Hillside holiday rentals

We found 723 holiday rentals — enter your dates for availability
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:15 Jan - 22 Jan

Living area
Dining
Living area
Private kitchen
Exceptional
(17 reviews)

Elegant Escape by Downtown Burr Ridge with an easy access to Chicago Landmarks

Burr Ridge

8% off
AU$5,521
for 7 nights, 1 home
AU$789 per night
includes taxes & fees
Elegant Escape by Downtown Burr Ridge with an easy access to Chicago Landmarks
Living area
Dining
Private kitchen
Room
Exceptional
(11 reviews)

Quick Access to O'Hare and Chicago downtown

Melrose Park

8% off
AU$3,483
for 7 nights, 1 home
AU$498 per night
includes taxes & fees
Quick Access to O'Hare and Chicago downtown
Dining
Exterior
Private kitchen
Interior
Exceptional
(27 reviews)

Beautiful Berwyn Bungalow Close to Downtown Chicago

Berwyn

8% off
AU$3,445
for 7 nights, 1 home
AU$492 per night
includes taxes & fees
Beautiful Berwyn Bungalow Close to Downtown Chicago
Private kitchen
Property grounds
Room
Living area
Exceptional
(8 reviews)

Rare Historic One Bedroom Carriage House in Downtown Glen Ellyn

Glen Ellyn

8% off
AU$2,358
for 7 nights, 1 room
AU$337 per night
includes taxes & fees
Rare Historic One Bedroom Carriage House in Downtown Glen Ellyn
Fully fenced yard - perfect for fur babies
Breakfast bar seating also available
Open concept kitchen
Master bedroom w/king size memory foam bed
Exceptional
(25 reviews)

Wonderful in Wood Dale, right by O’Hare airport!

Wood Dale

13% off
AU$4,120
for 7 nights, 1 home
AU$589 per night
includes taxes & fees
Wonderful in Wood Dale, right by O’Hare airport!
Interior
Private kitchen
Terrace/patio
Living area
Wonderful
(17 reviews)

French Country Cottage in lovely Glen Ellyn!

Glen Ellyn

8% off
AU$7,091
for 7 nights, 1 home
AU$1,013 per night
includes taxes & fees
French Country Cottage in lovely Glen Ellyn!
Private kitchen
Room
Dining
Terrace/patio
Exceptional
(24 reviews)

Luxe Duplex - Private Gym -Huge Backyard -Arcade- King Beds - Garage-EV Charger

Chicago

22% off
AU$2,949
for 7 nights, 1 home
AU$421 per night
includes taxes & fees
Luxe Duplex - Private Gym -Huge Backyard -Arcade- King Beds - Garage-EV Charger
Room
Interior
Living area
Living area
Exceptional
(25 reviews)

Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT

Berwyn

8% off
AU$1,433
for 7 nights, 1 apartment
AU$205 per night
includes taxes & fees
Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT
Living area
Dining
Living area
Private kitchen
Exceptional
(7 reviews)

Modern 4-bedroom house in peaceful Westmont area

Westmont

8% off
AU$4,534
for 7 nights, 1 home
AU$648 per night
includes taxes & fees
Modern 4-bedroom house in peaceful Westmont area
The sunroom overlooks the fountain courtyard. A peaceful place to unwind.
The Davis House is set in a park like setting providing privacy
The library with the connecting powder room. It has an original swinging door.
Property grounds
Exceptional
(183 reviews)

Charming Victorian Farm house with large eat in kitchen in Historic Glen Ellyn.

Glen Ellyn

6% off
AU$3,229
for 7 nights, 1 home
AU$461 per night
includes taxes & fees
Charming Victorian Farm house with large eat in kitchen in Historic Glen Ellyn.
Living area
Interior
Private kitchen
Room
Wonderful
(41 reviews)

Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP

Berwyn

8% off
AU$1,764
for 7 nights, 1 apartment
AU$252 per night
includes taxes & fees
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
Living area
Private kitchen
Living area
Dining
Excellent
(6 reviews)

Gorgeous 7BD Home w/ Garage

Chicago

8% off
AU$6,788
for 7 nights, 1 home
AU$970 per night
includes taxes & fees
Gorgeous 7BD Home w/ Garage
Private kitchen
Living area
Living area
Exterior
Excellent
(11 reviews)

Spacious / New - 8BD/4BTH - Sleeps 16 + Garage!

Chicago

8% off
AU$6,787
for 7 nights, 1 home
AU$970 per night
includes taxes & fees
Spacious / New - 8BD/4BTH - Sleeps 16 + Garage!
Room
Living area
Dining
Private kitchen
Very good
(5 reviews)

Chicago style apt/Near Hosp/ORD/MDW/DT

Berwyn

8% off
AU$1,563
for 7 nights, 1 apartment
AU$223 per night
includes taxes & fees
Chicago style apt/Near Hosp/ORD/MDW/DT
Private kitchen
Dining
Living area
Living area
Wonderful
(21 reviews)

Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI

Berwyn

8% off
AU$1,517
for 7 nights, 1 apartment
AU$217 per night
includes taxes & fees
Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI
Room
Living area
Interior
Private kitchen
Exceptional
(23 reviews)

Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW

Berwyn

8% off
AU$1,470
for 7 nights, 1 apartment
AU$210 per night
includes taxes & fees
Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
Queen Room opens up to a sun room / office
Night View
The side view
A Viking Stove and Quartz Countertops, You decide whats cooking.
Exceptional
(26 reviews)

First floor of Historic Oak Park Villa, Grge:2Cars

Oak Park

11% off
AU$1,689
for 7 nights, 1 apartment
AU$241 per night
includes taxes & fees
First floor of Historic Oak Park Villa, Grge:2Cars
Multiple parks for kids just a few blocks away
Master Bedroom with King Size Bed
The light corridor combines connection with privacy.
Cheney Mansion 4 min walk
Exceptional
(24 reviews)

Top floor of Historic Oak Park Home /2 Car Garage

Oak Park

11% off
AU$1,674
for 7 nights, 1 apartment
AU$239 per night
includes taxes & fees
Top floor of Historic Oak Park Home /2 Car Garage
Interior detail
Living area
Dining
Room
Exceptional
(14 reviews)

Ridgeland Retreat/ Street level Apt easy access

Berwyn

8% off
AU$2,162
for 7 nights, 1 apartment
AU$309 per night
includes taxes & fees
Ridgeland Retreat/ Street level Apt easy access
Exterior detail
Private kitchen
Interior
Living area
Exceptional
(16 reviews)

Large Renovated 1st FL Suite Forest Park/Oak Park

Forest Park

11% off
AU$1,986
for 7 nights, 1 apartment
AU$284 per night
includes taxes & fees
Large Renovated 1st FL Suite Forest Park/Oak Park
Bathroom
Room
Dining
Living area
Exceptional
(14 reviews)

Chic & Cozy near ORD>MDW>DT>HOSP

Berwyn

8% off
AU$1,848
for 7 nights, 1 apartment
AU$264 per night
includes taxes & fees
Chic & Cozy near ORD>MDW>DT>HOSP
Room
Dining
Dining
Living area
Exceptional
(35 reviews)

Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

Berwyn

8% off
AU$1,598
for 7 nights, 1 apartment
AU$228 per night
includes taxes & fees
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
Room
Living area
Private kitchen
Miscellaneous
Exceptional
(8 reviews)

Cozy 2-bedroom 15 min to downtown Chicago

Cicero

8% off
AU$2,174
for 7 nights, 1 apartment
AU$311 per night
includes taxes & fees
Cozy 2-bedroom 15 min to downtown Chicago
Private kitchen
Dining
Exterior
Living area
Exceptional
(41 reviews)

Clean and Comfy Updated Apt in Convenient Location

Forest Park

8% off
AU$1,823
for 7 nights, 1 apartment
AU$260 per night
includes taxes & fees
Clean and Comfy Updated Apt in Convenient Location
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

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 Soldier Field 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:

  • Oak Brook Golf Course (2.9 mi / 4.7 km)
  • Galloping Ghost (4.9 mi / 7.8 km)
  • The Dome at the Parkway Bank Sports Complex (7.3 mi / 11.7 km)
  • LEGOLAND® Discovery Center (13.1 mi / 21 km)
  • Cantigny Golf Club (13.2 mi / 21.2 km)
  • Lincoln Park Zoo (14.2 mi / 22.8 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

When is the best time to visit Hillside for a holiday rental?
The peak season in Hillside runs from May to July, making this the most popular time for holiday rentals as families and adventure-seekers flock to the area. July, in particular, shines with its vibrant summer atmosphere, offering a variety of local festivals and outdoor activities that cater to all ages. The pleasant temperatures, averaging around 25 to 30 degrees Celsius, create an inviting environment for exploring the nearby parks, engaging in outdoor sports, or simply enjoying leisurely strolls through the charming neighbourhoods.For those considering a visit during the quieter months, November presents a wonderful opportunity to experience Hillside at a more relaxed pace. While the weather might be cooler, typically ranging from 0 to 10 degrees Celsius, this month allows you to enjoy the local culture and attractions without the hustle and bustle of peak tourist activity. Plus, you'll find that holiday rentals are often more affordable during this time, providing excellent value for your stay.Ultimately, your decision on when to visit Hillside should hinge on your preferences for lively summer activities or a tranquil escape in the autumn months.
What are the top attractions in Hillside?
In Hillside, Illinois, visitors can explore several attractions that showcase the charm of the area. The nearby Brookfield Zoo is a major highlight, offering a variety of animal exhibits and family-friendly activities, making it a great spot for a day out. Just a short drive away, the Oak Brook Shopping Centre provides a more upscale retail experience with a range of shops and dining options.For those interested in history, the Hillside Historical Museum offers insights into the local heritage, while the beautiful parks in the area, such as the Hillside Park, provide ample opportunities for outdoor activities, including walking trails and picnic areas.
Are all fees included in the Hillside holiday homes prices shown on Stayz?
Stayz 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.
Are there any Hillside holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Hillside holiday homes?
You can find great discounts on holiday homes in Hillside on Stayz, 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 change or cancel my Hillside holiday home booking on Stayz?
To find Hillside holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Hillside?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Hillside holiday home?
Book your Hillside holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Hillside?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Hillside to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

More holiday ideas