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Check prices for these dates

In two weeks
12 Dec - 14 Dec
In two months
23 Jan - 25 Jan
In three months
20 Feb - 22 Feb
In four months
20 Mar - 22 Mar

Top Holiday Rentals in Darien

Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (997)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is ฿3,236
฿4,741 total
includes taxes & fees
7 Dec - 8 Dec
Sentral Michigan Avenue
Deluxe Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | Balcony
Kasa South Loop Chicago

Kasa South Loop Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (377)
"An excellent place to stay in Chicago downtown."
United States
ABDULHAFEEZ
Kasa South Loop Chicago
Front of property
The Neighborhood Hotel-Little Italy

The Neighborhood Hotel-Little Italy

4.0 star property
Near West Side
9.6 out of 10, Exceptional, (221)
"Staff was courteous. Great location."
United States
Pamela
The Neighborhood Hotel-Little Italy
Free WiFi, bed sheets
Chicago luxury home suites

Chicago luxury home suites

2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job."
Canada
pouya
The price is ฿7,514
฿8,820 total
includes taxes & fees
30 Nov - 1 Dec
Chicago luxury home suites
Business centre
Kasa River North Chicago

Kasa River North Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (180)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Classic Apartment | Private kitchen
Stylish Apartment near Chicago Downtown

Stylish Apartment near Chicago Downtown

2.0 star property
Bridgeport
The price is ฿7,995
฿12,703 total
includes taxes & fees
1 Dec - 2 Dec
Stylish Apartment near Chicago Downtown
Interior
Art Villa

Art Villa

5.0 star property
West Town
10.0 out of 10, Exceptional, (2)
" "
United States
tomonobu
Art Villa
Family House, 4 Bedrooms | Terrace/patio
Modern 4 Bedroom Private Vacation Home

Modern 4 Bedroom Private Vacation Home

2.5 star property
Shorewood
The price is ฿15,894
฿20,040 total
includes taxes & fees
30 Nov - 1 Dec
Modern 4 Bedroom Private Vacation Home
Studio | Exterior
Ground Floor Studios in Chicago by 747 Lofts

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
West Town
9.0 out of 10, Wonderful, (21)
"The stay lacked in shelf space as well as other amenities that could be useful. "
United States
Zugeily
Ground Floor Studios in Chicago by 747 Lofts
Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Interior
Historic Oak Park Home

Historic Oak Park Home

2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
Historic Oak Park Home
Studio | Private kitchen | Fridge, oven, coffee/tea maker, toaster
River West, Third Floor Chicago by 747 Lofts

River West, Third Floor Chicago by 747 Lofts

2.0 star property
West Town
9.0 out of 10, Wonderful, (17)
"Overall solid property, I will return."
United States
Fletcher
River West, Third Floor Chicago by 747 Lofts
Family Apartment, Multiple Beds, Lake View | Private kitchen | Fridge, microwave, oven, stovetop
Warrenville Rep 2

Warrenville Rep 2

4.0 star property
Warrenville
10.0 out of 10, Exceptional, (1)
"This was a four bedroom townhome, fully furnished, with all linens and a full kitchen with ample supplies. It was clean and bright, and simply but pleasantly furnished. There are two large bedrooms, one mid-sized, and one smaller. The first floor is the kitchen and living room and a half bath. The second has a three bedrooms and two full baths. The third floor has another large bedroom with a balcony and a half bath (and a ping pong table!). Do note that if you are reserving through...
United States
Cheryl
Warrenville Rep 2
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

citizenM Chicago Downtown

citizenM Chicago Downtown

10/10 Excellent
"Everything was Amazing "
Eto 1-night trip
Posted 1 day ago
citizenM Chicago Downtown

Find out more about Darien

Search for holiday rentals in Darien on Expedia! You can easily find your home rentals, villas, holiday apartments in Darien using one of the methods below:

  • View our selection of featured holiday rentals in Darien
  • Use the map to find apartments and other holiday homes in the Darien neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Darien while they last

Look no further and take a look at our great range of rental properties in Darien!

Frequently asked questions

Can I find a holiday rental in Darien?

Yes, there are holiday rentals close to the most popular sights in Darien, or you can select a more secluded option if you're looking for a relaxing stay. Darien is known for its temples and shopping. Make sure you have time to check out the restaurants and basketball games during your trip.

How many holiday rentals are there in Darien?

Choose from 8 Expedia holiday rentals in Darien for a memorable holiday.

What can I see and do in Darien?

While exploring the area, visit family-friendly sights like Galloping Ghost, or get outside and enjoy nature at Ty Warner Park. In the wider area, you’ll find National Shrine of St. Therese and Burr Ridge Village Center.

What are holiday rentals like in Darien?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Darien. Holiday rentals provide amenities such as patios, hot tubs and fire pits so your stay will be comfortable. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for family trips or small group gatherings.