Book Luxury Winter Rentals in Cook County

We selected the 23 homes worth renting in this location

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Home spotlights in Cook County

Panorama Place

Panorama Place

  • 6 guests

  • 3 bedrooms

South Loop, Chicago

Chicago is laid out at your feet thanks to the floor-to-ceiling windows of this home. Whether you're watching TV in the white living space, cooking up a feast in the pine kitchen or waking up on the memory foam mattresses in the bedrooms, the skyline is visible.

Gilded Frame

Gilded Frame

  • 3 guests

  • 1 bedrooms

Near North, Chicago

If you’re an art lover looking to visit Chicago, then you’ve come to the right place. River North, where this delightful one-bedroom is located, has the highest concentration of galleries in the US, after Manhattan.

Checking Account

Checking Account

  • 2 guests

  • 1 bedrooms

Near North, Chicago

Get out your Chicago apartment checklist and be prepared to get ticking as this apartment has all you need for your time in the Windy City. You'll find fantastic views through the floor-to-ceiling windows, ideal for admiring while you work at the desk or lounge on the sofa.

Easel And Brush

Easel And Brush

  • 5 guests

  • 2 bedrooms

Near North, Chicago

If you’re visiting Chicago and you're interested in art, then the chic River North neighbourhood is the perfect place to stay. The area is now the city’s art and design quarter, with the highest concentration of galleries in the US after Manhattan.


We selected the top 3% holiday homes in Cook County Vacation Rentals for Winter

Explore the 23 most perfect homes in our collection

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Most popular homes in Cook County

Chicago Morning

Chicago Morning

  • 8 guests

  • 4 bedrooms

Printer's Row, Chicago

Monday Night

Monday Night

  • 3 guests

  • 1 bedrooms

South Loop, Chicago

On Cloud Nine

On Cloud Nine

  • 2 guests

  • 1 bedrooms

Near North, Chicago

Slice Of Sky

Slice Of Sky

  • 3 guests

  • 1 bedrooms

Rush & Division, Chicago

Skyscraper

Skyscraper

  • 3 guests

  • 1 bedrooms

Near North, Chicago

Local Colour

Local Colour

  • 4 guests

  • 2 bedrooms

Near North, Chicago

Solo Bird

Solo Bird

  • 2 guests

  • 1 bedrooms

Near North, Chicago

Swing Swing

Swing Swing

  • 6 guests

  • 3 bedrooms

South Loop, Chicago

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Browse our remarkable collection of luxury Vacation Rentals for Winter in Cook County, Illinois, United States. As only the top 3% of homes go on to become Plum Award winners, you can be certain that your chosen home will be ideal for you. Each home in our range must pass 3 rounds of testing, and comes fully furnished with a well-equipped kitchen, all linen, and essential bathroom toiletries included. Make the most of the chilly season, and wrap up warm in a comfortable Winter Holiday Rental in Cook County. Reach out to our caring team of experts, who love nothing more than helping you discover the perfect home for your trip.

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