Darien Holiday Rentals
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Our top choices for Darien holiday rentals
Aparthotel in Downtown Chicago
Kasa River North Chicago9.6 out of 10, Exceptional, (182)
"Awesome stay "
Sally
Aparthotel in Downtown Chicago
Chicago luxury home suites10.0 out of 10, Exceptional, (4)
"Amazing stay! The location is very central and close to everything. The room was spotless, and the mattress was very comfortable. I really appreciated that the property is pet friendly. I was able to bring my dog along, which made the trip even better. The view was absolutely stunning. The hosts were very responsive and helpful throughout our stay. Highly recommend!"
Alex
The price is S$198
includes taxes & fees
30 Dec - 31 Dec
ENVITAE Hotel 4 Bedroom Luxury Apartments
ENVITAE Hotel 4 Bedroom Luxury Apartments10.0 out of 10, Exceptional, (8)
"We loved at our stay at this property. It was one of the best stays we have had on vacation."
Javeria
The price is S$859
includes taxes & fees
30 Dec - 31 Dec
Aparthotel in Downtown Chicago
Sentral Michigan Avenue9.2 out of 10, Wonderful, (1026)
"My favorite place to stay hands-down"
Michele
The price is S$216
includes taxes & fees
4 Jan - 5 Jan, 2026
Aparthotel in West Town
Chicago Third Floor Studio by 747 Lofts9.8 out of 10, Exceptional, (6)
"Cute little studio that was clean. There was a nice size kitchen and was close to our activities in the West loop of Chicago. There was also assistance with parking located in the lofts."
Jennifer
The price is S$286
includes taxes & fees
30 Dec - 31 Dec
Cottage in Forest Park
Classic Forest Park Foursquare < 1 Mi to Blue LineThe price is S$530
includes taxes & fees
1 Jan - 2 Jan, 2026
Holiday Home in Shorewood
Modern 4 Bedroom Private Vacation HomeThe price is S$801
includes taxes & fees
30 Dec - 31 Dec
Aparthotel in West Town
Cabin 105 by 747 Lofts10.0 out of 10, Exceptional, (1)
The price is S$170
includes taxes & fees
30 Dec - 31 Dec
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Darien Hotel Reviews
Silversmith Hotel Chicago Downtown
10/10 Excellent
