Book Luxury Holiday Rentals in Illinois

Award-winning homes from £98

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Age 13+

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Age 1 to 12

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Home spotlights in Illinois

Stars of Wonder

Stars of Wonder

  • 12 guests

  • 4 bedrooms

Highland Heights, Nashville

A stay in this home promises to bring you a healthy dose of fun. There’s an expansive rooftop deck with incredible skyline views and a bar for magical sunset drinks.

Song of the Heart

Song of the Heart

  • 12 guests

  • 4 bedrooms

FANG, Nashville

If you’re feeling called by the musical spirit of Nashville, this home delivers a sweet solution. From the private backyard with a fire pit and barbecue to the rooftop lounge, you’ll find everything you could need for a refreshing city break.

Southern Charm Haven

Southern Charm Haven

  • 5 guests

  • 2 bedrooms

Edgehill, Nashville

For a vibrant stay in the heart of Nashville, this cosy bungalow couldn’t be better placed. It’s less than two miles to the iconic Broadway and you can stroll to 12 South where you’ll find great restaurants, bars and boutiques.

Chicago Morning

Chicago Morning

  • 8 guests

  • 4 bedrooms

Printer's Row, Chicago

Initially designed by an architect for their family, this incredible Chicago condo has been featured in magazines and even TV commercials. Located in the heart of downtown Chicago, this home is central to the sights and activities of the area, and also boasts an incredible green, real grass rooftop terrace with views that span across the south, east, and west of the city.


We selected the top 3% holiday homes in Illinois Holiday Rentals

Explore the 104 most perfect homes in our collection

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Most popular homes in Illinois

Chicago Chill Pad

Chicago Chill Pad

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

Be the Music

Be the Music

  • 12 guests

  • 4 bedrooms

McKissack Park, Nashville

Heart of Nashville

Heart of Nashville

  • 11 guests

  • 4 bedrooms

West End Park, Nashville

Nashville Nook

Nashville Nook

  • 4 guests

  • 2 bedrooms

Edgehill, Nashville

Southern Serenade

Southern Serenade

  • 12 guests

  • 5 bedrooms

Edgehill, Nashville

Chicago Charisma

Chicago Charisma

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

All Things Glow

All Things Glow

  • 3 guests

  • 2 bedrooms

Hyde Park, Chicago

Luxury & Adventure Haven

Luxury & Adventure Haven

  • 12 guests

  • 4 bedrooms

Edgehill, Nashville

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Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in 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 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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