Oak Brook holiday rentals

We found 597 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Oak Brook that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday homes have the best amenities for spending time at your holiday home, which might include Wi-Fi and a hot tub. Whatever you're looking for, you're sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Oak Brook

Showing deals for:22 Jan - 29 Jan

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

5 bedrooms/ 3 bathrooms/2 living rooms Elegant Escape at Burr Ridge/ La Grange

Burr Ridge

8% off
AU$5,556
for 7 nights, 1 home
AU$794 per night
includes taxes & fees
5 bedrooms/ 3 bathrooms/2 living rooms Elegant Escape at Burr Ridge/ La Grange
Room
Dining
Living area
Private kitchen
Exceptional
(11 reviews)

Quick Access to O'Hare and Chicago downtown

Melrose Park

8% off
AU$3,486
for 7 nights, 1 home
AU$498 per night
includes taxes & fees
Quick Access to O'Hare and Chicago downtown
Private kitchen
Exterior
Interior
Outdoor dining
Exceptional
(27 reviews)

Beautiful Berwyn Bungalow Close to Downtown Chicago

Berwyn

8% off
AU$3,467
for 7 nights, 1 home
AU$495 per night
includes taxes & fees
Beautiful Berwyn Bungalow Close to Downtown Chicago
Room
Property grounds
Living area
Terrace/patio
Exceptional
(9 reviews)

Rare Historic One Bedroom Carriage House in Downtown Glen Ellyn

Glen Ellyn

8% off
AU$2,354
for 7 nights, 1 room
AU$336 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
Master bedroom w/king size memory foam bed
Open concept kitchen
Exceptional
(25 reviews)

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

Wood Dale

12% off
AU$4,145
for 7 nights, 1 home
AU$592 per night
includes taxes & fees
Wonderful in Wood Dale, right by O’Hare airport!
Front Porch
Dining Room
Dining Room
Bedroom 1, Queen, Upstairs
Exceptional
(18 reviews)

Steps to Shops, Restaurants, Trains; 5BR, 14 Guests, Parking

Forest Park

28% off
AU$4,379
for 7 nights, 1 home
AU$626 per night
includes taxes & fees
Steps to Shops, Restaurants, Trains; 5BR, 14 Guests, Parking
Living area
Interior
Dining
Living area
Exceptional
(25 reviews)

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

Berwyn

8% off
AU$1,505
for 7 nights, 1 apartment
AU$215 per night
includes taxes & fees
Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT
Living area
Interior
Dining
Private kitchen
Wonderful
(43 reviews)

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

Berwyn

8% off
AU$1,883
for 7 nights, 1 apartment
AU$269 per night
includes taxes & fees
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
Room
Dining
Living area
Living area
Wonderful
(22 reviews)

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

Berwyn

8% off
AU$1,578
for 7 nights, 1 apartment
AU$225 per night
includes taxes & fees
Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI
Living area
Dining
Living area
Private kitchen
Exceptional
(8 reviews)

Modern 4-bedroom house in peaceful Westmont area

Westmont

8% off
AU$4,586
for 7 nights, 1 home
AU$655 per night
includes taxes & fees
Modern 4-bedroom house in peaceful Westmont area
Terrace/patio
Private kitchen
Interior
Living area
Wonderful
(17 reviews)

French Country Cottage in lovely Glen Ellyn!

Glen Ellyn

8% off
AU$7,211
for 7 nights, 1 home
AU$1,030 per night
includes taxes & fees
French Country Cottage in lovely Glen Ellyn!
Private kitchen
Living area
Room
Dining
Exceptional
(23 reviews)

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

Berwyn

8% off
AU$1,545
for 7 nights, 1 apartment
AU$221 per night
includes taxes & fees
Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
Dining
Living area
Room
Interior
Very good
(5 reviews)

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

Berwyn

8% off
AU$1,619
for 7 nights, 1 apartment
AU$231 per night
includes taxes & fees
Chicago style apt/Near Hosp/ORD/MDW/DT
Magnificent tunes
Night View
A Viking Stove and Quartz Countertops, You decide whats cooking.
The side view
Exceptional
(26 reviews)

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

Oak Park

11% off
AU$1,982
for 7 nights, 1 apartment
AU$283 per night
includes taxes & fees
First floor of Historic Oak Park Villa, Grge:2Cars
Interior
Private kitchen
Room
Dining
Exceptional
(12 reviews)

Prime Location - Cozy Naperville HomeStay - GameRoom

Naperville

8% off
AU$2,865
for 7 nights, 1 home
AU$409 per night
includes taxes & fees
Prime Location - Cozy Naperville HomeStay - GameRoom
Marathoners love staying with us for obvious reasons. Jogging comes naturally in this environment.
Interior
The building was constructed by German carpenters brought in by the Kettlestrings family more than a 125 years ago.
Putting pool is fun for both adults and kids.
Exceptional
(24 reviews)

Top floor of Historic Oak Park Home /2 Car Garage

Oak Park

11% off
AU$1,964
for 7 nights, 1 apartment
AU$281 per night
includes taxes & fees
Top floor of Historic Oak Park Home /2 Car Garage
Dining
Private kitchen
Interior
Exterior detail
Exceptional
(16 reviews)

Large Renovated 1st FL Suite Forest Park/Oak Park

Forest Park

11% off
AU$1,984
for 7 nights, 1 apartment
AU$283 per night
includes taxes & fees
Large Renovated 1st FL Suite Forest Park/Oak Park
Dining
Living area
Private kitchen
Interior detail
Exceptional
(14 reviews)

Ridgeland Retreat/ Street level Apt easy access

Berwyn

8% off
AU$2,200
for 7 nights, 1 apartment
AU$314 per night
includes taxes & fees
Ridgeland Retreat/ Street level Apt easy access
Dining
Room
Living area
Bathroom
Exceptional
(15 reviews)

Chic & Cozy near ORD>MDW>DT>HOSP

Berwyn

8% off
AU$1,874
for 7 nights, 1 apartment
AU$268 per night
includes taxes & fees
Chic & Cozy near ORD>MDW>DT>HOSP
Living area
Dining
Dining
Interior
Exceptional
(35 reviews)

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

Berwyn

8% off
AU$1,633
for 7 nights, 1 apartment
AU$233 per night
includes taxes & fees
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
Private kitchen
Living area
Room
Miscellaneous
Exceptional
(8 reviews)

Cozy 2-bedroom 15 min to downtown Chicago

Cicero

8% off
AU$2,029
for 7 nights, 1 apartment
AU$290 per night
includes taxes & fees
Cozy 2-bedroom 15 min to downtown Chicago
Private kitchen
Dining
Living area
Property grounds
Exceptional
(41 reviews)

Clean and Comfy Updated Apt in Convenient Location

Forest Park

8% off
AU$1,822
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 lush setting of Oak Brook is ready to explore

The area's entertainment and culture are just some of the reasons to come on holiday to Oak Brook. Travellers to this welcoming city praise the shopping, restaurants and forests. Wrigley Field and McCormick Place 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 and around Oak Brook

Are you hoping to discover top things to see and do while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Oak Brook a fun place to get away to. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Oak Brook Golf Course (1.3 mi / 2 km)
  • Galloping Ghost (5.3 mi / 8.5 km)
  • Cantigny Golf Club (10.4 mi / 16.7 km)
  • The Dome at the Parkway Bank Sports Complex (10.6 mi / 17 km)
  • Cog Hill Golf & Country Club (11.6 mi / 18.6 km)
  • LEGOLAND® Discovery Center (14.4 mi / 23.2 km)

Exploring the natural features in Oak Brook

Whether you're an adventurous traveller or just want to spend some time taking in the scenery, Oak Brook is a great place to spend some time outside. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Millennium Park (17.3 mi / 27.8 km)
  • Grant Park (17.3 mi / 27.8 km)
  • Morton Arboretum (5.2 mi / 8.3 km)
  • Willowbrook Community Park (6.1 mi / 9.9 km)
  • Riverwalk Park (11.5 mi / 18.5 km)
  • Centennial Beach (11.5 mi / 18.5 km)

Travelling to and around Oak Brook

The nearest airport is in Chicago O'Hare International Airport (ORD), located 9.8 mi (15.8 km) from the city centre. If you can't find a flight that's convenient for your trip, you could book a flight to Chicago Midway Airport (MDW), which is 11.5 mi (18.5 km) away.

Frequently asked questions

What is the best area to stay in Oak Brook when booking a holiday rental?
When considering a holiday rental in Oak Brook, Illinois, the best area to stay is near the Oak Brook Centre. This upscale shopping destination offers a delightful array of stores, dining options, and a pleasant atmosphere for leisurely strolls. The nearby area features a variety of properties, suiting different preferences and budgets, from luxurious options to more modest accommodations.Another charming neighbourhood to consider is the region surrounding the Drury Lane Theatre. This area not only provides convenient access to high-quality productions but also boasts a selection of restaurants and parks, superb for relaxing after a day of exploration. The green spaces in Oak Brook, such as York Woods County Forest Preserve, offer beautiful trails and picnic spots, making it an ideal choice for nature enthusiasts.
What is the most popular type of holiday rental accomodation in Oak Brook?
In Oak Brook, holiday houses are the most popular type of holiday rental, with several available throughout the area. These homes typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups. Many also include outdoor spaces such as gardens or patios, superb for enjoying the pleasant surroundings.
Are there any remote work holiday rentals in Oak Brook?
In Oak Brook, Illinois, there are several holiday rentals suitable for remote work. The area offers a variety of accommodations equipped with essential amenities that cater to those working from home. Many properties feature reliable internet services, allowing for smooth connectivity, and often include comfortable workspaces, such as desks or dedicated office areas.Oak Brook is known for its pleasant suburban atmosphere, complete with parks and green spaces, providing a refreshing environment for breaks from work. Additionally, the area is conveniently located near shopping centres and restaurants, making it easy for travellers to unwind after a productive day. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Oak Brook?
In Oak Brook, popular holiday rental amenities include fireplaces, fitness facilities, onsite parking, and WiFi. Many properties offer these features to ensure a comfortable stay, with fireplaces providing a cosy atmosphere during colder months. Fitness facilities cater to those looking to maintain their routines while travelling, and onsite parking is a convenient option for guests with vehicles. WiFi is typically available across rentals, allowing visitors to stay connected.
When is the best time to visit Oak Brook for a holiday rental?
The peak season for visiting Oak Brook falls between May and July, with July being the most popular month for holiday rentals. This vibrant period is superb for travellers seeking a mix of outdoor adventures and cultural experiences, as the weather is warm, and various local events and festivals are in full swing.During these months, you can enjoy pleasant temperatures ranging from 20 to 30 degrees Celsius, ideal for exploring the picturesque parks and gardens that Oak Brook has to offer. Outdoor enthusiasts will appreciate the numerous walking and biking trails, while families can take advantage of the nearby attractions, such as the Brookfield Zoo and Oakbrook Centre, a premier shopping destination.If you're looking for a more budget-friendly experience, consider planning your visit in October. This month features a lovely autumn atmosphere with cooler temperatures and stunning fall foliage, making it a great time for scenic walks and enjoying the local parks without the hustle and bustle of peak season.Ultimately, the best time to book a holiday rental in Oak Brook depends on whether you're after the lively summer activities or the more tranquil, picturesque autumn experiences.
What are the top attractions in Oak Brook?
In Oak Brook, visitors can enjoy a variety of attractions that cater to both nature lovers and shopping enthusiasts. The Oak Brook Centre is a premier shopping destination, featuring a wide range of high-end retailers and dining options surrounded by beautifully landscaped gardens. This outdoor mall offers a pleasant atmosphere for leisurely strolls and outdoor dining.For those interested in nature, the nearby Fullersburg Woods Nature Education Centre provides opportunities for hiking and wildlife observation. The scenic trails and serene surroundings make it a lovely spot for a day out in nature. Additionally, the Drury Lane Theatre offers a vibrant cultural experience, with a rotating schedule of live performances, including musicals and plays, making it a popular choice for entertainment in the area.Families can also enjoy the nearby York Woods County Forest Preserve, which features picnic areas and walking paths, providing a great setting for outdoor activities and relaxation.
Are all fees included in the Oak Brook 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 Oak Brook holiday homes with parking?
Stayz offers a wide selection of holiday homes in Oak Brook 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 Oak Brook holiday homes?
You can find great discounts on holiday homes in Oak Brook 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 Oak Brook holiday home booking on Stayz?
To find Oak Brook 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 Oak Brook?
A long-stay holiday home in Oak Brook 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 Oak Brook holiday home?
Book your Oak Brook 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 Oak Brook?
Prices for holiday homes in Oak Brook 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 Oak Brook 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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