Culture Haven
12 guests
4 bedrooms
Rush & Division, Chicago
Welcome to The Hermes! Nestled in the vibrant Streeterville neighborhood, classic charm meets culture and bustling downtown lifestyle in the heart of The Windy City.
Streeterville Holiday Homes with Staff
We selected the 10 homes worth renting in this location
Home spotlights in Streeterville
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.
Chicago Charisma
5 guests
2 bedrooms
Chicago Loop, Chicago
Immerse yourself in the heart of downtown at this retreat tucked away in Chicago's vibrant Financial District. Each experience here invites a journey into iconic city attractions, folds back layers of historic architectural treasures, and strolls along river cruises or the fabled Riverwalk.
We selected the top 3% holiday homes in Streeterville Holiday Homes with Staff
Explore the 10 most perfect homes in our collection
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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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