Darien Vacation Rentals

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Check prices for these dates

Tonight
29 Dec - 30 Dec
Tomorrow
30 Dec - 31 Dec
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Darien holiday rentals

Business centre
Kasa River North Chicago

Aparthotel in Downtown Chicago

Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (182)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Front of property
Chicago luxury home suites

Aparthotel in Downtown Chicago

Chicago luxury home suites
2.0 star property
10.0 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!"
Canada
Alex
The price is RM547
RM642 total
includes taxes & fees
30 Dec - 31 Dec
Chicago luxury home suites
Private kitchen
ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments
2.0 star property
10.0 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."
United States
Javeria
The price is RM1,425
RM2,524 total
includes taxes & fees
30 Dec - 31 Dec
ENVITAE Hotel 4 Bedroom Luxury Apartments
Indoor pool
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (1026)
"My favorite place to stay hands-down"
United States
Michele
The price is RM479
RM681 total
includes taxes & fees
4 Jan - 5 Jan 2026
Sentral Michigan Avenue
Exterior
Chicago Third Floor Studio by 747 Lofts

Aparthotel in West Town

Chicago Third Floor Studio by 747 Lofts
2.0 star property
9.8 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."
United States
Jennifer
The price is RM252
RM902 total
includes taxes & fees
30 Dec - 31 Dec
Chicago Third Floor Studio by 747 Lofts
Interior
Classic Forest Park Foursquare < 1 Mi to Blue Line

Cottage in Forest Park

Classic Forest Park Foursquare < 1 Mi to Blue Line
3.0 star property
The price is RM640
RM1,671 total
includes taxes & fees
1 Jan - 2 Jan 2026
Classic Forest Park Foursquare < 1 Mi to Blue Line
Terrace/patio
Modern 4 Bedroom Private Vacation Home

Holiday Home in Shorewood

Modern 4 Bedroom Private Vacation Home
2.5 star property
The price is RM2,005
RM2,528 total
includes taxes & fees
30 Dec - 31 Dec
Modern 4 Bedroom Private Vacation Home
Exterior
Cabin 105 by 747 Lofts

Aparthotel in West Town

Cabin 105 by 747 Lofts
2.0 star property
10.0 out of 10, Exceptional, (1)
The price is RM236
RM537 total
includes taxes & fees
30 Dec - 31 Dec
Cabin 105 by 747 Lofts
Exterior
Ground Floor Studios in Chicago by 747 Lofts

Aparthotel in West Town

Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
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
The price is RM236
RM880 total
includes taxes & fees
30 Dec - 31 Dec
Ground Floor Studios in Chicago by 747 Lofts
Exterior
River West, Second Floor Chicago by 747 Lofts

Aparthotel in West Town

River West, Second Floor Chicago by 747 Lofts
2.0 star property
9.6 out of 10, Exceptional, (4)
"I need to somewhere to stay for a night in Chicago and found this place. It had a varying level of reviews but found the property more the suitable for what I paid. Easy to follow instructions to get in, clean, and convienent. They even provide ear plugs to drown out the sounds of the city."
United States
Anonymous traveller
The price is RM244
RM891 total
includes taxes & fees
1 Jan - 2 Jan 2026
River West, Second Floor Chicago by 747 Lofts
Private kitchen
Chicago Second Floor Studio by 747 Lofts

Aparthotel in West Town

Chicago Second Floor Studio by 747 Lofts
2.0 star property
8.8 out of 10, Excellent, (13)
"Great location, convenient to downtown and blue line to airport. Everything necessary in unit, comfortable temperature and full kitchen with unique grocery store nearby."
United States
Barbara
The price is RM236
RM537 total
includes taxes & fees
12 Jan - 13 Jan 2026
Chicago Second Floor Studio by 747 Lofts
Interior
Fire Pit & Grill: Family Home on Fox River Trail!

Cottage in St. Charles

Fire Pit & Grill: Family Home on Fox River Trail!
3.0 star property
The price is RM741
RM2,190 total
includes taxes & fees
4 Jan - 5 Jan 2026
Fire Pit & Grill: Family Home on Fox River Trail!
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

Pendry Chicago

Pendry Chicago

10/10 Excellent
"A very clean room, everything smells good and fresh, very nice staff, the staff helps all the time, my family and I feels very secure in the hotel."
Raúl 3-night trip
Posted 2 days ago
Pendry Chicago

Find out more about 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.

What are some of the best holiday rentals that Darien has to offer?

Modern 4 Bedroom Private Vacation Home : This holiday home rental outside of Darien offers a BBQ and free WiFi to help you feel comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals are there in Darien?

Choose from 7 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 Morton Arboretum. 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.