
Holiday rentals in Oak Brook
Find and book unique accommodation on Airbnb
Quick stats about holiday rentals in Oak Brook

Total holiday rentals
Explore 20 holiday rentals in Oak Brook

Nightly prices starting at
Oak Brook holiday rentals start at £45 per night before taxes and fees

Verified guest reviews
Over 1,140 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Oak Brook holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Oak Brook rentals

4.8 Average rating
Oak Brook stays are highly rated by guests – averaging 4.8 out of 5!
Top-rated holiday rentals in Oak Brook
Guests agree: these stays are highly rated for location, cleanliness and more.

Charming Riverfront Stay | Heart of Downtown
Welcome to The Riverfronts! Three boutique hotel rooms perfectly situated along the river in downtown West Dundee, offering scenic views and modern comforts. ✔ Riverfront Location: Enjoy the scenic riverwalk just steps away. ✔ Prime Downtown Spot: In the heart of downtown Dundee, minutes from top attractions and dining. ✔ Exclusive Group Booking: Reserve just one or all three units for your entire party. ✔ Outdoor Firepit: Unwind by the firepit, perfect for evening gatherings. ✔ Sleeps 4: Each

1920s fully updated unique open artist loft space
True artist living loft space!!! One of a kind space in a safe area of the western suburbs close to the city and easy commute to shops stores. very close to trains buses and expressways. Private parking lot. No unit above or below. Quiet and private spacious updated wide open loft. Hardwood floors throughout forced heat and ac slated steel designer bathroom.. Double oven dishwasher electric cooktop sub zero fridge microwave and toaster oven. Ceiling fans two beds. Can sleep 6 for added cost

Luxurious apartment in great central location!
Welcome to the Troost House. This property is newly remodeled with high end finishes including Quartz counters, hardwood floors and fully equipped with brand-new stainless appliances. This 2BR 1B offers its own laundry room as well as a 1 car garage parking space. Superb location with easy access to major highways, a 5-minute walk to Blue line train station, a 3-minute drive to Loyola Medical Center, a 10-minute drive to DT Chicago, and near the heart of DT Forest Park and historic Oak park.

Spacious Home in Chicago Suburbs
Enjoy your stay in Chicagoland in this gorgeous, newly updated home. After a full day of sightseeing in the Windy City or hitting the local shops and attractions, this is a restful homebase to return to. The spacious fenced-in backyard and patio, a comfortable and tastefully furnished basement, and the full kitchen with amenities provide the perfect environment to unwind. You’ll find plenty of seating, sleeping accommodations for nearly a dozen, and an open layout that fosters connection.

Couples retreat Duplex- Side B. In law suite 1/1
Wake up to the amazing view of lake. Small apt with private entrance attached to main house that is also rented. There is a hot plate and a large counter top oven. A deep kitchen sink, med size fridge, and microwave. Living area is two chairs. There is a private deck with a beautiful view of the lake. The yard and driveway are shared. There is potential to hear people next door. Currently no control over heat or AC. We keep at reasonable temp 68-75 and give a separate heater and fan.

Penthouse In The Historic Hobbs
Experience luxury and historic charm at the Penthouse in the Historic Hobbs. Built in 1892, and restored in 2023, this new one bedroom corner unit offers a panoramic view of the Aurora skyline. Cook a delicious meal in the fully stocked kitchen. Dine at the bespoke table in the window bay under the iconic onion dome. Relax on the cozy sofa and enjoy a movie on the big screen TV. Rest in the plush king-sized bed. This urban retreat is near coffee, shopping, art and entertainment.

Cozy Ranch w/ King Bed & 3 Baths – Great Location!
Feel at home at this cozy split-level ranch with separate spaces perfect for relaxing—whether you’re staying with family or traveling for work. Watch your favorite show in the basement while someone else is peacefully reading a book on the main level or taking a nap upstairs. Located on a quiet, dead-end street, but just 22 mins from O’Hare Airport, minutes from I-290 and 83rd, and 10 minutes from Oak Brook Mall. Our excellent guest-to-bathroom ratio ensures comfort for everyone!

Smoke & Pet Free, Washer Dryer, Fireplace, Balcony
Welcome to our cozy retreat! Fully furnished for affordability and convenience, our prime location near Downers Grove, Wheaton, Oakbrook, and Downtown Chicago ensures the perfect base for your stay. Enjoy free parking, washer-dryer, dishwasher, and amenities like linens, dishes, cookware, cable, wireless internet, queen-size beds, smart TV, and Hulu access. Little touches make guests feel truly at home, creating a delightful and memorable stay, whether for business or leisure.

Charming Home in Westmont, Close to Chicago!
Very peaceful neighborhood! This house has the best location in the Western Suburbs of Chicago. Walking distance to downtown Westmont and train station. A few minutes drive to malls, parks and everything...eight minutes drive to downtown Downers Grove. 30 minutes drive to downtown Chicago. This house has an appealing open floor plan and a well equipped kitchen. Each bedroom has its own TV. Lower level game room has the most popular board games, toys and an air hockey table.

Eclectic Coach House Apartment
Vintage Charmer! 1935 Sears Craftsman Coach House garage apartment. Beautiful safe neighborhood surrounded by historic homes and just steps from the Illinois prairie path, parks, brewery's/bars, restaurants and more! With an eclectic boho chic vibe, featuring full kitchen and on site private washer/dryer. Overlooking an accessible lovely backyard! Close to airports and easy access to public transportation/major highways. Just 30 min from the Chicago Loop!

“The Warrenville Grove”
This bright 2-bedroom home is designed for comfort, with a modern living space, fully equipped kitchen, washer & dryer and a cozy yard to unwind in. Perfect for small groups or families, you’ll be close to local dining, parks, and just a short drive from Naperville and downtown Chicago. We are less than a mile away from the expressway I-88. Whether you’re here for work or leisure, this spot makes it easy to relax, recharge, and explore.

“The remote retreat”
We have a cozy one bedroom apartment that is available on the top floor of the home and has its own independent and separate entrance! Comes with free parking on premises; recently renovated; neighborhood is safe and quiet. Shopping center with grocery store, laundry mat and restaurant is available within walking distance! We are only 5 minutes from the expressway I-88 and 10 minutes from Naperville and the outlet mall in Aurora!
Popular amenities for Oak Brook holiday rentals
Other great holiday rentals in Oak Brook

Newly renovated Apartment.

Harmony Haven - 2 Parking Spaces!, Sleeps 4!

Comfort Haven

Stylish 1BR | A+ Location, Parking, Laundry

A+: 4BR-3BTH Spacious Home w/ 2 Living Rooms

2 Bedroom Apartment in La Grange

Big house in the BEST Location!

Stylish 1970s Home for Vintage Getaway!
When is the best time to visit Oak Brook?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £137 | £134 | £168 | £126 | £149 | £176 | £184 | £202 | £149 | £154 | £179 | £164 |
| Avg. temp | -4°C | -2°C | 4°C | 10°C | 16°C | 21°C | 24°C | 23°C | 19°C | 12°C | 5°C | -1°C |
Frequently Asked Questions
What are the best places to stay in Oak Brook?
Accommodations in Oak Brook include homes near shopping centers, tree-lined neighborhoods, or areas close to parks. Family-friendly rentals and suites are commonly available around Oakbrook Center.
What are the best things to do in Oak Brook with kids?
Children often enjoy hands-on experiences at Fullersburg Woods Nature Center, playful afternoons at local parks, and browsing shops or sweet treats at Oakbrook Center. Family-friendly events and mini-golf are frequently suggested.
What are some of the best things to do in Oak Brook?
Explore luxury shops and restaurants at Oakbrook Center, walk the scenic trails at Fullersburg Woods Nature Center, or visit the historic Mayslake Peabody Estate. Outdoor golf and family activities are frequently suggested.
How is the weather in Oak Brook?
Oak Brook has cold winters near 19–32°F (-7–0°C), warming to mild springs and summers around 51–85°F (10–29°C). Rain is more frequent in the spring, so packing for wetter months is helpful.
When is the best time to visit Oak Brook?
Late spring through early fall is often recommended for outdoor activities and milder temperatures around 50–80°F (10–27°C). Seasonal festivals and art shows add vibrant experiences during these months.
What are the best places to visit in Oak Brook?
Explore the Oakbrook Center for shopping and dining, stroll the paths at Fullersburg Woods Nature Center, or visit the Mayslake Peabody Estate. The area also has parks and golf courses for outdoor activities.
What are some hiking trails in Oak Brook?
Fullersburg Woods Nature Center has scenic trails winding through woodlands and along waterways. Mayslake Peabody Estate features quieter paths, and local parks offer walking and jogging routes for all ages.
What are some family activities we can do in Oak Brook?
Families often explore Oakbrook Center, hike at Fullersburg Woods Nature Center, or visit local playgrounds and golf courses. Seasonal outdoor events and art programs are also popular with kids and adults.
What are some of the best day trip ideas from Oak Brook?
Day trips from Oak Brook can include exploring nearby botanical gardens, visiting museums in surrounding cities, or discovering historic neighborhoods and lakefront parks. Seasonal outdoor festivals are also frequently suggested.
Are there any pet friendly accommodations available in Oak Brook?
Many accommodations in Oak Brook welcome pets, making it easy to bring furry friends along for your stay. Green spaces around the area encourage walks and pet-friendly outings.
What are some local tips for visiting Oak Brook?
Locals suggest arriving early for weekend shopping or special events and exploring nature trails for a quiet escape. Try locally owned restaurants for distinct flavors, and check for outdoor concerts during warmer months.
What is Oak Brook known for?
Oak Brook is known for its upscale shopping at Oakbrook Center, expansive parks, and corporate offices. The community has well-maintained green spaces and historic sites, often drawing families and business travelers.
What are the best hidden gems to explore in Oak Brook?
Discover tranquil trails in Fullersburg Woods, quiet garden spots at Mayslake Peabody Estate, or locally owned cafes tucked around Oakbrook Center. Small art galleries and historical sites often surprise visitors with unique stories.
What are the best foods to try in Oak Brook?
Oak Brook is known for American classics, Italian fare, and contemporary cuisines often found in local restaurants. Families frequently enjoy hearty burgers, wood-fired pizzas, and seasonal salads.
What should I bring for a trip to Oak Brook?
Pack comfortable clothing, a light jacket for cooler evenings, and a raincoat during wetter months. Shoes suitable for walking around shopping centers or nature trails are frequently recommended.
What is the nightlife in Oak Brook like?
Nightlife in Oak Brook centers around laid-back lounges, lively bars, and late-night dining in and near Oakbrook Center. Those seeking entertainment can enjoy live music or gatherings in casual venues.
What are the most popular events or festivals in Oak Brook?
Oak Brook has annual art fairs, local food festivals, and outdoor summer concerts that are often recommended. Seasonal celebrations and community gatherings around public spaces bring residents and visitors together throughout the year.
Are there family friendly vacation rentals in Oak Brook?
Oak Brook has vacation rentals suitable for families, with spacious layouts and amenities like kitchens and multiple bedrooms. The area is known for parks and shopping centers that families often enjoy together.
Destinations to explore
- Chicago Holiday rentals
- Indianapolis Holiday rentals
- Columbus Holiday rentals
- St. Louis Holiday rentals
- Louisville Holiday rentals
- Cincinnati Holiday rentals
- Detroit Holiday rentals
- Milwaukee Holiday rentals
- Traverse City Holiday rentals
- Des Moines Holiday rentals
- Downtown Chicago Holiday rentals
- Ann Arbor Holiday rentals
- Wrigley Field
- Soldier Field
- Lincoln Park
- United Center
- Grant Park
- Navy Pier
- Millennium Park
- Indiana Dunes State Park
- Naval Station Great Lakes
- 875 North Michigan Avenue
- Six Flags Great America
- The Field Museum
- Shedd Aquarium
- Chicago River Walk
- Humboldt Park
- University of Chicago
- Guaranteed Rate Field
- Lincoln Park Zoo
- Loyola University Chicago
- Frank Lloyd Wright Home and Studio
- Union Park
- Donald E Stephens Convention Center
- Wilmot Mountain Ski Resort
- Garfield Park Conservatory





