Darien Vacation Rentals

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Check prices for these dates

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

Our top choices for Darien vacation 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 ￥24,396
￥33,342 total
includes taxes & fees
May 10 - May 11
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 ￥43,447
￥98,931 total
includes taxes & fees
May 26 - May 27
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 ￥49,148
￥125,651 total
includes taxes & fees
May 20 - May 21
Modern West Loop Gem-City Views & Prime Location 3
1 bedroom, iron/ironing board, travel crib, 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 ￥26,648
￥49,080 total
includes taxes & fees
May 19 - May 20
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 ￥26,648
￥47,703 total
includes taxes & fees
May 4 - May 5
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
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 ￥22,819
￥44,004 total
includes taxes & fees
May 20 - May 21
Modern Comfort: 1BR Unit w/ Laundry
Design Apartment, Private Bathroom (The Oak Park Loft) | 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 ￥46,493
￥62,496 total
includes taxes & fees
May 6 - May 7
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 ￥43,470
￥66,086 total
includes taxes & fees
May 19 - May 20
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, (74 reviews)
"Nice, clean, safe house."
United States
Adrienne P.
The price is ￥18,670
￥48,958 total
includes taxes & fees
May 4 - May 5
Cozy, Comfortable and Convenient apartment. Close to everything!
1 bedroom, iron/ironing board, travel crib, 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 ￥15,230
￥33,614 total
includes taxes & fees
May 11 - May 12
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 ￥15,319
￥19,803 total
includes taxes & fees
May 4 - May 5
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 ￥30,140
￥40,131 total
includes taxes & fees
May 3 - May 4
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 ￥28,858
￥81,114 total
includes taxes & fees
May 20 - May 21
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 ￥21,542
￥50,188 total
includes taxes & fees
May 4 - May 5
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 ￥27,127
￥49,550 total
includes taxes & fees
May 11 - May 12
✽ Charming Cottage ✽ close to College/Town/Station
Iron/ironing board, travel crib, 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 ￥13,146
￥28,974 total
includes taxes & fees
May 11 - May 12
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 ￥21,066
￥45,406 total
includes taxes & fees
May 5 - May 6
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 ￥75,157
￥141,789 total
includes taxes & fees
May 1 - May 2
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.
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Top Darien Hotel Reviews

Freehand Chicago

Freehand Chicago

6/10 Okay
"Very old and dark. Bed was clean though."
Emili 1-night trip
Posted 7 hours ago
Freehand Chicago

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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  • 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!

Frequently asked questions

Can I find a vacation rental in Darien?

Yes, we give you a choice of vacation rentals close to top local attractions in Darien, or you can go with a secluded option if you want a relaxing place to 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's the top vacation rental in Darien?

ENVITAE Hotel, 4BR Luxury Modern Apartments: This vacation home rental near Darien is located in the city center and offers a barbecue grill, 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 you can cook with friends or family.

How many vacation rentals are there in Darien?

Choose from 7 Expedia vacation rentals in Darien for a memorable vacation.

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 larger area, you’ll find National Shrine of St. Therese and Burr Ridge Village Center.

What are vacation rentals like in Darien?

Vacation rentals are private accommodations you can reserve for a few days or a quick weekend in Darien. Vacation rentals feature extras such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from shared hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for a family trip.