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Top Holiday Rentals in Darien

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (846)
"We would stay here again. Very happy with our stay "
The price is £171
includes taxes & fees
4 Aug - 5 Aug
Sentral Michigan Avenue

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.2 out of 10, Very good, (335)
"The property canceled on us 4 hours prior to check in"
The price is £111
includes taxes & fees
17 Aug - 18 Aug
Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (593)
"I would stay again. "
The price is £132
includes taxes & fees
25 Aug - 26 Aug
Sonder by Marriott Bonvoy South Wabash Apartments South Loop

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.8 out of 10, Good, (124)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
The price is £91
includes taxes & fees
24 Aug - 25 Aug
Sonder by Marriott Bonvoy The Plymouth Apartments Loop

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (322)
"Great stay"
Kasa South Loop Chicago

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (200)
"Clean, new, spacious "
The price is £185
includes taxes & fees
24 Aug - 25 Aug
Sonder by Marriott Bonvoy The Burnham Apartments Loop

The Neighborhood Hotel-Little Italy

4.0 star property
9.8 out of 10, Exceptional, (181)
"Great suite"
The Neighborhood Hotel-Little Italy

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very good, (169)
"Great location. Clean (very clean) and comfortable apartments with everything you need. Cons: soundproofing from the city center is weak, all sounds are heard quite well. In terms of price per room ratio - a super option. I will book next time, and I recommend it to everyone."
The price is £141
includes taxes & fees
17 Aug - 18 Aug
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (157)
"Great location and very clean! Will definitely be staying again. "
The price is £213
includes taxes & fees
4 Aug - 5 Aug
Kasa River North Chicago

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.6 out of 10, Excellent, (43)
"Great location. Apartment had all the amenities needed. Felt safe. Only not so good part was that being in downtown, it wasn't super quiet at times. Would stay here again without a doubt."
The price is £119
includes taxes & fees
17 Aug - 18 Aug
Sonder by Marriott Bonvoy The Opal Apartments River North

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
8.8 out of 10, Excellent, (56)
"Great location, easy stay!"
The price is £186
includes taxes & fees
24 Aug - 25 Aug
Sonder by Marriott Bonvoy Greektown Apartments

Huge Projector and Designated Workspace - Near Wrigley!

The price is £213
includes taxes & fees
12 Aug - 13 Aug
Huge Projector and Designated Workspace - Near Wrigley!

Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater

The price is £823
includes taxes & fees
18 Aug - 19 Aug
Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater

Your Perfect 2BR Home w/ Parking

8.0 out of 10, Very good, (1)
"Our stay was great, the apartment was close to the bus line and the train. The beds were very comfortable and it was a good size for our family. It was nice to have the off street parking in the back although the rear entrance was a bit disheveled. The building was secure but not entirely sound proof, but that is expected in a basement appartment. I would stay here again on a trip to Chicago. "
The price is £177
includes taxes & fees
4 Aug - 5 Aug
Your Perfect 2BR Home w/ Parking

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

8.0 out of 10, Very good, (2)
"Very nice place "
The price is £203
includes taxes & fees
11 Aug - 12 Aug
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.2 out of 10, Wonderful, (15)
"Its was in a good location for anyone who has family close by. Bed was wonderful. "
The price is £181
includes taxes & fees
4 Aug - 5 Aug
Ground Floor Studios in Chicago by 747 Lofts

Luxury Home Away From Your Home

9.0 out of 10, Wonderful, (124)
"Property manager was very responsive and the communication was clear and helpful. The house was very clean. Although the neighborhood was very concerning, dirty with a lot of people standing on the block, no one was threatening and nothing happened during our stay. Parking on street was safe. "
Luxury Home Away From Your Home

Spacious 3-bedroom apartment near downtown, FREE PARKING

10.0 out of 10, Exceptional, (1)
"Extremely clean space that was perfect for our group. We didn't spend a lot of time in the home during our stay, but when we did it was fantastic. Only minor gripe would be the upstairs neighbors, they were occasionally quite loud and woke us up a few times in the middle of the night. Would absolutely stay here again, if/when we come back to the area."
The price is £296
includes taxes & fees
4 Aug - 5 Aug
Spacious 3-bedroom apartment near downtown, FREE PARKING

Bright & Roomy 4BR in Pilsen

7.4 out of 10, Good, (6)
The price is £300
includes taxes & fees
12 Aug - 13 Aug
Bright & Roomy 4BR in Pilsen

Clarendon Hills Top Floor

7.2 out of 10, Good, (7)
"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
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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Top Darien Hotel Reviews

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?

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: 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 dishwasher, 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 Ty Warner Park. 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.