Darien Holiday Rentals

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Holiday Rentals in Darien

Sentral Michigan Avenue

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (983)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is NZ$296
includes taxes & fees
7 Dec - 8 Dec
Sentral Michigan Avenue

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
Downtown Chicago
8.0 out of 10, Very good, (401)
"Quite and low key spot"
United States
Shunica
Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Kasa South Loop Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (373)
"An excellent place to stay in Chicago downtown."
United States
ABDULHAFEEZ
Kasa South Loop Chicago

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
Near South Side
8.6 out of 10, Excellent, (713)
"Love the unit and location close to multiple restaurants and shopping."
United States
Jessie
Sonder by Marriott Bonvoy South Wabash Apartments South Loop

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (253)
"Great stay. "
United States
Teresa
Sonder by Marriott Bonvoy The Burnham Apartments Loop

The Neighborhood Hotel-Little Italy

4.0 star property
Near West Side
9.6 out of 10, Exceptional, (218)
"This hotel is a 10 out of 10 for me! The hotel room was clean and the location was great. When I come back next year I’m definitely coming back here "
United States
Amonee
The Neighborhood Hotel-Little Italy

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
Downtown Chicago
8.4 out of 10, Very good, (57)
"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."
United States
Swastika
Sonder by Marriott Bonvoy The Opal Apartments River North

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
Downtown Chicago
8.2 out of 10, Very good, (188)
"Place was amazing! Very centralized, all sorts of restaurants nearby, and right next to the CTA Trains which is AWESOME!"
United States
Alexander
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Kasa River North Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (178)
"Awesome stay "
United States
Sally
Kasa River North Chicago

Chicago luxury home suites

2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"This was Amazing stay I have ever had in my life. Wonderful host, super clean. Stunning views, close to everything that you would needed. "
New Zealand
Moha
The price is NZ$586
includes taxes & fees
17 Nov - 18 Nov
Chicago luxury home suites

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (65)
"I enjoyed my stay! Thanks!"
United States
Jonathan
Sonder by Marriott Bonvoy Greektown Apartments

Stylish Apartment near Chicago Downtown

2.0 star property
Bridgeport
The price is NZ$668
includes taxes & fees
17 Nov - 18 Nov
Stylish Apartment near Chicago Downtown

Cozy Studio in Hyde Park-Walk to Lake & University

Hyde Park
8.8 out of 10, Excellent, (10)
"Good communication and easy check-in"
United States
Chen
The price is NZ$283
includes taxes & fees
3 Dec - 4 Dec
Cozy Studio in Hyde Park-Walk to Lake & University

3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

Near West Side
10.0 out of 10, Exceptional, (265)
"Extremely well equipped amenities, towels,etc. Excellent linens and bed coverings."
United States
RICHARD W.
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

Stylish 1BR in West Loop

Downtown Chicago
10.0 out of 10, Exceptional, (9)
"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"
United States
Jacob D.
The price is NZ$315
includes taxes & fees
19 Nov - 20 Nov
Stylish 1BR in West Loop

Art Villa

5.0 star property
West Town
10.0 out of 10, Exceptional, (2)
" "
United States
tomonobu
The price is NZ$1,774
includes taxes & fees
17 Nov - 18 Nov
Art Villa

Remodeled West Loop Apartment Near United Center

Near West Side
9.0 out of 10, Wonderful, (56)
"Overall it was a great stay. My family has special dietary needs so we need to be able to cook a few meals at wherever we stay to be on the safe side, so the fully equipped kitchen was a definite plus. Had some rowdy neighbors to the building next to us, but what can you do. We look forward to visiting Chicago again soon."
United States
Brittney D.
Remodeled West Loop Apartment Near United Center

NEW LUXURY PENTHOUSE CONDO

West Town
10.0 out of 10, Exceptional, (199)
"I cannot recommend this property enough! Easiest check-in/out ever. Excellent communication from the host. And the condo itself was fabulous! The area was so quiet and peaceful, it was hard to believe we were in a city the size of Chicago. Having a lot private garage was"
United States
Stacey
NEW LUXURY PENTHOUSE CONDO

Experience Chicago living near United Center

Austin
9.2 out of 10, Wonderful, (27)
"overall place is good, the only bad thing is the location!"
United States
rebecca w.
Experience Chicago living near United Center

Twice as Nice: Chic 2BR Stay with Style & Space

Downtown Chicago
9.6 out of 10, Exceptional, (13)
"Had a very nice time in Chicago!"
United States
Valerie S.
The price is NZ$389
includes taxes & fees
1 Dec - 2 Dec
Twice as Nice: Chic 2BR Stay with Style & Space
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

Everything you need to know about Darien holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Darien holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Darien holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Darien holiday rentals we have selected for you start as low as NZ$283 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 holiday 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 holiday.

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 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 offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

How many holiday rentals are there in Darien?

Choose from 7 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.