Darien Holiday Rentals

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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Darien holiday rentals

TV, offices

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
9.0 out of 10, Wonderful, (17 reviews)
"Great location, apt well equipped and host very responsive. Wonderful stay. "
United States
Gina G.
The price is HK$564
HK$1,402 total
includes taxes & fees
19 Apr - 20 Apr
Modern Comfort: 1BR Unit w/ Laundry
Interior

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.6 out of 10, Exceptional, (5 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
The price is HK$1,252
HK$3,554 total
includes taxes & fees
29 Apr - 30 Apr
River North Rooftop With In and Out Parking 3
1 bedroom, iron/ironing board, travel cot, WiFi

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (9 reviews)
"Great spot next to the green line train a few restaurants and a Starbucks right up the street I will book again for sure "
United States
2k G.
The price is HK$884
HK$1,825 total
includes taxes & fees
21 Apr - 22 Apr
West Loop Living – Bright 1BR
TV, offices

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"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 HK$884
HK$1,825 total
includes taxes & fees
26 Apr - 27 Apr
Sunlit 1BR Apartment | Warm & Welcoming Space
Exterior

Envitae Hotel, 4BR Modern Sleek Apartment

Envitae Hotel, 4BR Modern Sleek Apartment
Near North Side
The price is HK$1,330
HK$3,834 total
includes taxes & fees
13 May - 14 May
Envitae Hotel, 4BR Modern Sleek Apartment
Fridge, microwave, oven, stovetop

Cozy Boho Chicago - 10 Minutes to Downtown Chicago

Cozy Boho Chicago - 10 Minutes to Downtown Chicago
Lawndale
9.8 out of 10, Exceptional, (10 reviews)
"Wonderful space and convenient location. Really responsive host and super quiet neighborhood! "
United States
Jess S.
Cozy Boho Chicago - 10 Minutes to Downtown Chicago
Interior

Modern West Loop Gem-City Views & Prime Location 3

Modern West Loop Gem-City Views & Prime Location 3
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"Loved the place 4 bedroom & 4 bathrooms was ideal for our stayGreat locationLoved the well stocked convenience store a block away "
United States
Tina Y.
Modern West Loop Gem-City Views & Prime Location 3
Exterior

A quiet stay while you are away

A quiet stay while you are away
Oak Park
9.8 out of 10, Exceptional, (36 reviews)
"Everything was very comfortable and Jay did a great job of showing the house. I would definitely come back again"
United States
Fred D.
The price is HK$754
HK$1,857 total
includes taxes & fees
20 Apr - 21 Apr
A quiet stay while you are away
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,130 reviews)
"Clean spacious my go to vacation spot all year around "
United States
xavier
The price is HK$1,124
HK$1,549 total
includes taxes & fees
26 Apr - 27 Apr
Sentral Michigan Avenue
1 bedroom, iron/ironing board, travel cot, WiFi

LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"The service was top notch at this property. The hosts were super responsive and professional. The location was incredible. Loved being able to cook in the apartment. The apartment was newly renovated and very urban chic. "
United States
Michelle R.
The price is HK$1,080
HK$1,461 total
includes taxes & fees
26 Apr - 27 Apr
LIVN West Loop Chicago Queen Superior Studio
1 bedroom, iron/ironing board, travel cot, WiFi

Charming Sunlit 1BR Apartment

Charming Sunlit 1BR Apartment
Irving Park
9.0 out of 10, Wonderful, (14 reviews)
"Host was very attentive and answered all of our questions. It was very cozy and exactly as pictured."
United States
Brandon M.
The price is HK$704
HK$1,566 total
includes taxes & fees
27 Apr - 28 Apr
Charming Sunlit 1BR Apartment
Iron/ironing board, travel cot, WiFi, bed sheets

Cozy Charm Studio Apt in Chicago

Cozy Charm Studio Apt in Chicago
Hyde Park
10.0 out of 10, Exceptional, (7 reviews)
"Room was clean, check in was easy, and the owner was very communicative."
United States
David
The price is HK$689
HK$1,469 total
includes taxes & fees
22 Apr - 23 Apr
Cozy Charm Studio Apt in Chicago
Iron/ironing board, travel cot, WiFi, bed sheets

Modern Studio Unit Near UChicago

Modern Studio Unit Near UChicago
Hyde Park
9.0 out of 10, Wonderful, (18 reviews)
"Clean room and convenient location! "
United States
Gabriela
The price is HK$736
HK$1,524 total
includes taxes & fees
22 Apr - 23 Apr
Modern Studio Unit Near UChicago
Interior

Your Perfect 2BR Home

Your Perfect 2BR Home
Near West Side
8.4 out of 10, Very good, (15 reviews)
"Great location! "
United States
Kourtney K.
The price is HK$665
HK$1,677 total
includes taxes & fees
21 Apr - 22 Apr
Your Perfect 2BR Home
Fridge, microwave, oven, stovetop

Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (73 reviews)
"Apartment is as advertised. Nicely stocked, large, clean, comfortable, nice natural light, quiet, great location, full size appliances, easy access. "
United States
Susan G.
The price is HK$845
HK$2,267 total
includes taxes & fees
28 Apr - 29 Apr
Cozy, Comfortable and Convenient apartment. Close to everything!
Property grounds

Pet Friendly-Cozy 1-bedroom apartment just 6 minutes drive to Morton Arboretum

Pet Friendly-Cozy 1-bedroom apartment just 6 minutes drive to Morton Arboretum
Downers Grove
9.6 out of 10, Exceptional, (33 reviews)
"Great option for a relatively affordable place to stay near family."
United States
Erick B.
The price is HK$569
HK$976 total
includes taxes & fees
25 Apr - 26 Apr
Pet Friendly-Cozy 1-bedroom apartment just 6 minutes drive to Morton Arboretum
Interior

Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
Northlake
10.0 out of 10, Exceptional, (11 reviews)
"Had a great experience here, and also close to the airport!"
United States
Yafeat D.
The price is HK$743
HK$963 total
includes taxes & fees
20 Apr - 21 Apr
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
Fridge, microwave, oven, stovetop

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Worth
9.4 out of 10, Exceptional, (60 reviews)
"Home was exactly what we were needing fir our stay. Host was responsive and timely. "
United States
Stephanie H.
The price is HK$1,096
HK$2,467 total
includes taxes & fees
20 Apr - 21 Apr
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
1 bedroom, WiFi, bed sheets

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
8.0 out of 10, Very good, (2 reviews)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is HK$885
HK$1,827 total
includes taxes & fees
19 Apr - 20 Apr
1BR Modern Luxe Apt with In-Unit Laundry
Smart TV, books

Chic Suite/Mins to L Train /Laundry/Free Parking

Chic Suite/Mins to L Train /Laundry/Free Parking
Oak Park
9.6 out of 10, Exceptional, (61 reviews)
"Comfortable bed, spacious rooms and clean."
United States
Michael W.
The price is HK$861
HK$1,962 total
includes taxes & fees
18 May - 19 May
Chic Suite/Mins to L Train /Laundry/Free Parking
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

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

10/10 Excellent
"Best view ever "
daniela 1-night trip
Posted 3 hours ago
Hilton Garden Inn Chicago Downtown South Loop

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!

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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?

HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony: This holiday home rental outside of Darien is located in the city centre, and has a balcony, an arcade/games room and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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.