Darien Holiday Rentals

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Holiday Rentals in Darien

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (729)
"Large sunny rooms with excellent amenities and views. "
The price is NZ$265
includes taxes & fees
20 Apr - 21 Apr
Sentral Michigan Avenue

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (473)
"Good place"
The price is NZ$230
includes taxes & fees
20 Apr - 21 Apr
Sonder South Wabash

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (271)
"Very clean l, quiet and well thought out. Had everything we needed and the bed was super comfortable! Great having a 12 cup coffee pot! Parking was close and although not a lot of close options to restaurants or shopping, there were many more options within a 15-20 min walk. Would definitely stay here again!"
The price is NZ$228
includes taxes & fees
21 Apr - 22 Apr
Sonder Market Hall

Sonder The Burnham Apartments

3.5 star property
8.8 out of 10, Excellent, (159)
"We loved the proximity to Union Station as well as Willis Tower and St. Patrick's Church. Casual dining options were very close and convenient. The apt was very clean. The view was of an alley which as expected had trash around dumpsters. It was brightly lit at night. A number of panhandlers in the area, which wasn't a complete surprise considering it's a city. The loveseat was the worst part... extremely uncomfortable and worn out. That being said, we would stay there again, because the check...
The price is NZ$242
includes taxes & fees
21 Apr - 22 Apr
Sonder The Burnham Apartments

Sonder Jewelers Row

3.5 star property
8.4 out of 10, Very good, (146)
"This was the perfect stay for us this past weekend "
The price is NZ$307
includes taxes & fees
20 Apr - 21 Apr
Sonder Jewelers Row

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (275)
"We had a great time"
Kasa South Loop Chicago

The Neighborhood Hotel-Little Italy

3.5 star property
9.8 out of 10, Exceptional, (147)
"Very clean property, very convenient area offering restaurants, bars, groceries within walkin distance. Staff/owners very helpful. Answered all our questions promptly. Overall very pleased with our stay and I highly recommend this hotel when visiting Chicago."
The Neighborhood Hotel-Little Italy

Sonder The Plymouth

3.5 star property
8.4 out of 10, Very good, (97)
"The apartment was perfect. Location made everything walkable. Super clean. Bright rooms. Bed was super comfy. I can’t say enough good things about this place. I loved it and would stay here again on my next trip to Chicago "
The price is NZ$279
includes taxes & fees
12 May - 13 May
Sonder The Plymouth

Sonder The Opal

3.5 star property
8.6 out of 10, Excellent, (33)
"Very very cozy and clean! All messages and questions were answered promptly, and checking in and out was smooth! getting into the building was easy, everything was perfect. "
The price is NZ$191
includes taxes & fees
11 May - 12 May
Sonder The Opal

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (136)
"Wow was the word we all exclaimed when we walked in the door. Beautiful corner rooms, light and airy, wonderful experience. "
The price is NZ$258
includes taxes & fees
20 Apr - 21 Apr
Kasa River North Chicago

Sonder Greektown

3.5 star property
9.0 out of 10, Wonderful, (47)
"I was in the mood to walk, so I put on my sneakers and did just that. The property is a little off the beaten track, and I was not that impressed with Greek Town, but I would stay again because the property itself was quite nice. "
The price is NZ$283
includes taxes & fees
20 Apr - 21 Apr
Sonder Greektown

HUGE! 3bdrm Private HOME-Garage-RoofDeck Skyline view-EVTesla-PETS OK-Sleeps12

10.0 out of 10, Exceptional, (3)
"We were happy with the house- it’s as described and the location was great. Loved having the garage, not having to worry about finding parking "
HUGE! 3bdrm Private HOME-Garage-RoofDeck Skyline view-EVTesla-PETS OK-Sleeps12

Luxury Home Away From Your Home

9.0 out of 10, Wonderful, (117)
"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

Classic Lincoln Park 2 bedroom condo- parking included

9.8 out of 10, Exceptional, (65)
"Amazing stay! Great communication and wonderful property conveniently located close to someGood eats (Lincoln park Corner Kitchen, Pequod’s, Sweet Mandy B’s and Floriole Cafe). Our family had a great time. Thank you Stacy!"
Classic Lincoln Park 2 bedroom condo- parking included

NEW LUXURY CONDO WITH PATIO DECK

10.0 out of 10, Exceptional, (158)
"It was an amazing weekend with family and friends. The space was perfect for the occasion. Enough space for everyone to be comfortable. The open concept was everything!! I’ll definitely rent again!"
NEW LUXURY CONDO WITH PATIO DECK

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."
The price is NZ$525
includes taxes & fees
18 May - 19 May
Ground Floor Studios in Chicago by 747 Lofts

Remodeled West Loop Apartment Near United Center

9.2 out of 10, Wonderful, (34)
"Everything was nice and neat. They were super easy to communicate with. We had a little issue with the main building door keyless entry. Other than that everything was great."
Remodeled West Loop Apartment Near United Center

Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!

7.8 out of 10, Good, (7)
"I would stay again and the communication was on point. Thank you for having us."
Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!

Cozy Charming •Art 🎨 • Food🌮 Close to Train 🚉 • Parking!

9.8 out of 10, Exceptional, (83)
"7 minute walk from Metra, about 15 minutes from downtown Chicago. There is NO hot tub, though. It's listed in the amenities but I asked and the owner was honest in telling me there wasn't one. Great communica"
Cozy Charming •Art 🎨 • Food🌮 Close to Train 🚉 • Parking!

LUXE 3 BR, 2 BA + Hot Tub

9.2 out of 10, Wonderful, (23)
"This property was is in a good neighborhood nice and clean I really enjoy myself Thanks"
The price is NZ$668
includes taxes & fees
20 Apr - 21 Apr
LUXE 3 BR, 2 BA + Hot Tub
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

Embassy Suites by Hilton Chicago Downtown River North

4.0 star property
8.4 out of 10, Very good, (3905)
"Very convenient place"
The price is NZ$296
includes taxes & fees
21 Apr - 22 Apr
Embassy Suites by Hilton Chicago Downtown River North

Crowne Plaza Chicago West Loop by IHG

3.5 star property
8.8 out of 10, Excellent, (1020)
"very clean "
The price is NZ$244
includes taxes & fees
20 Apr - 21 Apr
Crowne Plaza Chicago West Loop by IHG

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very good, (8695)
"The hotel was perfect, very convenient considering we went to the hwassa concert right across the street at the auditorium. Will definitely be staying here again."
The price is NZ$198
includes taxes & fees
21 Apr - 22 Apr
Congress Plaza 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.

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?

Cozy Home Sweet Homewood. : This holiday home rental outside of Darien is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in Darien?

Choose from 8 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.