Cook County Guest Houses

We selected the 36 homes worth renting in this location

Who's coming along?

Adults

Age 13+

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Children

Age 1 to 12

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Infants

Under 1

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Pets

An extra fee may apply

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Home spotlights in Cook County

The Chi-town Charm

The Chi-town Charm

  • 3 guests

  • 2 bedrooms

West Loop, Chicago

Set in the heart of Chicago’s buzzing West Loop, this modern apartment is the perfect base for exploring the city. Step outside and you’re moments from acclaimed restaurants, vibrant markets and cultural landmarks – but when you’re not out and about, the building has plenty to keep you entertained.

The Lion

The Lion

  • 5 guests

  • 2 bedrooms

Rush & Division, Chicago

This home is the perfect place to relax and enjoy your stay in Chicago. The home is located in the Gold Coast neighborhood, which is known for its luxury shops, fine dining, and lake Michigan charm.

Culture Haven

Culture Haven

  • 12 guests

  • 4 bedrooms

Rush & Division, Chicago

Welcome to The Hermes! Nestled in the vibrant Streeterville neighborhood, classic charm meets culture and bustling downtown lifestyle in the heart of The Windy City.

Chicago Chic

Chicago Chic

  • 4 guests

  • 2 bedrooms

Chicago Loop, Chicago

This pet-friendly apartment in Downtown Chicago puts the best of the city at your feet. Millennium Park, The Art Institute, theatres, restaurants, and shops are all just a short stroll away.


We selected the top 3% holiday homes in Cook County Guest Houses

Explore the 36 most perfect homes in our collection

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Most popular homes in Cook County

Loop Haven

Loop Haven

  • 12 guests

  • 6 bedrooms

Chicago Loop, Chicago

The West Wind Charm

The West Wind Charm

  • 5 guests

  • 2 bedrooms

West Loop, Chicago

Chicago Morning

Chicago Morning

  • 8 guests

  • 4 bedrooms

Printer's Row, Chicago

The Windy City Retreat

The Windy City Retreat

  • 5 guests

  • 2 bedrooms

West Loop, Chicago

All Things Glow

All Things Glow

  • 3 guests

  • 2 bedrooms

Hyde Park, Chicago

The Heart of the Loop

The Heart of the Loop

  • 16 guests

  • 8 bedrooms

Chicago Loop, Chicago

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Check upcoming rates & availability for Cook County Guest Houses


Frequently asked questions

Looking for guesthouse style accommodation in Cook County, Illinois, United States? You've come to the right place: Our homes come fully furnished with well-equipped kitchens, toiletries in bathrooms & all linen included. Book today and enjoy a short or extended stay in the best guesthouse style accommodation that Cook County, Illinois, United States has to offer. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

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