Darien Vacation Rentals

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Vacation Rentals in Darien

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (446)
"Great location and the view was fabulous! We had a very comfortable stay. Communication was excellent."
The price is ¥26,826
per night
Jul 1 - Jul 2
Sentral Michigan Avenue
Sonder Market Hall
3.5 star property
8.4 out of 10, Very Good, (99)
"The property was very clean and I loved the fact that it had a kitchen for you to cook. What I did not like was that there was no market close enough to buy groceries. I also didn't like the fact that the TV was not accesible for us, even though, I payed the late fees for a late check out. "
The price is ¥16,983
per night
Jul 8 - Jul 9
Sonder Market Hall
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (319)
"Comfortable to stay"
The price is ¥24,975
per night
Jul 2 - Jul 3
Sonder South Wabash
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, (135)
"I loved my stay at Found Chicago! The logistical communication was easy to understand and implement, and I liked that it was contactless. It was nice to use my PIN code for room entrance instead of keeping track of a key. The WiFi was sufficient for remote meetings on my laptop. And all of the amenities (lobby access, luggage locker, and printer) were convenient and easy to use. I highly recommend this hotel, and I'll plan to stay here again. "
The price is ¥17,384
per night
Jul 14 - Jul 15
Found Chicago powered by Sonder
Sonder The Burnham
3.5 star property
9.0 out of 10, Wonderful, (80)
"The stay was straight forward. Login with the passcode and get in. But no one at the reception so some nuances are not easy. For e.g. no early check in even if there are rooms. Also, for long stays, they cant change sheets or towels and no cleaning. It is an interesting concept but not so sure about long term stays like 4-5 days"
The price is ¥33,685
per night
Jul 11 - Jul 12
Sonder The Burnham
The Neighborhood Hotel-Little Italy
2.0 star property
9.8 out of 10, Exceptional, (36)
"Spacious, modern, bright, well stocked with utensils, pots and pans, towels, soaps, coffee etc. Only one elevator for many units and in case of malfunction, problematic. Overall, great concept with electronic access. The apartments/suites are beautifully appointed. "
The Neighborhood Hotel-Little Italy
WoodSpring Suites Chicago Addison
2.5 star property
6.0 out of 10, (191)
"ITS A VERY NICE AND UPBEAT ESTABLISHMENT.......I ENJOYED THE STAY ONLY THING I DIDNT LIKE WAS THERE HOUSE KEEPING SCHEDULE BUT OTHER THAN THAT ITS A NICE QUIET LOCATION WITH NICE PEOPLE"
The price is ¥14,164
per night
Jun 19 - Jun 20
WoodSpring Suites Chicago Addison
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (70)
"Enjoyed our stay at Kasa River North. Walkable distance to the riverwalk. Easy to check-in. Second time staying in Chicago Kasa and didn’t dissapoint! "
The price is ¥26,401
per night
Jun 30 - Jul 1
Kasa River North Chicago
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very Good, (111)
"We had a wonderful stay in the very comfortable apartment. I chose it for the location near Millenium Park and because it was a one bedroom. The apartment had excellent furnishings and faciilties. We had two difficulties during our stay, with the AC and with the washing machine, and both were solved quickly by the staff. They were responsive and went the extra mile to be sure everything was okay. We were also right over the L train, but with AC running I didn’t even notice it and slept great....
The price is ¥31,546
per night
Jul 7 - Jul 8
Sonder Jewelers Row
Kasa South Loop Chicago
4.0 star property
9.2 out of 10, Wonderful, (166)
"The location is unbeatable, right in the heart of downtown, making it easy to explore the city. The room was clean and cozy. The air conditioning was a little noisy though. I would recommend staying there."
Kasa South Loop Chicago
Sonder The Plymouth
3.5 star property
8.4 out of 10, Very Good, (68)
"Great place to stay and visit Chicago on foot. The property was exactly what we hoped for. "
The price is ¥22,209
per night
Jul 15 - Jul 16
Sonder The Plymouth
Luxury Home Away From Your Home
9.0 out of 10, Wonderful, (107)
"The place was nice and clean but missing some basic items such as floor mats and decent pans, otherwise our stay was good. It was near all the places we need to go"
Luxury Home Away From Your Home
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
10.0 out of 10, Exceptional, (200)
"Everything was perfect. Doormen so nice & helpful. The condo is warm & welcoming. Very easy to feel at home."
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
Sonder The Opal
3.5 star property
8.2 out of 10, Very Good, (15)
"I like that was contactless and easy to access. "
The price is ¥32,652
per night
Jul 1 - Jul 2
Sonder The Opal
Brand new entire 3 bedroom unit. 7 miles from dwntwn, 4 miles frm United Center
9.6 out of 10, Exceptional, (8)
"My friends and I stsyed with Alma for a Girl's Weekend. Our stay was comfortable and Alma was there for everything we needed. She was very accommodating. The listing was the perfect place to come to after a long day of exploring Chicago."
Brand new entire 3 bedroom unit. 7 miles from dwntwn, 4 miles frm United Center
4-Bedroom Penthouse w/ 2 Large Balconies & Rooftop
10.0 out of 10, Exceptional, (23)
"In Chicago for family wedding. Had a couple problems which were quickly addressed. Space was great, loved the balconies and rooftop. Would have liked more livingroom furniture, just one couch no chairs except barstools for a place that sleeps 8. Still, liked it enough to give 5 stars."
4-Bedroom Penthouse w/ 2 Large Balconies & Rooftop
national historic home near downtown airports no parties no events
9.0 out of 10, Wonderful, (21)
"It was an amazing property so quiet and calm area lovely host super great with communication and answering any questions I had"
The price is ¥47,313
per night
Jun 20 - Jun 21
national historic home near downtown airports no parties no events
Cozy modern unit w/ easy access to downtown Chi
9.6 out of 10, Exceptional, (18)
"It’s really confortable clean and accesible easy"
Cozy modern unit w/ easy access to downtown Chi
Sonder Greektown
3.5 star property
8.8 out of 10, Excellent, (29)
"LOCATION was terrific - central and close to all our 'outings'. Downside was NOT being able to control the thermostat. And NO response to any of our efforts to contact the property manger(s)."
The price is ¥33,753
per night
Jul 2 - Jul 3
Sonder Greektown
Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
9.8 out of 10, Exceptional, (8)
"Easy to check in, good information for parking in the area. The place was clean and nice."
The price is ¥18,266
per night
Jun 26 - Jun 27
Ground Floor Studios in Chicago by 747 Lofts
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See all available properties in Darien
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.

Other types of properties in Darien you may be interested in

Congress Plaza Hotel
3.5 star property
7.6 out of 10, Good, (7001)
"Wonderful location and a beautiful property. "
The price is ¥22,584
per night
Jul 1 - Jul 2
Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North
4.0 star property
8.0 out of 10, Very Good, (2399)
"The main lobby was inviting. Breakfast was provided. The food on the breakfast bar was only mildly warm but the omelettes were good. The staff were friendly and helpful. "
The price is ¥28,700
per night
Jul 2 - Jul 3
Embassy Suites by Hilton Chicago Downtown River North
River Hotel
4.0 star property
8.8 out of 10, Excellent, (2959)
"Great place to stay for travelers "
The price is ¥22,923
per night
Jul 2 - Jul 3
River Hotel
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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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?

National historic home near downtown airports no parties no events : This vacation home rental near Darien is located in the city center and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 5 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 5 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 Morton Arboretum. 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.

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