Oakbrook Terrace holiday rentals

We found 518 holiday rentals — enter your dates for availability
Discover a selection of 5 flats and other holiday rentals in Oakbrook Terrace that are perfect for your trip. Holiday homes offer the amenities that you expect for you and your friends, family or even pets, such as parking and a fireplace. No matter what you're looking for, you're sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Oakbrook Terrace

Showing deals for:15 Jan - 22 Jan

Private kitchen
Dining
Living area
Living area
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
Private kitchen
Dining
Living area
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
Interior
Private kitchen
Exceptional
(26 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
Terrace/patio
Room
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
Master bedroom w/king size memory foam bed
Breakfast bar seating also available
Fully fenced yard - perfect for fur babies
Interior
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!
Living area
Interior
Room
Living area
Exceptional
(25 reviews)

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

Berwyn

8% off
AU$1,440
for 7 nights, 1 apartment
AU$206 per night
includes taxes & fees
Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT
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.
Front entrance hall off of the beautiful front porch. The parlor is off of this.
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
Dining
Room
Wonderful
(41 reviews)

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

Berwyn

8% off
AU$1,765
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
Terrace/patio
Dining
Wonderful
(17 reviews)

French Country Cottage in lovely Glen Ellyn!

Glen Ellyn

8% off
AU$7,072
for 7 nights, 1 home
AU$1,010 per night
includes taxes & fees
French Country Cottage in lovely Glen Ellyn!
Living area
Dining
Room
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
Room
Living area
Dining
Interior
Exceptional
(23 reviews)

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

Berwyn

8% off
AU$1,473
for 7 nights, 1 apartment
AU$210 per night
includes taxes & fees
Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
Private kitchen
Living area
Interior
Room
Very good
(5 reviews)

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

Berwyn

8% off
AU$1,557
for 7 nights, 1 apartment
AU$222 per night
includes taxes & fees
Chicago style apt/Near Hosp/ORD/MDW/DT
Room
Private kitchen
Dining
Interior
Exceptional
(11 reviews)

Prime Location - Cozy Naperville HomeStay - GameRoom

Naperville

8% off
AU$2,868
for 7 nights, 1 home
AU$410 per night
includes taxes & fees
Prime Location - Cozy Naperville HomeStay - GameRoom
Queen Room opens up to a sun room / office
Night View
The side view
Magnificent tunes
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
Living Roo: The oak floors of this historic home give the living room a cozy, yet elegant feel. The room holding a 55 Inch TV, Gig Speed Internet and Mini Pool Table overlooks Oak Park Avenue .
Master Bedroom with King Size Bed
Multiple parks for kids just a few blocks away
The light corridor combines connection with privacy.
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
Exterior detail
Private kitchen
Living area
Interior
Exceptional
(16 reviews)

Large Renovated 1st FL Suite Forest Park/Oak Park

Forest Park

11% off
AU$2,013
for 7 nights, 1 apartment
AU$288 per night
includes taxes & fees
Large Renovated 1st FL Suite Forest Park/Oak Park
Room
Dining
Private kitchen
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
Living area
Private kitchen
Room
Private kitchen
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
Private kitchen
Room
Living area
Bathroom
Exceptional
(14 reviews)

Chic & Cozy near ORD>MDW>DT>HOSP

Berwyn

8% off
AU$1,839
for 7 nights, 1 apartment
AU$263 per night
includes taxes & fees
Chic & Cozy near ORD>MDW>DT>HOSP
Room
Dining
Dining
Interior
Exceptional
(34 reviews)

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

Berwyn

8% off
AU$1,596
for 7 nights, 1 apartment
AU$228 per night
includes taxes & fees
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
Private kitchen
Dining
Exterior
Property grounds
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

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    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

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  • 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 friendly area of Oakbrook Terrace awaits your stay

The area's entertainment and opera are just some of the reasons to come on holiday to Oakbrook Terrace. This welcoming and relaxing city is well known for its shopping, restaurants and zoo. Donald E. Stephens Convention Center and United Center are just a couple of the must-see attractions in the area. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in Oakbrook Terrace

Are you hoping to discover things to do in the area? Venture out of your holiday home and check out everything that Oakbrook Terrace has to offer. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Oak Brook Golf Course (2.4 mi / 3.9 km)
  • Galloping Ghost (6.5 mi / 10.5 km)
  • Seven Bridges Golf Club (7.7 mi / 12.5 km)
  • Arrowhead Golf Club (8.5 mi / 13.7 km)
  • Cantigny Golf Club (9.4 mi / 15.2 km)
  • The Dome at the Parkway Bank Sports Complex (10.1 mi / 16.3 km)

Exploring the natural landscape of Oakbrook Terrace

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Oakbrook Terrace is a great spot to appreciate mother nature. Here are some of the area’s most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Morton Arboretum (4.7 mi / 7.6 km)
  • Willowbrook Community Park (7.2 mi / 11.6 km)
  • Oak Park Conservatory (9.5 mi / 15.2 km)
  • Riverwalk Park (11.1 mi / 17.8 km)
  • Centennial Beach (11.1 mi / 17.9 km)
  • Spring Valley (12.7 mi / 20.5 km)

Travelling to and around Oakbrook Terrace

The nearest airport is in Chicago O'Hare International Airport (ORD), located 9.2 mi (14.8 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Chicago Midway Airport (MDW), which is 12.7 mi (20.5 km) away.

Frequently asked questions

What is the best area to stay in Oakbrook Terrace when booking a holiday rental?
When considering a holiday rental in Oakbrook Terrace, a fantastic area to consider is the vicinity around Oakbrook Centre. This neighbourhood is known for its vibrant setting and is home to one of the premier shopping destinations in the region, offering a variety of high-end shops and dining options. Visitors can enjoy a pleasant day exploring the centre, which features lush landscaping and a delightful selection of boutiques and eateries.Another appealing option is the area near the Drury Lane Theatre, which not only provides entertainment through its productions but also offers a lovely setting for a leisurely stroll. The theatre is a well-known cultural landmark in Oakbrook Terrace, attracting visitors with its diverse range of performances.In terms of accommodation, Oakbrook Terrace boasts a healthy selection of properties, ranging from modern apartments to charming townhouses, suiting various tastes and budgets.
When is the best time to visit Oakbrook Terrace for a holiday rental?
The best time to visit Oakbrook Terrace for a holiday rental is during the spring months from March to May. This period showcases the area's vibrant blooming gardens and comfortable temperatures, typically ranging from 5 to 20 degrees Celsius, making it ideal for outdoor activities and sightseeing. As the weather warms up, visitors can explore nearby attractions such as the beautiful Oakbrook Centre for shopping and dining, or enjoy leisurely strolls in the local parks.July marks the peak tourist season, attracting many visitors who are eager to enjoy summer events and festivals. During this lively month, the atmosphere is vibrant and full of energy, great for those who thrive in sociable environments. However, if you're looking for a more tranquil experience, consider visiting in December when the holiday spirit infuses the area with festive cheer, and you can enjoy seasonal decorations throughout the town.For those who appreciate a good deal, the shoulder months of late autumn, particularly October, offer a chance to enjoy the stunning fall colours while avoiding the crowds. This time is great for those who value comfort and convenience, as you can explore the area at a more leisurely pace.
What are the top attractions in Oakbrook Terrace?
In Oakbrook Terrace, visitors can enjoy a range of attractions and activities. The Oakbrook Centre is a premier shopping destination featuring a variety of upscale shops and dining options, making it a popular spot for both locals and tourists. Additionally, the area is home to the Drury Lane Theatre, which offers a diverse lineup of performances, including musicals and plays, providing a cultural experience for theatre enthusiasts.For those who appreciate nature, the nearby York Woods County Forest Preserve offers beautiful walking trails and picnic areas, great for a leisurely day outdoors. Additionally, the Oakbrook Terrace Park District boasts several parks and recreational facilities, allowing visitors to engage in sports or simply relax in green spaces.
Are all fees included in the Oakbrook Terrace 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 Oakbrook Terrace holiday homes with parking?
Stayz offers a wide selection of holiday homes in Oakbrook Terrace 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 Oakbrook Terrace holiday homes?
You can find great discounts on holiday homes in Oakbrook Terrace 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 Oakbrook Terrace holiday home booking on Stayz?
To find Oakbrook Terrace 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 Oakbrook Terrace?
A long-stay holiday home in Oakbrook Terrace 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 Oakbrook Terrace holiday home?
Book your Oakbrook Terrace 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 Oakbrook Terrace?
Prices for holiday homes in Oakbrook Terrace 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 Oakbrook Terrace 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.

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