Search for vacation rental homes in Winter Park

Winter Park Welcomes You (and Your Entire Group)

Crisp air, bright snow and free reign to leave your worries at home are just a few of the things that a trip to Winter Park will bring to the table. Pack up, bundle up and make your way to the Rocky Mountains and you’ll soon be feeling the delightful rush of vacation success.


Bringing the family to a place like Winter Park Colorado is a pretty safe bet. Mesmerizing scenery made accessible by chair lifts, mountaintop restaurants, snowcats and guided snowshoe tours will include everyone in the fun, so bring along whoever you please.


Kids can take lessons to learn the basics while the more experience skiers head out to reclaim their ski legs, and the more subdued among you can simply ride to the Sunspot Lodge, hang out in the village or find a place by the fire and watch the happy people come and go.


Diverse traveling groups are best accommodated in lodgings that allow for plenty of space, privacy and comfort. Sound like a tall order? Winter Park Vacation Rentals meet the task at hand; each condo, chalet and cabin creates a home-like atmosphere without demanding too much in return. Groups fit well into these lodging situations, so even if you have quite the colorful crew on your hands you shouldn’t worry about going without important amenities or the secure sense that everyone is having a good time.


Breathe easily as you prepare to gather everyone into a manageable herd and show them a good time here in the Winter Park Area. Looking forward to a vacation without hesitation is something to strive for, and this time around, it’s something well within reach.

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  1. 3 Bedroom Downtown Winter Park Townhome w/ HOT TUB — Property 200095

    Vacation Townhome rental in Winter Park area
    • Townhome
    • 3 bedrooms , sleeps 9
    • 3 bathrooms
    • 1 half bathroom
    • mountain
    • accept credit card
    Rates (shown in USD)
    $800 - $3750 per property per week

  2. Gorgeous New Mountain Home, Private Hot Tub, Huge Kitchen, Heated Garage in the — Property 319187

    Vacation House rental in Winter Park area
    • House
    • 3 bedrooms , sleeps 10
    • 2 bathrooms
    • 1 half bathroom
    • mountain, resort
    • washing machine
    Rates (shown in USD)

  3. Pristine Condo on the River with All the Modern Amenities — Property 150407

    Vacation Condo rental in Winter Park area
    • Condo
    • 3 bedrooms , sleeps 8
    • 2 bathrooms
    • river
    • accept credit card
    Rates (shown in USD)

  4. Great Location, Beautiful Home, Glorious Views — Property 146909

    Vacation Cabin rental in Winter Park area
    • Cabin
    • 3 bedrooms , sleeps 10
    • 3 bathrooms
    • 1 half bathroom
    • mountain
    • accept credit card
    Rates (shown in USD)
    $1500 - $2275 per property per week

  5. New Telemark Townhome (Downtown) - 3BR/2BA, Bus Route, Internet — Property 162157

    Vacation Townhome rental in Winter Park area
    • Townhome
    • 3 bedrooms , sleeps 7
    • 2 bathrooms
    • downtown, mountain
    • accept credit card
    Rates (shown in USD)

  6. Luxury, Town Home with Spectacular View — Property 321276

    Vacation Townhome rental in Winter Park area
    • Townhome
    • 3 bedrooms , sleeps 10
    • 3 bathrooms
    • 1 half bathroom
    • mountain, town
    • accept credit card
    Rates (shown in USD)
    $1170 - $3045 per property per week

  7. New 'Lodge at Winter Glen' the Perfect Retreat at 2150 Sq.Ft. — Property 174512

    Vacation Townhome rental in Winter Park area
    • Townhome
    • 3 bedrooms , sleeps 9
    • 3 bathrooms
    • 1 half bathroom
    • mountain
    • accept credit card
    Rates (shown in USD)
    $2093 - $4368 per property per week

  8. On Bus Route, Private Hot Tub, 3/3, Internet, Walk to Town — Property 171637

    Vacation Townhome rental in Winter Park area
    • Townhome
    • 3 bedrooms , sleeps 8
    • 3 bathrooms
    • downtown, mountain
    • accept credit card
    Rates (shown in USD)

  9. Book now for summer, new beds, new hot tub, low rates! — Property 119194

    Vacation Townhome rental in Winter Park area
    • Townhome
    • 3 bedrooms , sleeps 9
    • 2 bathrooms
    • 1 half bathroom
    • lake, mountain
    • accept credit card
    Rates (shown in USD)

  10. Bright, Warm, Inviting Townhome - Private Hot Tub, Child Friendly — Property 144899

    Vacation Townhome rental in Winter Park area
    • Townhome
    • 3 bedrooms , sleeps 9
    • 3 bathrooms
    • downtown, mountain
    • accept credit card
    Rates (shown in USD)
    $875 - $2870 per property per week

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