Darien Holiday Rentals

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Check prices for these dates

In two weeks
27 Mar - 29 Mar
In two months
8 May - 10 May
In three months
5 Jun - 7 Jun
In four months
3 Jul - 5 Jul

Our top choices for Darien holiday rentals

Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,104 reviews)
"Best full kitchen multi-room family lodging"
United States
Lee
The price is HK$925
HK$1,315 total
includes taxes & fees
19 Mar - 20 Mar
Sentral Michigan Avenue
TV, offices

Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment
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$1,834 total
includes taxes & fees
17 Mar - 18 Mar
Sun-Drenched 1BR Apartment
TV, offices

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
9.2 out of 10, Wonderful, (15 reviews)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is HK$884
HK$1,825 total
includes taxes & fees
12 Mar - 13 Mar
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, (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$1,526
HK$3,529 total
includes taxes & fees
18 Mar - 19 Mar
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, (8 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$884
HK$1,825 total
includes taxes & fees
15 Mar - 16 Mar
West Loop Living – Bright 1BR
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (186 reviews)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Exterior

A quiet stay while you are away

A quiet stay while you are away
Oak Park
9.8 out of 10, Exceptional, (34 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$1,884 total
includes taxes & fees
18 Mar - 19 Mar
A quiet stay while you are away
Terrace/patio

- Fully-Equipped Condo - King Bed - Massive yard -

- Fully-Equipped Condo - King Bed - Massive yard -
Geneva
10.0 out of 10, Exceptional, (38 reviews)
"We really enjoyed our stay here. The kitchen had everything we needed and the house was very nice. Finding the driveway was a bit tricky in the dark. Thank you for a welcoming place to call home while we were in town for a wedding. "
United States
Cathy
The price is HK$697
HK$1,949 total
includes taxes & fees
12 Mar - 13 Mar
- Fully-Equipped Condo - King Bed - Massive yard -
Fridge, microwave, oven, stovetop

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Westchester
9.8 out of 10, Exceptional, (20 reviews)
"Great place Great location "
United States
Josh W.
The price is HK$1,125
HK$2,970 total
includes taxes & fees
12 Mar - 13 Mar
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
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, (57 reviews)
"Home was exactly what we were needing fir our stay. Host was responsive and timely. "
United States
Stephanie H.
The price is HK$1,213
HK$2,590 total
includes taxes & fees
15 Mar - 16 Mar
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Outdoor dining

✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (59 reviews)
"This is a cozy little home close to all the things we love about visiting Wheaton. "
United States
Nancy F.
The price is HK$1,330
HK$2,413 total
includes taxes & fees
12 Mar - 13 Mar
✽ Charming Cottage ✽ close to College/Town/Station
Interior

Cabin 105 by 747 Lofts

Cabin 105 by 747 Lofts
2.0 star property
West Town
10.0 out of 10, Exceptional, (1 review)
The price is HK$527
HK$1,589 total
includes taxes & fees
15 Mar - 16 Mar
Cabin 105 by 747 Lofts
Interior

Oak Park Queen

Oak Park Queen
Oak Park
8.2 out of 10, Very good, (33 reviews)
"The property was very clean and comfortable. Good location. The owner was responsive."
United States
Susan S.
The price is HK$697
HK$1,756 total
includes taxes & fees
12 Mar - 13 Mar
Oak Park Queen
1 bedroom, WiFi, bed sheets

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 review)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is HK$884
HK$1,834 total
includes taxes & fees
17 Mar - 18 Mar
1BR Modern Luxe Apt with In-Unit Laundry
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$845
HK$1,935 total
includes taxes & fees
16 Mar - 17 Mar
Your Perfect 2BR Home
Interior

Stylish Luxe King bed w/Free Parkng near DT Oak Pk

Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Oak Park
9.6 out of 10, Exceptional, (98 reviews)
"Cozy place, host was very helpful and responded quickly to all my concerns. I would definitely stay there again. "
United States
Deborah R.
The price is HK$831
HK$1,936 total
includes taxes & fees
23 Mar - 24 Mar
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Exterior

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (10 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
Spacious 4BR Central Apartment w/ Skyline Views
Smart TV

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Maywood
8.0 out of 10, Very good, (21 reviews)
"Easy to access, big place, great for a group that needs to have several rooms and beds. Would definitely stay again"
United States
JOSE S.
The price is HK$1,162
HK$2,373 total
includes taxes & fees
23 Mar - 24 Mar
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
1 bedroom, iron/ironing board, travel cot, WiFi

Charming Sunlit 1BR Apartment

Charming Sunlit 1BR Apartment
Irving Park
9.2 out of 10, Wonderful, (12 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$540
HK$1,373 total
includes taxes & fees
15 Mar - 16 Mar
Charming Sunlit 1BR Apartment
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, (4 reviews)
"Had a great experience here, and also close to the airport!"
United States
Yafeat D.
The price is HK$743
HK$962 total
includes taxes & fees
22 Mar - 23 Mar
Cozy Garden Suite minutes from O'hare and Rosemont + 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

L7 Chicago by LOTTE

L7 Chicago by LOTTE

10/10 Excellent
"Excellent king room, no view unfortunately but it was so comfortable and quiet. Hotel is right in the heart of things. It has a bar and restaurant downstairs and a 7-11 shop on the corner. It's close to several L stations too but walkable to many places too."
Marion 4-night trip
Posted 3 hours ago
L7 Chicago by LOTTE

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
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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?

Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!: This holiday home rental outside of Darien is on a lake, and equipped with air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 5 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.