Darien Holiday Rentals

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Our top choices for Darien holiday rentals

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1005)
"Beautiful view, and a very nice condo. "
United States
Tiffanie
The price is AU$253
includes taxes & fees
21 Dec - 22 Dec
Sentral Michigan Avenue

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 AU$186
includes taxes & fees
11 Dec - 12 Dec
Chicago luxury home suites

Twice as Nice: Chic 2BR Stay with Style & Space

Twice as Nice: Chic 2BR Stay with Style & Space
Downtown Chicago
9.6 out of 10, Exceptional, (14)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
The price is AU$308
includes taxes & fees
11 Dec - 12 Dec
Twice as Nice: Chic 2BR Stay with Style & Space

Modern West Loop Gem-City Views & Prime Location 5

Modern West Loop Gem-City Views & Prime Location 5
2.0 star property
Downtown Chicago
8.0 out of 10, Very good, (1)
"Great location, plenty of space and clean home. "
United States
Brittany T.
The price is AU$485
includes taxes & fees
17 Dec - 18 Dec
Modern West Loop Gem-City Views & Prime Location 5

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is AU$257
includes taxes & fees
1 Jan - 2 Jan 2026
1BR Modern Luxe Apt with In-Unit Laundry

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (181)
"Awesome stay "
United States
Sally
Kasa River North Chicago

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (3)
"Pretty cool place to stay for a short trip ! Everything was close to where we were which made traveling a lot easier. Apartment is a pretty decent size I would recommend just 2-3 people. You can easily contact the host about anything and they’ll respond within a timely manner. The only down side of this place was the shower cleanliness itself. Overall, cool place not bad at all definitely a quick trip kind of thing!"
United States
Majanique M.
The price is AU$257
includes taxes & fees
4 Jan - 5 Jan 2026
West Loop Living – Bright 1BR

Downtown Chicago Stay with Free In & Out Parking 3

Downtown Chicago Stay with Free In & Out Parking 3
2.0 star property
Downtown Chicago
The price is AU$484
includes taxes & fees
17 Dec - 18 Dec
Downtown Chicago Stay with Free In & Out Parking 3

Stylish 1BR in West Loop

Stylish 1BR in West Loop
Downtown Chicago
10.0 out of 10, Exceptional, (10)
"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"
United States
Jacob D.
The price is AU$257
includes taxes & fees
1 Jan - 2 Jan 2026
Stylish 1BR in West Loop

Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment
Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is AU$257
includes taxes & fees
1 Jan - 2 Jan 2026
Sun-Drenched 1BR Apartment

South Loop Rooftop With In & Out Parking 1

South Loop Rooftop With In & Out Parking 1
Downtown Chicago
9.0 out of 10, Wonderful, (2)
"We loved the property! It was well kept, clean, with a seamless check in and check out process! I wish the parking garage would have been closer but otherwise everything was great! Shout out to the host for his promptness with all my questions! I would recommend this place if they are looking for a place to stay! "
United States
Bridney K.
The price is AU$484
includes taxes & fees
8 Jan - 9 Jan 2026
South Loop Rooftop With In & Out Parking 1

The One: A 1BR Stay That Feels Like Home

The One: A 1BR Stay That Feels Like Home
Downtown Chicago
9.6 out of 10, Exceptional, (4)
"Convenient location and clean place"
United States
David S.
The price is AU$257
includes taxes & fees
1 Jan - 2 Jan 2026
The One: A 1BR Stay That Feels Like Home

Your Chicago get Away

Your Chicago get Away
Downtown Chicago
8.4 out of 10, Very good, (8)
"Clean, simple space close to the parks at the waterfront (Millennium, Grant, etc) and several spots for coffee. A bit of an odd building location (it's in a dorm tower with a laundry space next door! Not noisy tho) but easy to access at all hours, nice view as pictured."
United States
Pip M.
The price is AU$622
includes taxes & fees
11 Dec - 12 Dec
Your Chicago get Away

Modern 2BR Retreat Near Old Town & Lincoln Park

Modern 2BR Retreat Near Old Town & Lincoln Park
Near North Side
9.6 out of 10, Exceptional, (4)
"Had a great stay here - wonderful apartment and great location! Host was awesome and apartment was stocked super well and clean. Will absolutely stay here again! "
United States
Jackie L.
The price is AU$692
includes taxes & fees
12 Dec - 13 Dec
Modern 2BR Retreat Near Old Town & Lincoln Park

Modern West Loop Gem-City Views & Prime Location 4

Modern West Loop Gem-City Views & Prime Location 4
2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Amazing accommodation"
United States
Jiri N.
The price is AU$563
includes taxes & fees
22 Dec - 23 Dec
Modern West Loop Gem-City Views & Prime Location 4

Sleek 1BR Apt w/ Laundry

Sleek 1BR Apt w/ Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."
United States
Anonymous traveller
The price is AU$257
includes taxes & fees
4 Jan - 5 Jan 2026
Sleek 1BR Apt w/ Laundry

Modern West Loop Gem-City Views & Prime Location 3

Modern West Loop Gem-City Views & Prime Location 3
2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"The host communicated everything very well. The short videos sent giving info about all the things you'd need to know were super helpful!"
United States
Laurie A.
The price is AU$584
includes taxes & fees
18 Dec - 19 Dec
Modern West Loop Gem-City Views & Prime Location 3

Modern West Loop Gem-City Views & Prime Location 2

Modern West Loop Gem-City Views & Prime Location 2
2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Apartment was clean and nice. Nice to have off street parking and the hosts were quick to respond. "
United States
Erik R.
The price is AU$634
includes taxes & fees
30 Dec - 31 Dec
Modern West Loop Gem-City Views & Prime Location 2

River North Private Deck With In and Out Parking

River North Private Deck With In and Out Parking
Downtown Chicago
10.0 out of 10, Exceptional, (3)
"The property was exactly as advertised; clean, good neighborhood, and the views of the city were great. The private outdoor patio access was fantastic."
United States
Rich G.
The price is AU$1,093
includes taxes & fees
26 Dec - 27 Dec
River North Private Deck With In and Out Parking

Complete 1BR Home Sum

Complete 1BR Home Sum
Downtown Chicago
The price is AU$257
includes taxes & fees
1 Jan - 2 Jan 2026
Complete 1BR Home Sum
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

Find out more about Darien

Everything you need to know about Darien holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Darien holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Darien holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Darien holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Darien. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Darien holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Darien holiday rentals we have selected for you start as low as AU$186 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Darien rentals

At Expedia, we put the best Darien holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Darien rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Darien holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Darien. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

NEW to the market! Relax with family in a super Lux Custom SFH. West town.: This holiday home rental outside of Darien offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a garden.

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.