Darien holiday lettings

We found 302 holiday rentals — enter your dates for availability

Discover a selection of 8 homes and other holiday rentals in Darien that are perfect for your trip. Whether you're going on holiday with family or friends, holiday homes have the amenities that you expect for your stay, which might include a pool and a washer and dryer. No matter what you're looking for, you'll be sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Darien

Showing deals for:14 Nov - 21 Nov

Image gallery for Luxury 4-bedroom home in beautiful Willowbrook Forest Preserve area with AC WiFi

Private kitchen
10 out of 10 rating
Exceptional
(8 reviews)

Luxury 4-bedroom home in beautiful Willowbrook Forest Preserve area with AC WiFi

Willowbrook, IL

8% off
Price is £2,075
£296 per night
includes taxes & fees
Luxury 4-bedroom home in beautiful Willowbrook Forest Preserve area with AC WiFi

Find spaces that suit your style

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    Enjoy full kitchens, pools, gardens and more

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Find out more about Darien

Find out more about Darien

The picturesque setting of Darien is ready to explore

The area's temples and monuments are just some of the reasons to come on holiday to Darien. Renowned for its shopping, restaurants and basketball games, this city welcomes all visitors. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in and around Darien

Are you searching for attractions to see while you're in town? Venture out of your holiday home and experience everything that makes Darien a fun place to get away to. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Seven Bridges Golf Club (5.3 mi / 8.6 km)
  • Cog Hill Golf & Country Club (5.4 mi / 8.7 km)
  • Oak Brook Golf Course (6.8 mi / 10.9 km)
  • Galloping Ghost (7.7 mi / 12.4 km)
  • Bolingbrook Golf Club (10.6 mi / 17.1 km)
  • Cantigny Golf Club (11.6 mi / 18.6 km)

Exploring the natural landscape of Darien

Whether you're looking for adventure or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in Darien. These are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Morton Arboretum (6.2 mi / 9.9 km)
  • Riverwalk Park (9.5 mi / 15.3 km)
  • Centennial Beach (9.6 mi / 15.4 km)
  • Lake Katherine Nature Center (10 mi / 16 km)
  • Centennial Park (11.2 mi / 18 km)
  • Garfield Park (16.1 mi / 26 km)

Travelling to and around Darien

The nearest airport is in Chicago Midway Airport (MDW), located 12.3 mi (19.8 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into Chicago O'Hare International Airport (ORD), which is 16.2 mi (26.1 km) away.

Frequently asked questions

What is the best area to stay in Darien when booking a holiday rental?
When considering a holiday rental in Darien, Illinois, one of the most appealing areas to stay is near the Darien Sportsplex. This vibrant neighbourhood not only offers a range of properties, with several options available for families and solo travellers alike, but it also provides easy access to various recreational activities. The Sportsplex itself is a fantastic attraction, featuring ice skating, indoor soccer, and other sports facilities that can entertain visitors of all ages.

Another lovely area to consider is the vicinity of the Waterfall Glen Forest Preserve. This picturesque location is great for those who enjoy the outdoors, boasting miles of scenic trails ideal for hiking, biking, and nature walks. The preserve is well-loved by both locals and visitors, making it a delightful spot to explore the natural beauty of the region. The presence of numerous rental properties nearby ensures that you can find a comfortable base from which to enjoy these attractions.
How much does it cost to rent a holiday home in Darien?
Prices for holiday rentals in Darien vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Darien to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Darien holiday house rentals?
You can find great discounts on house rentals in Darien on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of holiday rental accomodation in Darien?
In Darien, holiday houses are the most popular type of accommodation, with several available throughout the area. These properties typically offer spacious living arrangements, featuring multiple bedrooms, fully equipped kitchens, and comfortable living areas. Many also come with outdoor spaces such as gardens or patios, great for enjoying the suburban surroundings. The holiday houses in Darien provide an inviting space for families or groups looking for a home-like experience while exploring the nearby attractions and parks.
Are there any family house rentals in Darien?
In Darien, Illinois, there are several family-friendly house rentals available, making it a suitable destination for those travelling with children. This suburban area offers spacious homes with amenities that cater to families, such as fully equipped kitchens for preparing family meals, comfortable living rooms for relaxation, and outdoor spaces for kids to play.
Can I find long-stay holiday rentals in Darien?
A long-stay holiday rental in Darien is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Darien?
In Darien, Illinois, there are several pet-friendly house rentals available for travellers. Many of these properties come equipped with amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups travelling with pets. The area offers a variety of styles, from modern single-family homes to charming bungalows, ensuring options to suit different preferences and budgets.
Are there any remote work holiday rentals in Darien?
In Darien, Illinois, there are several remote work holiday rentals available, making it a suitable destination for those looking to combine work and leisure. Many of these properties come equipped with strong Wi-Fi connections, dedicated workspaces, and comfortable living areas, allowing for an efficient work environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Darien holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Darien with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Darien?
In Darien, popular rental amenities include kitchens, allowing guests to prepare their own meals during their stay. Many properties also permit pets, making it a great choice for travellers with furry companions. Additionally, some rentals offer features tailored for service animals, such as waiver of fees.
When is the best time to visit Darien for a holiday rental?
The most popular time to visit Darien is from May to July, when the weather is warm and the area comes alive with activities. This peak season attracts families and holidaymakers looking to enjoy the vibrant local parks, outdoor festivals, and community events that characterise the region. With temperatures typically ranging from 20 to 30 degrees Celsius, it's an ideal time for enjoying picnics, walks, and various recreational activities in the sunshine.

July stands out as the busiest month, offering plenty of opportunities for sightseeing and enjoying the local culture. Visitors can take advantage of the pleasant weather to explore attractions like the nearby Morton Arboretum or embark on day trips to Chicago, just a short drive away.

For those considering a more budget-friendly option, November is a fantastic time to visit Darien. Although this month sees fewer tourists, it still presents a lovely atmosphere for exploring the area. You can enjoy quieter parks, take in the autumn colours, and appreciate the local community without the hustle and bustle of peak season.
How early should I book a Darien holiday rental?
Book your Darien holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Darien home rental booking on Vrbo?
To find Darien holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Darien holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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