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. Spiel Haus - Winter Park Luxury Home — Property 312397

    Vacation House rental in Winter Park area
    • House
    • 4 bedrooms , sleeps 16
    • 4 bathrooms
    • lake, mountain
    • washing machine
    Christmas Open!! Book 4 nights, 5th Free
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $2100 - $5250 per property per week

  2. Luxury Townhome in Downtown Winter Park-Private Hot Tub! — Property 210201

    Vacation Townhome rental in Winter Park area
    • Townhome
    • 4 bedrooms , sleeps 12
    • 4 bathrooms
    • 1 half bathroom
    • mountain, town
    • accept credit card
    Rates (shown in USD)
    $1925 - $4200 per property per week

  3. New Winter Park Luxury 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 - $10150 per property per week

  4. Winter Park Vacation Rental - High Mountain Retreat Directly on Shuttle Route — Property 167499

    Vacation House rental in Winter Park area
    • House
    • 5 bedrooms , sleeps 23
    • 4 bathrooms
    • 1 half bathroom
    • mountain, resort
    • washing machine
    Rates (shown in USD)

  5. 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)

  6. Beautiful New Winter Park Town Home, Professionally designed & furnished, VIEWS! — Property 162515

    Vacation Townhome rental in Winter Park area
    • Townhome
    • 4 bedrooms , sleeps 13
    • 4 bathrooms
    • 1 half bathroom
    • mountain
    • accept credit card
    Rates (shown in USD)
    $2345 - $5355 per property per week

  7. Colorado Ski Country Mountain Retreat — Property 100493

    Vacation House rental in Winter Park area
    • House
    • 5 bedrooms , sleeps 15
    • 4 bathrooms
    • mountain, resort
    • washing machine
    Rates (shown in USD)
    $1820 - $3325 per property per week

  8. New, Luxury Townhouse in Downtown Winter Park, Colorado — Property 210199

    Vacation Townhome rental in Winter Park area
    • Townhome
    • 4 bedrooms , sleeps 12
    • 4 bathrooms
    • 1 half bathroom
    • downtown, mountain
    • accept credit card
    Rates (shown in USD)
    $1925 - $4200 per property per week

  9. Luxury 5BR/4.5BA Townhome with Amazing Views! — Property 207909

    Vacation Townhome rental in Winter Park area
    • Townhome
    • 5 bedrooms , sleeps 12
    • 4 bathrooms
    • 1 half bathroom
    • mountain
    • washing machine
    Rates (shown in USD)

  10. Exclusive Ski in Ski Out in a Gated Community at Mary Jane — Property 209234

    Vacation House rental in Winter Park area
    • House
    • 6 bedrooms , sleeps 20
    • 5 bathrooms
    • 1 half bathroom
    • mountain
    • accept credit card
    Rates (shown in USD)

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