Rent Luxury Cottages in Cook County

We selected the 85 homes worth renting in this location

Home spotlights in Cook County

Windy City Haven

Windy City Haven

  • 5 guests

  • 2 bedrooms

West Loop, Chicago

Welcome to a distinguished spot nestled in the vibrant pulse of the West Loop! All visitors are skillfully screened for safety and a damage hold is acquired prior to stay.

Loop Luxe

Loop Luxe

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

Welcome to the heart of Chicago's vibrant Loop district, where the ultimate urban oasis awaits. Step into Loop Luxe and experience the perfect blend of style and comfort.

Lost in a Moment

Lost in a Moment

  • 6 guests

  • 3 bedrooms

Chicago Loop, Chicago

This pad right in Chicago's South Loop puts the city at your fingertips. While foodies chow down at the many delicious restaurants on your doorstep, culture vultures can spend the afternoon roaming around the famous Field Museum and other nearby galleries.

Chicagoan Idyll

Chicagoan Idyll

  • 7 guests

  • 3 bedrooms

River West, Chicago

Welcome to a treasured retreat in the warm heart of River West, an unforgettable enclave of Chicago. Against a backdrop of radiant diversity, every visitor becomes an insider.


We selected the top 3% holiday homes in Cook County Cottages

Explore the 85 most perfect homes in our collection

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Most popular homes in Cook County

The Lofted Escape

The Lofted Escape

  • 7 guests

  • 3 bedrooms

Fulton River District, Chicago

Elevated Luxe

Elevated Luxe

  • 5 guests

  • 2 bedrooms

Fulton River District, Chicago

Windy City Retreat

Windy City Retreat

  • 20 guests

  • 10 bedrooms

Chicago Loop, Chicago

Westside Retreat

Westside Retreat

  • 7 guests

  • 3 bedrooms

River West, Chicago

The Jeweller

The Jeweller

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

Chicago Morning

Chicago Morning

  • 8 guests

  • 4 bedrooms

Printer's Row, Chicago

The Chi-town Charm

The Chi-town Charm

  • 3 guests

  • 1 bedrooms

West Loop, Chicago

Hey Mr DJ

Hey Mr DJ

  • 6 guests

  • 2 bedrooms

South Loop, Chicago

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Frequently asked questions

Discover our curated collection of luxury holiday Cottages in Cook County, Illinois, United States. We painstakingly review all homes available in a destination and accept only the top 3% to ensure quality our guests can trust. Each of the Cook County Cottages in our collection comes fully furnished with essential bathroom toiletries, expertly-equipped kitchens and all linens included. Book your dream stay today and should you need some help, our friendly team of experts are on hand to help plan your perfect Cottage break.

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