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Hillside holiday lettings

We found 643 holiday rentals — enter your dates for availability

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August 2025

September 2025

Scroll through and select from holiday rentals in Hillside to find one that's perfect for your trip. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll have the best amenities for spending time at your home away from home, which might include parking and a washer and dryer. No matter what you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Hillside

Showing deals for:7 Nov - 14 Nov

This home is breathtaking. Several guests have said this is a 10 star home

Exceptional

(30 reviews)

5 Star Upscale Entire Family Neighborhood Home

Berwyn, IL

8% off

£292 per night

includes taxes & fees

Exceptional

(9 reviews)

Oak Park IL · Charming Retro 2BR Cottage/Train/Laundry/FREE PKG

Oak Park, IL

6% off

£147 per night

includes taxes & fees

Indulge in lavish outdoor living with ample seating, firepit, and daybed.

Exceptional

(5 reviews)

Modern 3-Bed Stay w/ Patio & Firepit, 15 Minutes to Downtown

Chicago, IL

11% off

£267 per night

includes taxes & fees

We are proud that our home boasts one of the largest yards in all of Chicago!

Exceptional

(16 reviews)

Luxe Duplex - Private Gym -Huge Yard -King Beds Garage Parking-EV Charger- Crib

Chicago, IL

24% off

£217 per night

includes taxes & fees

Exceptional

(11 reviews)

PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard

Lombard, IL

8% off

£214 per night

includes taxes & fees

Exceptional

(9 reviews)

Elegantly decorated spacious 4 bedroom, 5 bathroom home in historic Oak Park

Oak Park, IL

7% off

£761 per night

includes taxes & fees

Exceptional

(5 reviews)

Spacious 5BR, Game Room, Free Parking, Fenced Yard, Near Hwy & Public Transit

Oak Park, IL

11% off

£613 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Hillside

Spacious clean full apartment 20 min from downtown chicago

Sleeps 3 · 1 bedroom · 1 bathroom

Step into the Past: Stylish 1970s Mid-Century VRBO for a Vintage Getaway!

Sleeps 8 · 3 bedrooms · 2 bathrooms

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

Sleeps 10 · 4 bedrooms · 2+ bathrooms

Short Drive from Cernan Earth & Space Center! Kitchen, Free Airport Shuttle!

Sleeps 2 · 1 bedroom · 1 bathroom

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Enjoy full kitchens, pools, gardens and more
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More space, more privacy, more amenities — more value

Find out more about Hillside

The relaxing area of Hillside awaits your stay

Enjoy the live music and other features of Hillside. Travellers especially like the shopping, restaurants and forests in this relaxing and welcoming city. Wrigley Field and Michigan Avenue are just a couple of the must-see attractions in the area. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in Hillside

Are you looking for attractions to visit while you're in town? Venture out of your cosy holiday rental and experience everything that Hillside has to offer. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

Galloping Ghost (4.9 mi / 7.8 km)
LEGOLAND® Discovery Center (13.1 mi / 21 km)
Cantigny Golf Club (13.2 mi / 21.2 km)
Dave & Buster's (14.1 mi / 22.6 km)
Lincoln Park Zoo (14.2 mi / 22.8 km)
Cog Hill Golf & Country Club (14.4 mi / 23.2 km)

Exploring the natural landscape of Hillside

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Hillside is a great place to get outside. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

Millennium Park (14.4 mi / 23.2 km)
Grant Park (14.5 mi / 23.4 km)
Morton Arboretum (8.6 mi / 13.9 km)
Portage Park (8.9 mi / 14.3 km)
Garfield Park (9.5 mi / 15.3 km)
Garfield Park Conservatory (9.6 mi / 15.4 km)

Travelling to and around Hillside

The nearest airport is in Chicago O'Hare International Airport (ORD), located 6.9 mi (11 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into Chicago Midway Airport (MDW), which is 10.4 mi (16.7 km) away.

Frequently asked questions

What is the best area to stay in Hillside when booking a holiday rental?

When considering a holiday rental in Hillside, Illinois, one of the most appealing areas to stay is near the vicinity of the Hillside Town Centre. This neighbourhood offers a charming blend of local amenities and convenient access to various attractions. Staying here gives you the advantage of being close to the Hillside Memorial Park, a lovely space for leisurely walks and picnics. Additionally, the nearby Brookfield Zoo is a must-visit, renowned for its impressive collection of animals and engaging exhibits, making it a great day out for families and animal lovers alike.

How much does it cost to rent a holiday home in Hillside?

Prices for holiday rentals in Hillside 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 Hillside 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 Hillside holiday house rentals?

You can find great discounts on house rentals in Hillside 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.

Can I find long-stay holiday rentals in Hillside?

A long-stay holiday rental in Hillside 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 any Hillside holiday rentals with parking?

Vrbo offers a wide selection of holiday rentals in Hillside 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.

When is the best time to visit Hillside for a holiday rental?

The most popular time to visit Hillside, Illinois, is during the peak season from May to July, when the warm weather beckons outdoor enthusiasts and families alike to explore the area's attractions. This vibrant period brings a lively atmosphere, great for those looking to partake in local festivals, outdoor events, and the nearby attractions of Chicago, which is just a short drive away.

July stands out as the most sought-after month, with temperatures typically reaching the high 20s Celsius, making it ideal for enjoying parks, picnics, and a variety of recreational activities. Visitors often take advantage of the comfortable climate to explore the beautiful landscapes and partake in local events, ensuring a memorable holiday experience.

For those seeking a more budget-friendly option, November offers a quieter and more relaxed atmosphere. While the weather cools down to the low single digits Celsius, visitors can enjoy the charm of the area with fewer crowds, allowing for leisurely strolls and a chance to experience local culture at a more intimate pace.

How early should I book a Hillside holiday rental?

Book your Hillside 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 Hillside home rental booking on Vrbo?

To find Hillside 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 Hillside 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.