Book Luxury Holiday Rentals in Cook County

Award-winning homes from £98

Home spotlights in Cook County

The Jeweler's Gem

The Jeweler's Gem

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

Snug yet stylish, this studio apartment is perfect for a lone traveller or couple wanting a cosy stay in Chicago. We love the sleek design and jewel tones – fitting, seeing as this flat is situated along the famous Jewelers Row.

The Jeweller

The Jeweller

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

Just a block away from Millennium Park and the Art Institute of Chicago, this neat little apartment puts you in the centre of the Windy City. It’s a three-minute walk to Millennium Park where you’ll find fountains, playparks and sculptures, including the iconic Bean.

Diamonds Are Forever

Diamonds Are Forever

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

In an iconically Chicago building designed by Adler & Sullivan, this apartment sits amidst jewellery shops that have been trading since the 19th century and is just a couple of blocks from the sculpture-strewn Millennium Park. As well as old-world jewellery shops, contemporary galleries and trendy eateries fill the streets surrounding this apartment.

South Soul

South Soul

  • 2 guests

  • 1 bedrooms

South Loop, Chicago

Looking for a stylish bolthole in a buzzy pocket of Chicago? Then this smart studio apartment, located in the residential district of South Loop, might tick your boxes.


We selected the top 3% holiday homes in Cook County Holiday Rentals

Explore the 41 most perfect homes in our collection

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Most popular homes in Cook County

Skyscraper

Skyscraper

  • 3 guests

  • 1 bedrooms

Near North, Chicago

New Millennium

New Millennium

  • 4 guests

  • 2 bedrooms

Chicago Loop, Chicago

Loop In

Loop In

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

Drive Me Loopy

Drive Me Loopy

  • 4 guests

  • 1 bedrooms

South Loop, Chicago

Flaming Saganaki

Flaming Saganaki

  • 4 guests

  • 1 bedrooms

Greektown, Chicago

Indigo Wabash

Indigo Wabash

  • 4 guests

  • 2 bedrooms

Chicago Loop, Chicago

Running Loops

Running Loops

  • 6 guests

  • 3 bedrooms

South Loop, Chicago

Southern Loop

Southern Loop

  • 4 guests

  • 1 bedrooms

South Loop, Chicago

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Explore our selection of the finest luxury Holiday Rentals for your next getaway in Cook County, Illinois, United States. The homes in Plum Guide's collection come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Each home is professionally vetted and carefully handpicked, with both measurable and soft 'feel' elements thoroughly tested to ensure the highest quality. Book today and enjoy a short or extended stay in one of the best homes that Cook County, Illinois, United States has to offer. Our friendly experts are also on hand 24/7, should you need any help finding the perfect Holiday Rentals for your trip.

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