Darien Holiday Rentals

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Holiday Rentals in Darien

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (661)
"I loved the apartment like hotel rooms. The decor and special touches were really nice! Location and pricing was also great!I just wish they had more elevators, with so many floors elevator waits were a little long. The staff was great as well and answered everything throughly that I needed. Will definitely be back "
The price is NZ$279
includes taxes & fees
27 Jan - 28 Jan
Sentral Michigan Avenue

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (419)
"Great place to spend a few days. "
The price is NZ$228
includes taxes & fees
28 Jan - 29 Jan
Sonder South Wabash

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (244)
"New. Modern. Cozy.Clean & quiet place. Will book it again!"
The price is NZ$125
includes taxes & fees
17 Feb - 18 Feb
Sonder Market Hall

Sonder The Burnham Apartments

3.5 star property
8.8 out of 10, Excellent, (132)
"If you are a walker and just want to explore what Chicago has to offer please book this place. You can store your bags before and after checkin/out and the lobby is so nice and quiet. "
The price is NZ$260
includes taxes & fees
9 Feb - 10 Feb
Sonder The Burnham Apartments

Found Chicago powered by Sonder

3.5 star property
7.6 out of 10, Good, (183)
"It was a Great option, straight and contactless."
The price is NZ$250
includes taxes & fees
18 Feb - 19 Feb
Found Chicago powered by Sonder

The Neighborhood Hotel-Little Italy

3.5 star property
9.6 out of 10, Exceptional, (123)
"This property was so clean and safe with so many options to eat parking was easy with the parking app. I cannot wait to stay here again. I was at peace. No one was loud or obnoxious. It was perfect if you’re second-guessing this property don’t it’s so convenient and very easy to check in and out of Little Italy was the best. Thank you for such a great experience. Oh, and the heater above the door as you walk in is amazing as well. Lol"
The Neighborhood Hotel-Little Italy

Sonder Jewelers Row

3.5 star property
8.2 out of 10, Very good, (136)
"Sonder check in experience as a first timer was super easy! Great instructions and no issues entering or exiting the property. Property was in great condition with all the amenities you could need. Only downside was the cigar bar downstairs... you could at certain times of day smell the cigar scent in our room upstairs. Not a huge issue, but if you were sensitive to the smell it would not be ideal."
The price is NZ$212
includes taxes & fees
18 Feb - 19 Feb
Sonder Jewelers Row

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (251)
"Everything was great from the beginning. From the instructions on where to park and enter to how to exit. "
Kasa South Loop Chicago

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (118)
"It was nice, comfortable and close to everything downtown."
The price is NZ$174
includes taxes & fees
29 Jan - 30 Jan
Kasa River North Chicago

Sonder The Plymouth

3.5 star property
8.4 out of 10, Very good, (88)
"Loved the location. "
The price is NZ$214
includes taxes & fees
23 Feb - 24 Feb
Sonder The Plymouth

Sonder The Opal

3.5 star property
8.6 out of 10, Excellent, (28)
"We loved the location in River North with shops around plenty of nice restaurants. Walkable and good buses around. Apartment was very nice, we were 5 adults. A bit noisy because of bar nearby ( it depends of your tolerance to noise. Some of us were disturbed some heard nothing). We enjoyed our stay !"
The price is NZ$257
includes taxes & fees
19 Feb - 20 Feb
Sonder The Opal

Luxury Home Away From Your Home

9.0 out of 10, Wonderful, (116)
"Had a great time at Ms. Linnie’s place! She was incredibly responsive and helpful. The house was clean and comfortable, and I loved that there were 2 full bathrooms! I was a little nervous about the neighborhood as we were definitely looked at as outsiders, but no one bothered us and we walked to Maxwell Street Polish and back just fine (which is fantastic, btw). I did love the gated yard in back with two parking spots, so we had our own space. Would definitely stay again!"
Luxury Home Away From Your Home

Sonder Greektown

3.5 star property
9.0 out of 10, Wonderful, (36)
"The place was awesome, they had to kick out the people before me, so getting my room was a little bit late "
The price is NZ$372
includes taxes & fees
3 Feb - 4 Feb
Sonder Greektown

51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi

10.0 out of 10, Exceptional, (217)
"Thank you so much for sharing your penthouse! We had a very relaxing time and hope to come back sometime when it is a little warmer and we can explore the area more! It was an amazing location for sure! There were so many nice touches from the ample number of outlets/places to charge, the plentiful kleenex boxes, the kitchen amenities and even a fan. We felt right at home and literally needed nothing. Thank you so much for making this past week exactly what we needed!"
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi

Experience Chicago living near United Center

9.4 out of 10, Exceptional, (13)
"Everything was as advertised. Neighbors with dogs barking in the night and car honking/other outside elements can be disruptive if you're a light sleeper. Very quick and fast communication with host even at 2am. Would recommend."
Experience Chicago living near United Center

Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC

10.0 out of 10, Exceptional, (271)
"Loved this hip 3 bedroom! Lots of art prints and tasteful decor. Well stocked kitchen and comfy beds. Neighborhood had many restaurant offerings."
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.6 out of 10, Exceptional, (12)
"Overall for solo travel is recommended."
Ground Floor Studios in Chicago by 747 Lofts

1F Chicago's Little italy Graystone nearDowntown

10.0 out of 10, Exceptional, (123)
"Nice 3 bedroom, 2 bath in a quiet neighborhood The three of us loved this clean and cozy apartment. "
1F Chicago's Little italy Graystone nearDowntown

Elevate Your Experience: PH#1, A Penthouse Above the Rest in Chicago

10.0 out of 10, Exceptional, (284)
"We stayed 5 days beginning Christmas Day and it was one of the most memorable vacations we’ve taken as a family. Our hosts were perfect in that they were always quick to respond (1-2 minutes), but everything was so well planned that we never really needed anything. The patio balcony is HUGE and you can see everything from 55 stories. Great views of the lake. Easy access to all of downtown via Uber or a short walk. We can’t say enough about this apartment, and we’d love to stay there again. ...
Elevate Your Experience: PH#1, A Penthouse Above the Rest in Chicago

Roscoe Village Inn -Guesthouse - Walk to Chicago's Wrigley Field

10.0 out of 10, Exceptional, (167)
"Fantastic location and an outstanding host! I had an amazing stay. The space was ideal for my needs, offering a comfortable and convenient setting to assist my daughter with her wedding preparations. It had everything I was looking for—well-equipped with great amenities and in a prime location. The property was spotless, peaceful, and provided everything needed for a smooth and enjoyable experience. Easy street parking was always available! I highly recommend this place to anyone looking for a...
Roscoe Village Inn -Guesthouse - Walk to Chicago's Wrigley Field
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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Other types of properties in Darien you may be interested in

Congress Plaza Hotel

3.5 star property
7.8 out of 10, Good, (8426)
"We stayed here about a year ago and were placed in the Buckingham palace portion. We were not impressed at all and I wrote a review about it. This stay was far different this time! We got a lakeview room and were placed in the south tower. The room was very big and spacious. We had normal pillows this time and the heater actually worked thankfully. The view was amazing. The only problems were that our shower door leaked no matter what we did to try to stop it, and the hallways were dirty. We...
The price is NZ$193
includes taxes & fees
24 Jan - 25 Jan
Congress Plaza Hotel

River Hotel

4.0 star property
8.8 out of 10, Excellent, (3724)
"Enjoyed our stay. The hotel is a no frills hotel but the location is hard to beat right on the river. Our room had a fantastic view and was clean. We stayed two nights and both days housekeeping came around and refreshed towels and cleaned up. Overall we would come back to the River Hotel."
The price is NZ$176
includes taxes & fees
23 Feb - 24 Feb
River Hotel

Pendry Chicago

4.5 star property
9.4 out of 10, Exceptional, (1001)
"We only stayed one night after a party. Great place! We loved it! Valet service made it easy to get in and out. Staff in the Boozy Team room was excellent."
The price is NZ$415
includes taxes & fees
5 Feb - 6 Feb
Pendry Chicago
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.

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?

Luxury Home Away From Your Home: This holiday home rental outside of Darien is equipped with a BBQ, air conditioning and free WiFi to help you feel comfortable during your stay. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

How many holiday rentals are there in Darien?

Choose from 6 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 PGN Jump N' Fun Entertainment, 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.