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. Winter Park Condo- Discount Rates-FREE High Speed Wireless Internet — Property 158648

    Vacation Condo rental in Winter Park area
    • Condo
    • 2 bedrooms , sleeps 8
    • 2 bathrooms
    • downtown, mountain
    • swimming pool
    Rates (shown in USD)
    $595 - $725 per property per week

  2. Fabulous Spring/Summer Pricing from $56/night...Let's Make a Deal!! — Property 148441

    Vacation Condo rental in Winter Park area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • mountain, village
    • accept credit card
    Rates (shown in USD)
    $395 - $1960 per property per week

  3. 'Base Camp' in Winter Park, 2BR Condo Accesses All Activities Year-Round — Property 139893

    Vacation Condo rental in Winter Park area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • mountain, town
    • accept credit card
    Rates (shown in USD)
    $450 - $1650 per property per week

  4. 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 - $2730 per property per week

  5. Backs to National Forest and Two Minutes From Downtown — Property 150479

    Vacation Condo rental in Winter Park area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 half bathroom
    • washing machine
    • internet access
    Rates (shown in USD)
    $570 - $1110 per property per week

  6. 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)
    $1750 - $3220 per property per week

  7. State-of-the-Art, 5 Bedroom Home — Property 188626

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

  8. 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)

  9. 2 Bed, 2 Bath River Condo — Property 319184

    Vacation Condo rental in Winter Park area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • mountain, town
    • swimming pool
    Rates (shown in USD)

  10. 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
    • mountain, river
    • accept credit card
    Rates (shown in USD)

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