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Compare 464 Vacation Homes in Darien with updated reviews, rates, and availability.

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Your Next Vacation Home

9.8 out of 10, Exceptional, (30)
"Very clean, extremely nice home. "
The price is SAR 563
SAR 1,080 total
includes taxes & fees
29 Jan - 30 Jan
Your Next Vacation Home

Gorgeous historic mansion on UChicago campus. Renovation with original detail.

10.0 out of 10, Exceptional, (3)
"I wish we came across this property 4 years ago when we dropped off our daughter at the UofC campus. Location is amazing, 7 minutes walk to the campus. The house is spacious and accommodates a large group of people. Very clean and what was really appreciated it was so well stocked - nice shampoos and lotions in all bathrooms, paper towels in the kitchen, a welcome bottle of bubbly wine from the hosts. The check-in and out process was also incredibly easy, and the hosts were very welcoming and...
Gorgeous historic mansion on UChicago campus. Renovation with original detail.

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

Cheerful 4 bedroom smart home w/ indoor fireplace

7.8 out of 10, Good, (12)
"Loved the place and host was super helpful when needed! "
Cheerful 4 bedroom smart home w/ indoor fireplace

3BD/2BA DUAL LEVEL WITH FAMILY ROOM KING BED/LAUNDRY ROOM- IDEAL 4 EXTENDED STAY

10.0 out of 10, Exceptional, (73)
"This property is in a great location that is quiet and convenient. The property was extremely clean and had essentials for our stay. This property was a great option for our family to stay together and there was plenty of room for all 6 of us adults. Fantastic place. Most definitely would stay again!!!"
3BD/2BA DUAL LEVEL WITH FAMILY ROOM KING BED/LAUNDRY ROOM- IDEAL 4 EXTENDED STAY

Spacious open concept home w/ game room + firepit

9.8 out of 10, Exceptional, (52)
"This property was in a great location! Easy to find and central to make getting to the surrounding cities super easy. The property was easy to access, which was my number one worry, and we had a fantastic time with our stay. Thank you, Amanda!"
Spacious open concept home w/ game room + firepit

Cheery 2+bedroom home with free parking on premises

9.8 out of 10, Exceptional, (33)
"Third time staying at this property. Great property and location. "
Cheery 2+bedroom home with free parking on premises

Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover

9.8 out of 10, Exceptional, (6)
"Great location so convenient to everything! Great to have a garage to park. Also, great to have the 2 bedrooms with their own bathrooms! Property met our needs. It was not dirty but was not as clean as it could have been. (Mainly the floors) Overall the house worked great for us! "
Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover

Berwyn Beauty

10.0 out of 10, Exceptional, (12)
"Perfect for visiting family by with more space than an hotel. A nice neighborhood. Away from the hustle and bustle of downtown but an easy drive for vacationers. "
Berwyn Beauty

Spacious and family friendly getaway. 8 mins from Chicago Premium Outlet Mall.

10.0 out of 10, Exceptional, (16)
"In a quiet part of town, very spacious and clean"
The price is SAR 1,872
SAR 3,582 total
includes taxes & fees
23 Feb - 24 Feb
Spacious and family friendly getaway. 8 mins from Chicago Premium Outlet Mall.

LuxHome up to 8 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins

9.4 out of 10, Exceptional, (3)
"Good stay. "
LuxHome up to 8 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins

Stunning 4-bedroom 4-bath building in Wicker Park! + Parking

Stunning 4-bedroom 4-bath building in Wicker Park! + Parking

Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!

Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!

LUXE 3 BR, 2 BA + Hot Tub

9.0 out of 10, Wonderful, (20)
"Everything was nice and cleaned.Will stay again "
The price is SAR 563
SAR 1,175 total
includes taxes & fees
26 Jan - 27 Jan
LUXE 3 BR, 2 BA + Hot Tub

The Comfy King Ranch - King Bed/Spacious Home/Fast WiFi/Free Parking

9.6 out of 10, Exceptional, (45)
"We had a short stay in this property and we wished it could have been longer. The house was very nice, clean and the communication was great!! It is a short drive to the airport and to downtown. We would definitely stay here again"
The price is SAR 608
SAR 1,334 total
includes taxes & fees
23 Feb - 24 Feb
The Comfy King Ranch - King Bed/Spacious Home/Fast WiFi/Free Parking

Stunning / Spacious 6BD Home + garage - Bucktown!

9.2 out of 10, Wonderful, (30)
"Location is great, size of the house is great with queen beds in all room and even one with a King bed. Basement was very cold, ( it’s winter) so that bedroom was not used but wasn’t needed anyways. The house needs a really good cleaning especially the kitchen especially the cabinets. Also coffee maker is tiny, doesn’t make sense considering the size of the house. Ironing board had no cover just metal frame, kitchen was not stocked properly for the size of the house. Loved the fact there was...
Stunning / Spacious 6BD Home + garage - Bucktown!

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

10.0 out of 10, Exceptional, (163)
"Great location, lots of space for gathering and hanging out. Tons of sleeping areas, air mattresses couches, futons, etc. Great for large groups of adults. Caution: Lots of stairs."
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square

10.0 out of 10, Exceptional, (33)
"We had a terrific stay at here. The apartment was sparkly clean. The linens were like new. The bed was comfortable and cozy. It’s a basement apartment but you don’t feel “underground” at all. It’s light and airy, laid out well with plenty of living space. It’s on a quiet residential block and conveniently located for public transportation and walking to restaurants. Caitlin checked in with us just the right amount—to be sure the temperature was right (it was) and if we needed anything (we...
Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square

Furnished Private home in Aurora sleeps 9 guests

9.4 out of 10, Exceptional, (73)
"Our party came to town to visit relatives during Christmas holidays. The house was in good working order and met our needs. Beds were comfortable with easy check- in/ check- out."
Furnished Private home in Aurora sleeps 9 guests
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 property types in Darien

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (661)
"We stayed at Sentral after a trip to the Shedd with the kids. We had a great day and evening in the city and when we finally got to our room, we couldn't believe it! It was so spacious, we could have stayed for a week. Full kitchen, stocked with appliances, utensils, plates and glasses. Two full baths, two bedrooms and more closet space than we could have possibly used. Location was close to everything you'd need. We'll definitely be back."
The price is SAR 411
SAR 593 total
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 SAR 412
SAR 484 total
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 SAR 230
SAR 269 total
includes taxes & fees
17 Feb - 18 Feb
Sonder Market Hall
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.