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Check prices for these dates

Tonight
11 Dec - 12 Dec
Tomorrow
12 Dec - 13 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

Our top choices for Darien holiday rentals

Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1006)
"Beautiful view, and a very nice condo. "
United States
Tiffanie
The price is ₹10,629
₹15,117 total
includes taxes & fees
21 Dec - 22 Dec
Sentral Michigan Avenue
Exterior
Kasa South Loop Chicago

Kasa South Loop Chicago

Kasa South Loop Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (386)
"Great apartment, great view, close to good amenities, very safe."
United Kingdom
Ian
Kasa South Loop Chicago
Fridge, microwave, oven, stovetop
Chicago luxury home suites

Chicago luxury home suites

Chicago luxury home suites
2.0 star property
Downtown Chicago
7.4 out of 10, Good, (3)
"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 ₹11,841
₹13,901 total
includes taxes & fees
14 Dec - 15 Dec
Chicago luxury home suites
50-inch Smart TV with satellite channels
The Neighborhood Hotel-Little Italy

The Neighborhood Hotel-Little Italy

The Neighborhood Hotel-Little Italy
4.0 star property
Near West Side
9.6 out of 10, Exceptional, (224)
"great place- excellent rooms and near tons of dining "
United States
chris
The Neighborhood Hotel-Little Italy
Lounge
Kasa River North Chicago

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (182)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Classic Apartment | Private kitchen
Stylish Apartment near Chicago Downtown

Stylish Apartment near Chicago Downtown

Stylish Apartment near Chicago Downtown
2.0 star property
Bridgeport
The price is ₹2,748
₹20,283 total
includes taxes & fees
10 Jan - 11 Jan 2026
Stylish Apartment near Chicago Downtown
Design Townhome, 3 Bedrooms, Kitchen, City View | Terrace/patio
Art Villa

Art Villa

Art Villa
5.0 star property
West Town
10.0 out of 10, Exceptional, (2)
Art Villa
Front of property
Modern 4 Bedroom Private Vacation Home

Modern 4 Bedroom Private Vacation Home

Modern 4 Bedroom Private Vacation Home
2.5 star property
Shorewood
The price is ₹44,492
₹56,097 total
includes taxes & fees
14 Dec - 15 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

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) | Lounge
Historic Oak Park Home

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
Front of property
Logan Square SRO Hotel

Logan Square SRO Hotel

Logan Square SRO Hotel
2.0 star property
Logan Square
Logan Square SRO Hotel
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

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent
"Lovely hotel."
Cedrick 2-night trip
Posted 22 hours ago
Crowne Plaza Chicago West Loop by IHG

Find out more about Darien

Holiday Rentals in Darien

Search for holiday rentals in Darien on Expedia.co.uk! 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.