Rent Luxury Accommodation for Groups in Cook County

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

Windy City Wonder

Windy City Wonder

  • 12 guests

  • 6 bedrooms

West Loop, Chicago

Planning a large group getaway to Chicago, but don’t want to get under each other’s toes? This trio of apartments in the same high-end serviced apartment complex should do the trick.

Skyline Reverie

Skyline Reverie

  • 7 guests

  • 3 bedrooms

River West, Chicago

High above River West, this spectacular home with skyline views invites you to experience Chicago at its most inspiring. Floor-to-ceiling windows keep the city close at every moment, while the balcony gives you a private stage for sunrise coffees and evening cocktails under glittering lights.

The High Way

The High Way

  • 4 guests

  • 2 bedrooms

Rush & Division, Chicago

This smart city sanctuary boasts incredible views across the Chicago skyline. The rooms have been thoughtfully designed to inspire ease and relaxation.

Urban Vistas

Urban Vistas

  • 4 guests

  • 2 bedrooms

Rush & Division, Chicago

This Illinois apartment won us over the moment we clapped eyes on the sweeping views of Chicago’s skyline and that private balcony. But the perks don’t end there.


We selected the top 3% holiday homes in Cook County Accommodation for Groups

Explore the 36 most perfect homes in our collection

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Most popular homes in Cook County

Westside Retreat

Westside Retreat

  • 7 guests

  • 3 bedrooms

River West, Chicago

WindyCity Wonders

WindyCity Wonders

  • 5 guests

  • 2 bedrooms

West Loop Gate, Chicago

Metropolis Respite

Metropolis Respite

  • 7 guests

  • 3 bedrooms

Fulton River District, Chicago

Chicago Vista

Chicago Vista

  • 6 guests

  • 2 bedrooms

Rush & Division, Chicago

The West-Loop Wavelength

The West-Loop Wavelength

  • 17 guests

  • 8 bedrooms

West Loop, Chicago

Windy City Haven

Windy City Haven

  • 5 guests

  • 2 bedrooms

West Loop, Chicago

Charming Chicago Charm

Charming Chicago Charm

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

Elevated Luxe

Elevated Luxe

  • 5 guests

  • 2 bedrooms

Fulton River District, Chicago

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Check upcoming rates & availability for Cook County Accommodation for Groups


Frequently asked questions

Reserve a stay in one of the impeccable homes in our collection of luxury Group Holiday Accommodation in Cook County, Illinois, United States. You won't find such consistent quality anywhere else, as every single Plum Guide home comes fully furnished with all linens, a brilliantly-equipped kitchen, and essential bathroom toiletries included. Our experts really do obsess over the smallest details, with shower pressure and a bedroom's decibel levels being tested to ensure absolute quality in your hunt for the perfect home. Rent Cook County Accommodation for Groups today, and learn the true meaning of luxury. Call on our team of experts too, who can help you through the booking process and guarantee that you end up with the ultimate home for you.

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