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. Home in Elk Run, 4 Bedroom, Hot Tub, Garage, Close to Town — Property 142989

    Vacation House rental in Winter Park area
    • House
    • 4 bedrooms , sleeps 12
    • 3 bathrooms
    • 1 half bathroom
    • mountain, town
    • accept credit card
    Rates (shown in USD)

  2. New 4 Bedroom, Private Hot Tub, in Town, Internet, Bus Route — Property 172525

    Vacation Townhome rental in Winter Park area
    • Townhome
    • 4 bedrooms , sleeps 10
    • 3 bathrooms
    • downtown, mountain
    • accept credit card
    Rates (shown in USD)

  3. Beautiful Townhome w/ Private Hot Tub in the Heart of WP — Property 175894

    Vacation Townhome rental in Winter Park area
    • Townhome
    • 4 bedrooms , sleeps 8
    • 3 bathrooms
    • downtown, mountain
    • washing machine
    Rates (shown in USD)
    $1750 - $2100 per property per week

  4. Brand New Lakota Townhome, Great Views, Private Hot Tub — Property 321105

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

  5. Private Home Luxury in the Pines — Property 212683

    Vacation House rental in Winter Park area
    • House
    • 4 bedrooms , sleeps 12
    • 3 bathrooms
    • mountain, town
    • swimming pool
    Rates (shown in USD)
    $1350 - $3150 per property per week

  6. Beautiful Mountain Home - Luxury in Rustic Mountain setting — Property 152394

    Vacation House rental in Winter Park area
    • House
    • 4 bedrooms , sleeps 14
    • 3 bathrooms
    • mountain
    • accept credit card
    Rates (shown in USD)
    $1710 - $4550 per property per week

  7. Immaculate Family Home on the Award Winning Pole Creek Golf Course — Property 319422

    Vacation House rental in Winter Park area
    • House
    • 5 bedrooms , sleeps 14
    • 4 bathrooms
    • 1 half bathroom
    • mountain, town
    • washing machine
    Rates (shown in USD)

  8. Location-Ski Lifts in View-Heated Garage-1st Stop on Shuttle — Property 128840

    Vacation Condo rental in Winter Park area
    • Condo
    • 4 bedrooms , sleeps 11
    • 3 bathrooms
    • mountain, resort
    • washing machine
    Rates (shown in USD)
    $2275 - $2975 per property per week

  9. Brand New Winter Park Estate: Fireside at Dreamcatcher — Property 180298

    Vacation House rental in Winter Park area
    • House
    • 5 bedrooms , sleeps 17
    • 5 bathrooms
    • 1 half bathroom
    • mountain
    • accept credit card
    Rates (shown in USD)
    $5250 - $9800 per property per week

  10. 4 Bd/3.5 BA Luxury Townhome-Walk to Base-Spectacular Mtn. View — Property 192927

    Vacation Townhome rental in Winter Park area
    • Townhome
    • 4 bedrooms , sleeps 12
    • 3 bathrooms
    • 1 half bathroom
    • mountain, town
    • accept credit card
    Rates (shown in USD)
    $1575 - $5250 per property per week

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