Darien Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
15 May - 17 May
In two months
26 Jun - 28 Jun
In three months
24 Jul - 26 Jul
In four months
21 Aug - 23 Aug

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, (1,143 reviews)
"Thank you for the stay"
United States
Marco
The price is HK$1,193
HK$1,630 total
includes taxes & fees
10 May - 11 May
Sentral Michigan Avenue
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$2,124
HK$4,835 total
includes taxes & fees
26 May - 27 May
River North Rooftop With In and Out Parking 3
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, (7 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.
The price is HK$2,312
HK$6,026 total
includes taxes & fees
20 May - 21 May
Modern West Loop Gem-City Views & Prime Location 3
1 bedroom, iron/ironing board, travel cot, WiFi

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
9.8 out of 10, Exceptional, (10 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$1,293
HK$2,392 total
includes taxes & fees
19 May - 20 May
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$1,309
HK$2,343 total
includes taxes & fees
4 May - 5 May
Sunlit 1BR Apartment | Warm & Welcoming Space
Living area

Modern 3BR Apartment Near North Ave Shops

Modern 3BR Apartment Near North Ave Shops
Near North Side
The price is HK$1,050
HK$3,375 total
includes taxes & fees
30 Apr - 1 May
Modern 3BR Apartment Near North Ave Shops
TV, offices

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
8.8 out of 10, Excellent, (18 reviews)
"Great location, apt well equipped and host very responsive. Wonderful stay. "
United States
Gina G.
The price is HK$893
HK$1,788 total
includes taxes & fees
30 Apr - 1 May
Modern Comfort: 1BR Unit w/ Laundry
Exterior

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The Oak Park Loft
Living area

LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"It was very clean and as described/ pictured. The location was absolutely perfect being within a short walk to millennium park, restaurants and stores. The batteries were low in the remote and the host reached out to us around the same time. We received batteries within 10 minutes of letting them know."
United States
Amber W.
The price is HK$3,872
HK$5,155 total
includes taxes & fees
2 May - 3 May
LIVN Millennium Park Downtown Chicago 2BR
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (191 reviews)
"Having a kitchen is great."
United States
Mark
The price is HK$1,236
HK$2,187 total
includes taxes & fees
30 Apr - 1 May
Kasa River North Chicago
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)
"Nice, clean, safe house."
United States
Adrienne P.
The price is HK$917
HK$2,404 total
includes taxes & fees
4 May - 5 May
Cozy, Comfortable and Convenient apartment. Close to everything!
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$776
HK$1,670 total
includes taxes & fees
26 May - 27 May
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, (12 reviews)
"Had a great experience here, and also close to the airport!"
United States
Yafeat D.
The price is HK$744
HK$964 total
includes taxes & fees
30 Apr - 1 May
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
Living area

LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Everything went well"
United States
Ryan W.
The price is HK$1,199
HK$1,601 total
includes taxes & fees
30 Apr - 1 May
LIVN West Loop Chicago 2 BR City View
Exterior

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (16 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
The price is HK$1,458
HK$4,033 total
includes taxes & fees
20 May - 21 May
Spacious 4BR Central Apartment w/ Skyline Views
Dining

LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.8 out of 10, Excellent, (45 reviews)
"Nice overall"
United States
Hell
The price is HK$1,058
HK$2,465 total
includes taxes & fees
30 Apr - 1 May
LUXE 3 BR, 2 BA + Hot Tub
Outdoor dining

✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (64 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$1,332
HK$2,425 total
includes taxes & fees
28 May - 29 May
✽ Charming Cottage ✽ close to College/Town/Station
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$643
HK$1,416 total
includes taxes & fees
11 May - 12 May
Modern Studio Unit Near UChicago
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, (99 reviews)
"Everything was good!"
United States
Brio
The price is HK$1,030
HK$2,220 total
includes taxes & fees
5 May - 6 May
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
TV, offices

Downtown Chicago Stay with Free In & Out Parking 4

Downtown Chicago Stay with Free In & Out Parking 4
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"Our stay was wonderful. The views were fantastic. The apartment was centrally located so we were able to walk to restaurants, museums, and theaters. We bookmarked this location for future stays."
United States
Renae S.
The price is HK$4,263
HK$7,815 total
includes taxes & fees
17 May - 18 May
Downtown Chicago Stay with Free In & Out Parking 4
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Darien Hotel Reviews

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

8/10 Good
"Property and room were clean. The clothing drawers were big enough for all of our stuff! Closet also had a lot of hangers! Bathroom needed a little upgrade but not bad. Breakfast was fantastic! Hotel was in a great location as well. Would definitely stay there again. We didn’t use valet but used the self parking garage a block away. Should have used Spot Hero to save more money but it was still $75 cheaper to park there instead of valet."
julie 2-night trip
Posted 4 hours ago
Embassy Suites by Hilton Chicago Downtown River North

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!

Explore a world of travel with Expedia

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?

ENVITAE Hotel, 4BR Luxury Modern Apartments: This holiday home rental outside of Darien is located in the city centre, and offers a BBQ, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 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 The Forge: Lemont Quarries Adventure 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.