Search Vacation Homes in Darien

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation
Cozy Midway Home
2.0 star property
9.8 out of 10, Exceptional, (10)
"Place was nice, neighborhood was nice, and it was close to the airport. "
Cozy Midway Home
Great 3 bedroom rental unit near Logan Square
9.4 out of 10, Exceptional, (20)
"David was a great host and responded super fast to our questions! The property is gorgeous and is super close to the blue line. The neighborhood is beautiful and had everything we needed within a 3-10 minute walk!"
Great 3 bedroom rental unit near Logan Square
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Elegant Mayor's Manor in Central Chicago - 9 Beds + Futons, Close to Downtown!
9.8 out of 10, Exceptional, (12)
"Before and throughout the trip the hosts were very responsive and helpful. We fully booked the house and there was plenty of room for us in the common areas and backyard. The neighborhood around also has an excellent coffee shop, bar, and food areas within walking distance. Next time I bring a group to the Bridgeport area I’ll definitely try to book this property again "
Elegant Mayor's Manor in Central Chicago - 9 Beds + Futons, Close to Downtown!
Amazing 4BR/4BA Oasis w/ Rooftop & Stunning Design
10.0 out of 10, Exceptional, (2)
"As good as advertised. Plenty of room for our group. Definitely recommend. "
Amazing 4BR/4BA Oasis w/ Rooftop & Stunning Design
Charming 3-bedroom house with AC and WiFi in serene Des Plaines near O’Hare
2.0 star property
6.8 out of 10, (3)
"Quick stat to check on an aging family member."
The price is HK$1,632
HK$2,528 total
includes taxes & fees
12 Nov - 13 Nov
Charming 3-bedroom house with AC and WiFi in serene Des Plaines near O’Hare
Furnished Private home in Aurora sleeps 9 guests
9.4 out of 10, Exceptional, (69)
"We had a nice stay along with our 2 dogs. The home had everything we needed. Highly recommend! Dori was an excellent host! "
Furnished Private home in Aurora sleeps 9 guests
Wicker Park Entire House, Private Yard and Parking!
10.0 out of 10, Exceptional, (6)
"We loved this place. It was perfect for our work trip to Chicago. The neighborhood is awesome and the host was very organized and super easy to communicate with. Highly recommend this house!"
Wicker Park Entire House, Private Yard and Parking!
Spacious 5 BR / King Size Beds + Private Parking!
9.6 out of 10, Exceptional, (8)
"My coworkers and I came to Chicago for a conference and this was the perfect place to stay for it. The rooms were well separated so noise didn't travel between them, and the house was clean and comfortable. The host was extremely accommodating, and it was only a short distance from downtown Chicago."
Spacious 5 BR / King Size Beds + Private Parking!
Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover
9.2 out of 10, Wonderful, (7)
"The house was good, plenty of space. The steps were hard to get up and down but the upstairs was a nice space. House had a bit of a musty odor and the windows could use a cleaning. One night while watching a movie, we received a text stating we were had a loud party and to keep it down. They must have big brother watching us as the only party going on that night was in the movie. Overall the house was close to the city but in a nice Neiborhood. Having a fenced yard with off street parking...
Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover
Pet-Friendly Bartlett Farmhouse w/ Deck!
9.6 out of 10, Exceptional, (5)
"My mother and aunt LOVED the decor."
Pet-Friendly Bartlett Farmhouse w/ Deck!
Cozy Home Sweet Homewood.
10.0 out of 10, Exceptional, (13)
"My mom and I live in Huntsville Alabama and came to visit family and friends in the area and the Homewood house was the perfect location to stay. I miss home so much. It was very comfortable and cute. I will definitely make reservations for next year. Forget staying in a hotel. 😉😅"
Cozy Home Sweet Homewood.
King Bed, DIsney+, Spacious, Family-Friendly House
10.0 out of 10, Exceptional, (18)
"My daughter goes to school in Chicago and needed surgery but we live in Holland, MI. This house was perfect for us to all stay together during this time and we could take care of her as a family. We got to bring the dog which helped ease anxieties and stress! The neighbor was lovely and I enjoyed my breaks from nursing by walking the dog. Thank you so much!!!! 😊 "
The price is HK$1,422
HK$2,856 total
includes taxes & fees
18 Nov - 19 Nov
King Bed, DIsney+, Spacious, Family-Friendly House
Chicago-burb -Medinah -1 King and 1 Queen beds
9.4 out of 10, Exceptional, (14)
"Everything was exactly as it was described. Super clean, easy to find, great neighborhood. "
Chicago-burb -Medinah -1 King and 1 Queen beds
5 minutes from Midway Int'l Airport Single Family Home.
9.2 out of 10, Wonderful, (5)
"Everything was fine. Owner was easy to work with and the property met our needs."
5 minutes from Midway Int'l Airport Single Family Home.
4 Mi to Dtwn Chicago: Modern Home w/ Outdoor Space
2.0 star property
4.0 out of 10, (1)
"This place looks nice in photos but is not ready for renting. It does not have a stocked kitchen or other basic amenities. Owner had to send glasses, silverware, hangers, iron, ironing board via Target on the second day of our stay. The dishwasher doesn’t work. Many of the drawers are broken. The deadbolt front door doesn’t lock from outside. "
4 Mi to Dtwn Chicago: Modern Home w/ Outdoor Space
Willowbrook Gem 3-bedroom house with AC, WiFi, next to Forest Preserve
2.0 star property
9.8 out of 10, Exceptional, (6)
"Perfect location outside of Chicago. We were visiting friends in nearby Hinsdale. Place is better than the photos. Easy check in process, great communication with host. Place is perfect, spotless and clean, seems brand new. Comfy beds. Keurig coffee was great. Would stay again. Highly recommend! ! "
Willowbrook Gem 3-bedroom house with AC, WiFi, next to Forest Preserve
Spacious Deck & Balcony, Game Area, Garage
10.0 out of 10, Exceptional, (2)
"This is a large property--having not just 5 bedrooms, but lots of living space. We had plenty of room for a large group to stay and spread out. It had everything we needed."
The price is HK$1,143
HK$3,513 total
includes taxes & fees
6 Nov - 7 Nov
Spacious Deck & Balcony, Game Area, Garage
Clarendon Hills Top Floor
6.6 out of 10, (4)
"The house was nice, in a quiet area. The bedrooms were great. It was a little nerve wracking when the lower unit was rented, as we didn't want to disturb them. "
Clarendon Hills Top Floor
Charming 3-bedroom house in fantastic Plainfield, 10 min to Naperville
2.0 star property
10.0 out of 10, Exceptional, (2)
"Wow! I cant stress enough how amazing this place is. Tucked away on a cul de sac street and very quiet. The nice quaint aesthetic is so charming. Once stepping inside my family and I were blown away by how clean, spacious and well decorated it was. It was so cozy and comfortable. The kitchen offered everything you may need. We were able to enjoy the spacious backyard and enclosed patio space. The overall location was great since i have family in plainfield and joliet. We absolutely enjoyed our...
Charming 3-bedroom house in fantastic Plainfield, 10 min to Naperville
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.
Don't see what you're looking for?
See all available properties in Darien
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Darien

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (580)
"Everything was great!"
The price is HK$972
HK$1,369 total
includes taxes & fees
24 Nov - 25 Nov
Sentral Michigan Avenue
Sonder Market Hall
3.5 star property
8.6 out of 10, Excellent, (197)
"Amazing and cant wait to stay here again!!"
The price is HK$563
HK$661 total
includes taxes & fees
3 Dec - 4 Dec
Sonder Market Hall
Sonder South Wabash
3.5 star property
9.0 out of 10, Wonderful, (387)
"Clean and well located. We had access to the green and red line trains a few stops away from the loop. Entering the building was easy and convenient. Apartment was clean and spacious!! "
The price is HK$1,099
HK$1,290 total
includes taxes & fees
25 Nov - 26 Nov
Sonder South Wabash
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.