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. New Luxury Ski-in/Ski-Out Condo in Resort Village, Amazing Views — Property 200486

    Vacation Condo rental in Winter Park area
    • Condo
    • 2 bedrooms , sleeps 8
    • 2 bathrooms
    • mountain, resort
    • accept credit card
    25% Off For Weekly Rentals
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1313 - $2240 per property per week

  2. Bear Crossing, 3 Bedroom, 3.5 Bath, Stunning Townhome! — Property 207666

    Vacation Condo rental in Winter Park area
    • Condo
    • 3 bedrooms , sleeps 6
    • 3 bathrooms
    • 1 half bathroom
    • mountain, town
    • washing machine
    Rates (shown in USD)
    $1750 - $4025 per property per week

  3. Beautiful well-kept townhome w/ private hot tub; Great location — Property 153131

    Vacation Townhome rental in Winter Park area
    • Townhome
    • 3 bedrooms , sleeps 8
    • 3 bathrooms
    • mountain, village
    • washing machine
    Rates (shown in USD)

  4. Slopeside Townhome — Property 102339

    Vacation Townhome rental in Winter Park area
    • Townhome
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • 1 half bathroom
    • mountain, resort
    • washing machine
    Rates (shown in USD)

  5. 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)

  6. 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)

  7. ski in ski out, one bedroom ground level, next to hot tub! — Property 208894

    Vacation Condo rental in Winter Park area
    • Condo
    • 1 bedroom , sleeps 6
    • 1 bathroom
    • mountain, resort
    • swimming pool
    Rates (shown in USD)
    $200 - $1953 per property per week

  8. Spacious town home with private hot tub and Internet — Property 153891

    Vacation Townhome rental in Winter Park area
    • Townhome
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • 1 half bathroom
    • mountain, resort
    • washing machine
    Rates (shown in USD)
    $875 - $2450 per property per week

  9. Duplex on Bus Route, Private Hot Tub, in Town........... — Property 319186

    Vacation House rental in Winter Park area
    • House
    • 3 bedrooms , sleeps 8
    • 2 bathrooms
    • mountain, town
    • washing machine
    Rates (shown in USD)

  10. 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)

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