Darien Vacation Rentals

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Check prices for these dates

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

Our top choices for Darien vacation rentals

Business center
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
Front of property
Chicago luxury home suites

Chicago luxury home suites

Chicago luxury home suites
2.0 star property
Downtown Chicago
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 ₩194,624
₩228,469 total
includes taxes & fees
Dec 30 - Dec 31
Chicago luxury home suites
Business Apartment, City View | Private kitchen | Fridge, microwave, oven, stovetop
ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments
2.0 star property
Near North Side
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 ₩507,320
₩898,474 total
includes taxes & fees
Dec 30 - Dec 31
ENVITAE Hotel 4 Bedroom Luxury Apartments
Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1026)
"My favorite place to stay hands-down"
United States
Michele
The price is ₩170,344
₩242,277 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Sentral Michigan Avenue
Studio | Exterior
Chicago Third Floor Studio by 747 Lofts

Chicago Third Floor Studio by 747 Lofts

Chicago Third Floor Studio by 747 Lofts
2.0 star property
West Town
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 ₩89,787
₩321,073 total
includes taxes & fees
Dec 30 - Dec 31
Chicago Third Floor Studio by 747 Lofts
House (3 Bedrooms) | Interior
Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line
3.0 star property
Forest Park
The price is ₩227,782
₩594,670 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Classic Forest Park Foursquare < 1 Mi to Blue Line
Family House, 4 Bedrooms | Terrace/patio
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 ₩713,622
₩899,741 total
includes taxes & fees
Dec 30 - Dec 31
Modern 4 Bedroom Private Vacation Home
Studio | Exterior
Cabin 105 by 747 Lofts

Cabin 105 by 747 Lofts

Cabin 105 by 747 Lofts
2.0 star property
West Town
10.0 out of 10, Exceptional, (1)
The price is ₩83,962
₩191,294 total
includes taxes & fees
Dec 30 - Dec 31
Cabin 105 by 747 Lofts
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
The price is ₩83,962
₩313,272 total
includes taxes & fees
Dec 30 - Dec 31
Ground Floor Studios in Chicago by 747 Lofts
Studio | Exterior
River West, Second Floor Chicago by 747 Lofts

River West, Second Floor Chicago by 747 Lofts

River West, Second Floor Chicago by 747 Lofts
2.0 star property
West Town
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 traveler
The price is ₩86,874
₩317,194 total
includes taxes & fees
Jan 1 - Jan 2, 2026
River West, Second Floor Chicago by 747 Lofts
Studio | Private kitchen | Fridge, oven, coffee/tea maker, toaster
Chicago Second Floor Studio by 747 Lofts

Chicago Second Floor Studio by 747 Lofts

Chicago Second Floor Studio by 747 Lofts
2.0 star property
West Town
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 ₩83,962
₩191,294 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Chicago Second Floor Studio by 747 Lofts
House (3 Bedrooms) | Interior
Fire Pit & Grill: Family Home on Fox River Trail!

Fire Pit & Grill: Family Home on Fox River Trail!

Fire Pit & Grill: Family Home on Fox River Trail!
3.0 star property
St. Charles
The price is ₩263,824
₩779,434 total
includes taxes & fees
Jan 4 - Jan 5, 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

Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

10/10 Excellent
"Great hotel"
Eric 2-night trip
Posted 2 hours ago
Holiday Inn Chicago Dwtn - The Mart by IHG

Find out more about Darien

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

  • View our selection of featured Vacation rentals in Darien
  • Use the map to find apartments and other Vacation homes in the Darien neighbourhood you prefer
  • Enter your travel dates to view the best deals on Vacation 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 vacation rental in Darien?

Yes, we give you a choice of vacation rentals close to top local attractions in Darien, or you can go with a secluded option if you want a relaxing place to 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's the top vacation rental in Darien?

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

How many vacation rentals are there in Darien?

Choose from 7 Expedia vacation rentals in Darien for a memorable vacation.

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 larger area, you’ll find National Shrine of St. Therese and Burr Ridge Village Center.

What are vacation rentals like in Darien?

Vacation rentals are private accommodations you can reserve for a few days or a quick weekend in Darien. Vacation rentals feature extras such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from shared hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for a family trip.