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+

0

Children

Age 1 to 12

0

Infants

Under 1

0

Pets

An extra fee may apply

0

Home spotlights in Cook County

Chicago Vista

Chicago Vista

  • 6 guests

  • 2 bedrooms

Rush & Division, Chicago

Step inside The Leto, where classic charm mingles with vibrant culture in the bustling Streeterville neighborhood of Chicago. This locale promises an immersive experience into not only traditional Chicago history but also the nuances of Italian villa architecture and other globally inspired design details.

Artists' Rendezvous

Artists' Rendezvous

  • 5 guests

  • 2 bedrooms

West Loop, Chicago

Make a date with The Blues, a delightful haven nestled in the West Loop. This home away from home exudes an unmistakable charm, harmonising old-world coziness with a dash of modernity.

The West Wind Charm

The West Wind Charm

  • 5 guests

  • 2 bedrooms

West Loop, Chicago

Welcome to a dazzling retreat in the heart of West Loop. A vibrant ambience invites you to immerse yourself, enveloped by the rhythm of the city's live music and savory aromas from nearby culinary gems.

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.


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

Explore the 36 most perfect homes in our collection

View on map

Most popular homes in Cook County

Urban Vistas

Urban Vistas

  • 4 guests

  • 2 bedrooms

Rush & Division, Chicago

Westside Retreat

Westside Retreat

  • 7 guests

  • 3 bedrooms

River West, Chicago

Windy City Wonder

Windy City Wonder

  • 12 guests

  • 6 bedrooms

West Loop, Chicago

Skyline Reverie

Skyline Reverie

  • 7 guests

  • 3 bedrooms

River West, Chicago

Charming River Retreat

Charming River Retreat

  • 14 guests

  • 6 bedrooms

River West, Chicago

Chicago Heights

Chicago Heights

  • 4 guests

  • 2 bedrooms

Chicago Loop, Chicago

The West-Loop Wavelength

The West-Loop Wavelength

  • 17 guests

  • 8 bedrooms

West Loop, Chicago

The Chicago River Rhapsody

The Chicago River Rhapsody

  • 14 guests

  • 6 bedrooms

River West, Chicago

View all

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.

Search Our Collection