colorado Vacation Rentals In Winter Park

Winter Park is an amazing getaway no matter the season, packed with outdoor events, activities and festive celebrations. StayWinterPark has put together a fantastic resource to assist you in planning your summer adventure, ensuring you don't miss out on anything!

You can pick from our downtown rentals that are just a stroll away from most events, charming cabins for a peaceful retreat or spacious private homes perfect for family reunions or larger groups.

Search by month & pick which holiday you'd like to celebrate in Winter Park this year: May, June, July, August, September, October, November, December

SEARCH BY HOLIDAY OR BY MONTH

Search our available rentals for all the special occasions and events happening in 2025! We have Winter Park Rentals available for each month and offer Flexible check-in accommodations if you are visiting Winter Park for a quick weekend trip, mid-week getaway or renting for the entire week! We have something perfect for your next special occasion and would love to host you in one of our 5-star vacation rentals in Winter Park.

Select a month below & pick which holiday you'd like to celebrate in Winter Park this year:

May, June, July, August, September, October, November, December

May 2025 Holiday's & Events

Mother's Day

Colorado Vacation Rentals In Winter Park

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