Darien Vacation Rentals

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Vacation Rentals in Darien

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (896)
"great food spots all around and beautiful sites to see "
The price is CA $198
CA $272 total
includes taxes & fees
Sep 3 - Sep 4
Sentral Michigan Avenue

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.2 out of 10, Very good, (350)
"Great stay!"
The price is CA $177
CA $208 total
includes taxes & fees
Sep 1 - Sep 2
Sonder by Marriott Bonvoy Market Hall Apartments West Loop

The Neighborhood Hotel-Little Italy

4.0 star property
9.6 out of 10, Exceptional, (193)
"Property was extremely comfortable in a great area."
The Neighborhood Hotel-Little Italy

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (633)
"Loved this apartment style stay near everything we wanted to visit in Chicago. "
The price is CA $177
CA $208 total
includes taxes & fees
Sep 3 - Sep 4
Sonder by Marriott Bonvoy South Wabash Apartments South Loop

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (208)
"Great location, room was very nice. Vent in the bathroom wasn’t working and the walls are paper thin so you can hear other people talking loud. Otherwise a great stay! "
The price is CA $210
CA $246 total
includes taxes & fees
Sep 14 - Sep 15
Sonder by Marriott Bonvoy The Burnham Apartments Loop

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (333)
"Great stay"
Kasa South Loop Chicago

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very good, (177)
"Great location!!!"
The price is CA $205
CA $241 total
includes taxes & fees
Sep 3 - Sep 4
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.4 out of 10, Very good, (47)
"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 CA $233
CA $273 total
includes taxes & fees
Sep 28 - Sep 29
Sonder by Marriott Bonvoy The Opal Apartments River North

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (166)
"Great location and very clean! Will definitely be staying again. "
The price is CA $206
CA $340 total
includes taxes & fees
Sep 2 - Sep 3
Kasa River North Chicago

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.8 out of 10, Good, (132)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
The price is CA $260
CA $305 total
includes taxes & fees
Sep 1 - Sep 2
Sonder by Marriott Bonvoy The Plymouth Apartments Loop

Art Villa

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
The price is CA $1,031
CA $1,706 total
includes taxes & fees
Sep 1 - Sep 2
Art Villa

Cozy Studio in Hyde Park-Walk to Lake & University

10.0 out of 10, Exceptional, (2)
"This place was nice and clean and close to what I needed to do. I appreciated that it was affordable. "
The price is CA $127
CA $265 total
includes taxes & fees
Sep 1 - Sep 2
Cozy Studio in Hyde Park-Walk to Lake & University

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

6.0 out of 10, (2)
"Great space for large groups. Park across the street is a great "feature"."
The price is CA $214
CA $1,259 total
includes taxes & fees
Sep 23 - Sep 24
Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater

Prime City Stay in a 1BR Apt

9.2 out of 10, Wonderful, (9)
The price is CA $117
CA $267 total
includes taxes & fees
Sep 7 - Sep 8
Prime City Stay in a 1BR Apt

Stylish 1BR in West Loop

10.0 out of 10, Exceptional, (5)
The price is CA $168
CA $328 total
includes taxes & fees
Sep 1 - Sep 2
Stylish 1BR in West Loop

Amazing 3-bedroom house with WiFi and AC in awesome Chicago

Amazing 3-bedroom house with WiFi and AC in awesome Chicago

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
8.6 out of 10, Excellent, (59)
"loved our stay there. close to UIC and Greektown. will stay again"
The price is CA $291
CA $342 total
includes taxes & fees
Sep 28 - Sep 29
Sonder by Marriott Bonvoy Greektown Apartments

Central Haven Escape: Stylish 3BR With Free Parking

6.8 out of 10, (6)
"The overall experience was surprisingly great. We were a little worried after reading some bad reviews because of the house smelling like smoke. It didn’t. In fact, it smelled super clean and fresh. It is a cute little, older, clean 3 bedroom apartment above a building in a downtown neighborhood. So cute!"
Central Haven Escape: Stylish 3BR With Free Parking

Bright & Roomy 4BR in Pilsen

8.0 out of 10, Very good, (8)
The price is CA $163
CA $410 total
includes taxes & fees
Sep 2 - Sep 3
Bright & Roomy 4BR in Pilsen

Your Perfect 2BR Home w/ Parking

8.4 out of 10, Very good, (6)
"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 CA $151
CA $350 total
includes taxes & fees
Sep 1 - Sep 2
Your Perfect 2BR Home w/ Parking
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

Find out more about Darien

Find out more about Darien

Everything you need to know about Darien vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Darien vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Darien vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Darien vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Darien. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Darien vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Darien vacation rentals we have selected for you start as low as CA $117 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Darien rentals

At Expedia, we put the best Darien vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Darien rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Darien vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Darien. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a vacation rental in Darien?

Yes, we give you a choice of vacation rentals close to top local attractions in Darien, or you can go with a secluded option if you want a relaxing place to 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's the top vacation rental in Darien?

Amazing 3-bedroom house with WiFi and AC in awesome Chicago: This vacation home rental near Darien has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many vacation rentals are there in Darien?

Choose from 7 Expedia vacation rentals in Darien for a memorable vacation.

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 larger area, you’ll find National Shrine of St. Therese and Burr Ridge Village Center.

What are vacation rentals like in Darien?

Vacation rentals are private accommodations you can reserve for a few days or a quick weekend in Darien. Vacation rentals feature extras such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from shared hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for a family trip.