Darien Holiday Rentals

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Check prices for these dates

In two weeks
23 Jan - 25 Jan
In two months
6 Mar - 8 Mar
In three months
3 Apr - 5 Apr
In four months
1 May - 3 May

Our top choices for Darien holiday rentals

Indoor pool
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (1,039 reviews)
"Place was very nice and clean. We enjoyed the stay there. Will book it again when we come back to Chicago visit again. "
United States
Khalid
The price is HK$855
HK$1,232 total
includes taxes & fees
12 Jan - 13 Jan
Sentral Michigan Avenue
Lounge
Kasa River North Chicago

Aparthotel in Downtown Chicago

Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (183 reviews)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Interior
Twice as Nice: Chic 2BR Stay with Style & Space

Apartment in Downtown Chicago

Twice as Nice: Chic 2BR Stay with Style & Space
9.6 out of 10, Exceptional, (20 reviews)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
The price is HK$538
HK$1,485 total
includes taxes & fees
14 Jan - 15 Jan
Twice as Nice: Chic 2BR Stay with Style & Space
TV, offices
Sun-Drenched 1BR Apartment

Apartment in Downtown Chicago

Sun-Drenched 1BR Apartment
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$491
HK$1,313 total
includes taxes & fees
19 Jan - 20 Jan
Sun-Drenched 1BR Apartment
TV, offices
Modern Comfort: 1BR Unit w/ Laundry

Apartment in Downtown Chicago

Modern Comfort: 1BR Unit w/ Laundry
9.8 out of 10, Exceptional, (11 reviews)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is HK$491
HK$1,313 total
includes taxes & fees
12 Jan - 13 Jan
Modern Comfort: 1BR Unit w/ Laundry
1 bedroom, WiFi, bed sheets
1BR Modern Luxe Apt with In-Unit Laundry

Apartment in Downtown Chicago

1BR Modern Luxe Apt with In-Unit Laundry
10.0 out of 10, Exceptional, (1 review)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is HK$491
HK$1,313 total
includes taxes & fees
12 Jan - 13 Jan
1BR Modern Luxe Apt with In-Unit Laundry
1 bedroom, iron/ironing board, travel cot, WiFi
West Loop Living – Bright 1BR

Apartment in Downtown Chicago

West Loop Living – Bright 1BR
10.0 out of 10, Exceptional, (6 reviews)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
The price is HK$491
HK$1,313 total
includes taxes & fees
12 Jan - 13 Jan
West Loop Living – Bright 1BR
TV, offices
The One: A 1BR Stay That Feels Like Home

Apartment in Downtown Chicago

The One: A 1BR Stay That Feels Like Home
8.4 out of 10, Very good, (5 reviews)
"Very nice condo in a quiet neighborhood"
Canada
Patrick
The price is HK$491
HK$1,313 total
includes taxes & fees
15 Jan - 16 Jan
The One: A 1BR Stay That Feels Like Home
TV, offices
Chicago-Themed 1BR in a Central Spot near Downtown

Apartment in Downtown Chicago

Chicago-Themed 1BR in a Central Spot near Downtown
2.0 star property
The price is HK$491
HK$1,313 total
includes taxes & fees
13 Jan - 14 Jan
Chicago-Themed 1BR in a Central Spot near Downtown
Interior
River North Rooftop With In and Out Parking 3

Apartment in Downtown Chicago

River North Rooftop With In and Out Parking 3
9.6 out of 10, Exceptional, (4 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$779
HK$2,439 total
includes taxes & fees
13 Jan - 14 Jan
River North Rooftop With In and Out Parking 3
Fridge, microwave, oven, stovetop
Sleek 1BR Apt w/ Laundry

Apartment in Downtown Chicago

Sleek 1BR Apt w/ Laundry
10.0 out of 10, Exceptional, (1 review)
"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 HK$491
HK$1,313 total
includes taxes & fees
21 Jan - 22 Jan
Sleek 1BR Apt w/ Laundry
Iron/ironing board, travel cot, WiFi, bed sheets
Modern Studio Near UChicago

Apartment in Hyde Park

Modern Studio Near UChicago
9.4 out of 10, Exceptional, (12 reviews)
"Clean room and convenient location! "
United States
Gabriela
The price is HK$444
HK$1,180 total
includes taxes & fees
12 Jan - 13 Jan
Modern Studio Near UChicago
TV
Sleek & Functional 2-Bedroom Apt

Apartment in Hyde Park

Sleek & Functional 2-Bedroom Apt
9.6 out of 10, Exceptional, (4 reviews)
"Nice place for a girls trip weekend. "
United States
Madonna A.
The price is HK$452
HK$1,384 total
includes taxes & fees
12 Jan - 13 Jan
Sleek & Functional 2-Bedroom Apt
Interior
Spacious 3-bedroom apartment near downtown, FREE PARKING

Apartment in Near West Side

Spacious 3-bedroom apartment near downtown, FREE PARKING
9.4 out of 10, Exceptional, (10 reviews)
"Great place to stay that was close to downtown"
United States
Michelle B.
The price is HK$452
HK$2,587 total
includes taxes & fees
20 Jan - 21 Jan
Spacious 3-bedroom apartment near downtown, FREE PARKING
2 bedrooms, iron/ironing board, travel cot, WiFi
Explore Hyde Park: 2BR Apt on Blackstone Ave

Apartment in Hyde Park

Explore Hyde Park: 2BR Apt on Blackstone Ave
8.4 out of 10, Very good, (5 reviews)
"Host was responsive to my questions. Apartment is located in a great area of Hyde Park. "
United States
Lind A.
The price is HK$452
HK$1,384 total
includes taxes & fees
12 Jan - 13 Jan
Explore Hyde Park: 2BR Apt on Blackstone Ave
Iron/ironing board, travel cot, WiFi, bed sheets
Cozy Charm Studio Apt in Chicago

Apartment in Hyde Park

Cozy Charm Studio Apt in Chicago
10.0 out of 10, Exceptional, (2 reviews)
The price is HK$444
HK$1,180 total
includes taxes & fees
14 Jan - 15 Jan
Cozy Charm Studio Apt in Chicago
Interior
Stylish Japanese-Themed 2BR Apt Close to Downtown

Apartment in Downtown Chicago

Stylish Japanese-Themed 2BR Apt Close to Downtown
2.0 star property
The price is HK$538
HK$1,485 total
includes taxes & fees
19 Jan - 20 Jan
Stylish Japanese-Themed 2BR Apt Close to Downtown
Iron/ironing board, travel cot, WiFi, bed sheets
Studio Unit | Chic + Prime Location

Apartment in Hyde Park

Studio Unit | Chic + Prime Location
10.0 out of 10, Exceptional, (2 reviews)
"Location was just perfect!"
United States
Meg D.
The price is HK$444
HK$1,180 total
includes taxes & fees
12 Jan - 13 Jan
Studio Unit | Chic + Prime Location
TV, offices
Complete 1BR Home Sum

Apartment in Downtown Chicago

Complete 1BR Home Sum
The price is HK$491
HK$1,313 total
includes taxes & fees
12 Jan - 13 Jan
Complete 1BR Home Sum
View from property
ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments
2.0 star property
9.4 out of 10, Exceptional, (10 reviews)
"Good for family, enjoyed the stay"
United States
Karthik
The price is HK$9,761
HK$13,097 total
includes taxes & fees
16 Jan - 17 Jan
ENVITAE Hotel 4 Bedroom Luxury Apartments
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

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Great stay. Highly recommended! "
Jonathan 3-night trip
Posted 3 days ago
The Royal Sonesta Chicago Downtown

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?

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: This holiday home rental outside of Darien offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

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.