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Winter Park: Vacation Rental By Owner

Search result 1 to 20 Of 595
  • Property-1 Image 1
    Condo Select Dates for Price
    • 2Bed
    • 2Baths
    • (1) Exceptional
    Winter Park, CO

    Stay and play slopeside at the Iron Horse Resort, a 10-minute walk from the base of Mary Jane Mountain. Beat the crowds and head straight for the lifts or take a... ...more

  • Property-2 Image 1
    Condo Select Dates for Price
    • 2Bed
    • 2Baths
    • (2) Exceptional
    Winter Park, CO

    Worry no more when you stay at this wonderful 2-bedroom, 2-bath condo in Winter Park! Just off of the free shuttle line, this vacation rental provides its guests... ...more

  • Property-3 Image 1
    Condo Select Dates for Price
    • 1Baths
    Winter Park, CO

    Find yourself living the ultimate ski vacation in this oversized studio condo, located steps away from that fresh pow access! After a day on the slopes or... ...more

  • Property-4 Image 1
    Condo Select Dates for Price
    • 1Baths
    • (3) Very Good
    Winter Park, CO

    Studio vacation condo at the Iron Horse, just steps from the Winter Park ski area. A 455 square foot room with a gas fireplace, full kitchen and private balcony.... ...more

  • Property-5 Image 1
    Condo $387 / Nightly
    • 2Bed
    • 2Baths
    • (3) Exceptional
    Winter Park, CO

    Treat yourself to a relaxing Winter Park getaway and stay at this charming 2-bedroom, 2-bathroom vacation rental condo that features sleeping arrangements for 6!... ...more

  • Property-6 Image 1
    Condo Select Dates for Price
    • 2Bed
    • 2Baths
    • (3) Exceptional
    Winter Park, CO

    Take your next vacation to new heights with a trip to Winter Park! This 2-bedroom, 2-bath Silverado I condo is perfectly situated within walking distance to Main... ...more

  • Property-7 Image 1
    Condo $270 / Nightly
    • 1Baths
    • (10) Wonderful
    Winter Park, CO

    Get ready for an epic mountainside getaway when you stay at this vacation rental studio in Winter Park. Accommodating up to 4 guests, the condo offers a full... ...more

  • Property-8 Image 1
    Condo $375 / Nightly
    • 2Bed
    • 2Baths
    • (9)
    Winter Park, CO

    Fall in love with the majesty of the Rocky Mountains in this breathtaking 2-bedroom, 2-bathroom vacation rental condo for 9. Perfect for all seasons, this Winter... ...more

  • Property-9 Image 1
    Condo $302 / Nightly
    • 2Bed
    • 2Baths
    • (16) Wonderful
    Winter Park, CO

    Your idyllic home base for the Rocky Mountains awaits you at this 2-bed, 2-bath vacation rental! Nestled alongside the Fraser River Trail, this top-floor condo... ...more

  • Property-10 Image 1
    Condo $153 / Nightly
    • 1Baths
    • (2) Excellent
    Winter Park, CO

    The mountains await at this cozy 1-bathroom Winter Park vacation rental studio that sleeps 6. With access to resort-level amenities, such as 2 hot tubs, a heated... ...more

  • Property-11 Image 1
    Condo $387 / Nightly
    • 2Bed
    • 2Baths
    • (14) Good
    Winter Park, CO

    Escape to beautiful Winter Park in comfort and style when you stay at this 2-bedroom, 2-bathroom vacation rental condo that sleeps up to 7 lucky travelers. You'll... ...more

  • Property-12 Image 1
    Condo Select Dates for Price
    • 2Bed
    • 2Baths
    • (2) Exceptional
    Winter Park, CO

    Located less than a mile from downtown Winter Park, boasting covered parking, easy access to the Winter Park Resort shuttle, a community hot tub, and comfortable... ...more

  • Property-13 Image 1
    Condo Select Dates for Price
    • 1Baths
    • (3) Very Good
    Winter Park, CO

    Find yourself living the ultimate mountain life in this comfortable ski-in/ski-out studio. You will find this condo has everything you need to unwind after a day... ...more

  • Property-14 Image 1
    Townhome $338 / Nightly
    • 3Bed
    • 4Baths
    • (2)
    Winter Park, CO

    Experience the best of Colorado during your stay at this 3-story townhome in Winter Park. Offering 3 bedrooms, 3.5 bathrooms, and accommodations for 12, this... ...more

  • Property-15 Image 1
    Condo Select Dates for Price
    • 2Bed
    • 2Baths
    Winter Park, CO

    Take your family ski trip to new heights by staying at the Founders Pointe condos in Winter Park! This 2-bedroom, 2-bath vacation rental sits only 150 yards from... ...more

  • Property-16 Image 1
    Townhome Select Dates for Price
    • 5Bed
    • 4Baths
    • (4) Exceptional
    Winter Park, CO

    This exceptional vacation rental townhome is the perfect pick for your Winter Park getaway. Updated, spacious and comfortable, the 5-bedroom, 3.5-bath rental is... ...more

  • Property-17 Image 1
    Condo Select Dates for Price
    • 1Baths
    • (2)
    Winter Park, CO

    Situated in Fraser Crossing and Founders Pointe, this ultimate Winter Park getaway is located just steps from Winter Park Resort and 3 miles from all of... ...more

  • Property-18 Image 1
    Condo Select Dates for Price
    • 1Bed
    • 1Baths
    • (3) Very Good
    Winter Park, CO

    Snow or sunshine, this Winter Park vacation rental is your one-stop-shop for all-season adventures! The condo sits steps from the resort’s new 10-person gondola,... ...more

  • Property-19 Image 1
    Condo $201 / Nightly
    • 1Bed
    • 1Baths
    • (7) Very Good
    Winter Park, CO

    Reconnect with family and friends at this 1-bedroom, 1-bath vacation rental condo, offering a prime location just steps from Winter Park Resort and minutes to all... ...more

  • Property-20 Image 1
    Condo $388 / Nightly
    • 2Bed
    • 3Baths
    • (6) Excellent
    Winter Park, CO

    Book your ideal Winter Park retreat to this 2-bed, 3-bath vacation rental located just over a ½ mile from the resort chairlifts. With enough space to comfortably... ...more

Vacation Rental Filters are an easy way to help you personalize your search to find the ideal rental in Winter Park. Many accommodations in Winter Park provide "Non Smoking Only", there are 137, or there are 129 of Vacation Rentals in Winter Park with a "Children Welcome", there are also 126 with "Skiing", which is another great reason to visit Winter Park.

We analyzed price data and rendered them in this graph, which shows vacation rental prices for the next twelve months in Winter Park. The most expensive month of the next 12 months is in January, where prices hit an average of $112 a night. In , prices will hit an average low of $0 per night.