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Streeterville Holiday Homes with Staff

We selected the 46 homes worth renting in this location

Who's coming along?

Adults

Age 13+

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Children

Age 1 to 12

0

Infants

Under 1

0

Pets

An extra fee may apply

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Home spotlights in Streeterville

Easel And Brush

Easel And Brush

  • 5 guests

  • 2 bedrooms

Near North, Chicago

If you’re visiting Chicago and you're interested in art, then the chic River North neighbourhood is the perfect place to stay. The area is now the city’s art and design quarter, with the highest concentration of galleries in the US after Manhattan.

Gilded Frame

Gilded Frame

  • 3 guests

  • 1 bedrooms

Near North, Chicago

If you’re an art lover looking to visit Chicago, then you’ve come to the right place. River North, where this delightful one-bedroom is located, has the highest concentration of galleries in the US, after Manhattan.

On Cloud Nine

On Cloud Nine

  • 2 guests

  • 1 bedrooms

Near North, Chicago

Chicago isn't just known for its lively music scene and deep-dish pizza, but also for its larger-than-life architecture – after all, those skyscrapers speak for themselves. The best way to make the most of the magnificent metropolis?

Monday Night

Monday Night

  • 3 guests

  • 1 bedrooms

South Loop, Chicago

Convenience is key at this stylish apartment in Chicago’s trendy River North neighbourhood. From the moment you wake up in your plush, king-size bed you'll take in sprawling city views from the floor-to-ceiling windows.

We selected the top 3% holiday homes in Streeterville Holiday Homes with Staff

Explore the 46 most perfect homes in our collection

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Most popular homes in Streeterville

Panorama Place

Panorama Place

  • 6 guests

  • 3 bedrooms

South Loop, Chicago

Local Colour

Local Colour

  • 4 guests

  • 2 bedrooms

Near North, Chicago

Savings Account

Savings Account

  • 3 guests

  • 1 bedrooms

Near North, Chicago

Skyscraper

Skyscraper

  • 3 guests

  • 1 bedrooms

Near North, Chicago

Checking Account

Checking Account

  • 2 guests

  • 1 bedrooms

Near North, Chicago

Solo Bird

Solo Bird

  • 2 guests

  • 1 bedrooms

Near North, Chicago

Modern Dream

Modern Dream

  • 3 guests

  • 1 bedrooms

Near North, Chicago

River Style

River Style

  • 5 guests

  • 2 bedrooms

Near North, Chicago

View all

Check upcoming rates & availability for Streeterville Holiday Homes with Staff

Frequently asked questions

Are you hoping for a stay in one of the best holiday homes with staff in Streeterville? If so, you've definitely come to the right place. Reach out to our expert team who will happily arrange for staff to be present at your home in Streeterville as an addition to your booking. Our Plum Guide homes come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Book today and enjoy a short extended stay. Should you need anything, our friendly team is on hand 24/7, so just ask.

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