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  • Serene & Private Winter Park Ski Chalet w/Hot Tub!

    Winter Park, Colorado

    An epic Winter Park retreat awaits you at this 4-bedroom, 3-bath vacation rental house! This stunning property boasts 2,400 square-feet of well-appointed living space and is sure to suit any group... ...more

    Beds: 4 Baths: 3 Property type: House (0)
    $305 / Nightly
  • Base Village Loft 104

    Winter Park, Colorado

    Enjoy gorgeous leather and wood furnishings, high-end interiors and the most sought after location in the Village at Winter Park Resort when you stay at Base Village Loft 104. Just a two minute... ...more

    Beds: 3 Baths: 3 Property type: House (0)
    $280 / Nightly
  • Cozy Condo w/ Amenities in Heart of Winter Park!

    Winter Park, Colorado

    Discover your own Rocky Mountain paradise with this conveniently located 2-bedroom, 2-bath vacation rental condo in the heart of Winter Park! With accommodations for 6 and access to a plethora of... ...more

    Beds: 2 Baths: 2 Property type: Apartment (1)
    $115 / Nightly
  • NEW! Winter Park Chalet w/ Hot Tub on Bus Route!

    Winter Park, Colorado

    Pack your skis and head off to ‘Swiss Chalet in Winter Park’, a beautiful Swiss Chalet-style mountain home located in the town of Winter Park! With 5 bedrooms, 4 baths, and 6,000 square feet of... ...more

    Beds: 5 Baths: 4 Property type: House (0)
    $482 / Nightly
  • Bright, Updated Top Floor Unit With Great Views

    Winter Park, Colorado

    This bright 952 sq. ft. two bedroom two bath condo has been updated and offers all that you need for your vacation. It is nestled in the back of the complex next to the national forest. This is a... ...more

    Beds: 2 Baths: 2 Property type: Condo (1) Exceptional
    $175 / Nightly
  • Spacious mountain condo w/ private hot tub & jetted tub - close to town!

    Winter Park, Colorado

    This roomy Winter Park penthouse offers beautiful forested views, easy access to town, and a private hot tub. You'll be in a three-story building on the top floor, close to the bus route. This... ...more

    Beds: 3 Baths: 3 Property type: House (0)
    $137 / Nightly
  • Base Camp 496

    Winter Park, Colorado

    Breathtaking 4 bedroom, 4.5 bathroom ski-in/ski-out 3000 square foot luxury town home located on the ski corridor, midway between the Mary Jane and Winter Park lifts. Nestled on the banks of Jane... ...more

    Beds: 4 Baths: 5 Property type: House (0)
    $502 / Nightly
  • Winterwoods Cabin

    Winter Park, Colorado

    This modern rustic cabin was designed with the perfect ski vacation in mind and it has ended up equating to so much more. Strategically located near the base of Winter Park Resort you can access... ...more

    Beds: 4 Baths: 4 Property type: Log Cabin (0)
    $401 / Nightly
  • Zephyr Mountain Lodge 1318

    Winter Park, Colorado

    No more fighting for the biggest bed in this freshly updated condo featuring new King beds and flatscreen TVs in each of the bedrooms, plus a Queen size sofa bed in the lounge. The fully equipped... ...more

    Beds: 2 Baths: 2 Property type: House (0)
    $204 / Nightly
  • Base Camp 490

    Winter Park, Colorado

    Base Camp - Winter Park's most sought after destination is waiting for you! This fabulous ski-in/ski-out 4 bedroom townhome with a private hot tub is already a huge hit with families or larger... ...more

    Beds: 4 Baths: 5 Property type: Apartment (0)
    $502 / Nightly
  • Red Quill 105

    Winter Park, Colorado

    This spacious 3-level 3-bedroom, 3.5 bathroom townhome in Red Quill Village sleeps 8 in beds plus an additional 4 on the sleeper sofa and futon. Beautifully appointed with marble, granite, tile,... ...more

    Beds: 3 Baths: 4 Property type: House (0)
    $220 / Nightly
  • Slopeside 202

    Winter Park, Colorado

    Enjoy the space, comfort, and convenience of this townhome in Old Town. Bay windows, vaulted ceilings and skylights maximize the natural light and open feel of the home. The open layout is perfect... ...more

    Beds: 3 Baths: 3 Property type: House (6) Excellent
    $252 / Nightly
  • Trademark 3-4

    Winter Park, Colorado

    This luxury 3-bedroom, 3 bath, one-level condo is located in Trademark, Winter Park's most prestigious neighborhood. Because it is an end unit, Trademark 3-4 offers spectacular views and... ...more

    Beds: 3 Baths: 3 Property type: Apartment (1) Exceptional
    $251 / Nightly
  • Zephyr Mountain Lodge 2603

    Winter Park, Colorado

    Comfort and convenience are two words to describe this ski in/out condo. Get on the mountain in just minutes, sit back and relax on the balcony, or stroll through the Village at Winter Park Resort... ...more

    Beds: 2 Baths: 2 Property type: House (1) Exceptional
    $208 / Nightly
  • NEW LISTING! Family-friendly condo w/ fireplace & balcony close to ski resort

    Winter Park, Colorado

    This charming condo in Winter Park is the place to be for your next Rocky Mountain adventure! An inviting interior offering a wood-burning fireplace and a balcony overlooking the nearby channel... ...more

    Beds: 2 Baths: 2 Property type: House (0)
    $70 / Nightly
  • Luxury 4BR Cabin w/2 King Masters on Shuttle Route

    Winter Park, Colorado

    Welcome to Alpine Hollow! Experience the Colorado Rocky Mountains like never before from this warm and inviting home, well-situated for the many year-round activities Winter Park has to offer! With... ...more

    Beds: 4 Baths: 3 Property type: House (1) Exceptional
    $290 / Nightly
  • NEW! 3BR Winter Park/Fraser Home w/New Hot Tub!

    Winter Park, Colorado

    Experience local luxury in this spacious 3-bedroom, 3.5-bath vacation rental home that sleeps 10 in the Rendezvous neighborhood of Winter Park, Colorado. There's nearly 2,400 interior square feet... ...more

    Beds: 3 Baths: 4 Property type: House (0)
    $190 / Nightly
  • Winter Park Home w/Ski Hill Views, Sauna & Hot Tub

    Winter Park, Colorado

    Experience the majesty of the Rocky Mountains from the luxury of this 5-bedroom, 4.5-bathroom vacation rental home for up to 12 in Winter Park. After a day on the slopes, there's no better way to... ...more

    Beds: 5 Baths: 5 Property type: House (0)
    $400 / Nightly
  • Elk Trail Retreat

    Winter Park, Colorado

    This quiet two bedroom townhome is situated above the town of winter park on the free bus shuttle route. Close enough to town but far enough away to feel away from it all. With cozy furniture... ...more

    Beds: 2 Baths: 2 Property type: House (0)
    $241 / Nightly
  • Hi Country House 1604

    Winter Park, Colorado

    Located one block off the main street of Winter Park, this one bedroom, one bath has all the comforts you'll need during your stay. There's a pull out queen bed in the sofa and a fully stocked... ...more

    Beds: 1 Baths: 1 Property type: Condo (0)
    $120 / Nightly
Search result 1 to 20 Of 1181

Winter Park: Vacation Rental By Owner

Vacation Rental Filters are an easy way to help you personalize your search to find the ideal rental in Winter Park. Many accommodations in Winter Park provide "Children Welcome", there are 129, or there are 126 of Vacation Rentals in Winter Park with a "Biking", there are also 60 with "Bird Watching", which is another great reason to visit Winter Park.