Holiday Rentals in Darien

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Holiday Rentals in Darien

Aparthotel in Downtown Chicago

4.0 star property
9.2 out of 10, Wonderful, (988)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is €128
includes taxes & fees
7 Dec - 8 Dec
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

4.0 star property
9.4 out of 10, Exceptional, (376)
"An excellent place to stay in Chicago downtown."
United States
ABDULHAFEEZ
Kasa South Loop Chicago

Aparthotel in Near West Side

4.0 star property
9.6 out of 10, Exceptional, (219)
"Staff was courteous. Great location."
United States
Pamela
The Neighborhood Hotel-Little Italy

Aparthotel in Downtown Chicago

4.0 star property
9.4 out of 10, Exceptional, (179)
"Awesome stay "
United States
Sally
Kasa River North Chicago

Aparthotel in Downtown Chicago

2.0 star property
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 €305
includes taxes & fees
23 Nov - 24 Nov
Chicago luxury home suites

Aparthotel in Bridgeport

2.0 star property
The price is €343
includes taxes & fees
7 Dec - 8 Dec
Stylish Apartment near Chicago Downtown

Aparthotel in West Town

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
United States
tomonobu
Art Villa

Apartment in 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 €142
includes taxes & fees
7 Dec - 8 Dec
Stylish 1BR in West Loop

Apartment in Near West Side

10.0 out of 10, Exceptional, (268)
"Lovely place! Very clean and has all of the amenities necessary for a good stay. Lots of fresh towels, a fully stocked kitchen and the location is excellent. "
United States
Angela C.
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

Apartment in Near West Side

9.0 out of 10, Wonderful, (56)
"This apartment is very close to downtown with easy parking right outside! The unit is very well maintained with spacious rooms and amenities! The host has thought of everything to make it feel like your own home! Would love to come back and stay here again!"
United States
kiran
Remodeled West Loop Apartment Near United Center

Condo in West Town

10.0 out of 10, Exceptional, (200)
"Great house with a great rooftop. "
United States
Francisco
NEW LUXURY PENTHOUSE CONDO

Apartment in Downtown Chicago

9.6 out of 10, Exceptional, (14)
"Had a very nice time in Chicago!"
United States
Valerie S.
The price is €164
includes taxes & fees
30 Nov - 1 Dec
Twice as Nice: Chic 2BR Stay with Style & Space

Condo in Austin

9.2 out of 10, Wonderful, (28)
"We were in town with our rowing team for a regatta, and this was a perfect spot to stay! Amenities were perfect for our needs, the living room is super spacious for some morning yoga, and the owners were responsive to any questions we had. Will definitely be saving this location for our trip here next year?"
United States
McKenzie J.
Experience Chicago living near United Center

Apartment in Blue Island

7.6 out of 10, Good, (4)
"Only issue was the water pressure in the bathroom was very very low. "
United States
Derrick M.
The price is €244
includes taxes & fees
25 Nov - 26 Nov
Charming 2-bedroom apartment in marvelous Blue Island with WiFi

Holiday Home in Shorewood

2.5 star property
The price is €541
includes taxes & fees
24 Nov - 25 Nov
Modern 4 Bedroom Private Vacation Home

Condo in Austin

8.6 out of 10, Excellent, (21)
"Immaculately clean property"
United States
cody m.
Experience Chicago living near United Center

Aparthotel in West Town

2.0 star property
9.0 out of 10, Wonderful, (21)
"The stay lacked in shelf space as well as other amenities that could be useful. "
United States
Zugeily
Ground Floor Studios in Chicago by 747 Lofts

Holiday Home in Maywood

7.8 out of 10, Good, (13)
"Very nice place "
United States
Elliot H.
The price is €216
includes taxes & fees
23 Nov - 24 Nov
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Mobile Home in Burr Ridge

10.0 out of 10, Exceptional, (33)
"Nice stay. Dog friendly. Great location. Helpful and communicative owners. Well laid out tiny home. "
United States
Laura P.
The price is €163
includes taxes & fees
2 Dec - 3 Dec
Less is more! Pet friendly Tiny Home near Chicago!

Apartment in Downers Grove

9.6 out of 10, Exceptional, (30)
"My husband and I made a quick 2 night 3 day trip to Chicago to visit our daughter. Denise was a wonderful host and the space was perfect for 2. Thank you for a great stay. "
United States
Lisa & Jason M.
The price is €95
includes taxes & fees
23 Nov - 24 Nov
Pet Friendly-Cozy 1-bedroom apartment just 6 minutes drive to Morton Arboretum
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, apart-hotels, 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 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 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.