
Holiday houses in Oakbrook Terrace
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Top-rated holiday rentals in Oakbrook Terrace
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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

Enchanted Garden Treehouse (Amenity*)
Summer's here, the treehouse air conditioned and cozy, and the hot/cool tub ready! Relax in our luxurious, 420 friendly, very private, 4' deep cedar hot tub nestled in the evergreens, while the moon and stars swirl overhead, the waterfall tumbles into the koi pond, and the fire table and torches blaze. The stream makes this a wildlife refuge, with many birds, squirrels, rabbit & fox. Come experience the magic and make a special memory! See why Chgo Magazine rates us top 3 staycations in Chgo!

Cozy 5BD Home with Scandinavian Vibes
✨ Newly Renovated Spacious Scandinavian-Style Home Near Chicago Airport ☀️ Enjoy your stay in this beautiful, fully equipped 5-bd, 2-bath home featuring modern Scandinavian-style furniture, rattan details, thoughtful touches, and all the comforts you need for a relaxing getaway. This spacious and inviting house is just a short drive from Chicago O’Hare Airport and downtown, offering both convenience and comfort yet it remains peaceful and quiet, so you won’t hear the noise of passing planes.

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.

A+: 4BR-3BTH Spacious Home w/ 2 Living Rooms
Welcome to your perfect home away from home! This spacious 4BR, 3BT home has been newly remodeled with a fresh, modern design and thoughtful finishes throughout. With plenty of room to spread out, it’s ideal for families, groups, or extended stays. Enjoy comfortable sleeping arrangements, updated bathrooms, a fully equipped kitchen you need for a relaxing and convenient stay. Whether you’re visiting for work or leisure, the home offers functionality to make your trip truly enjoyable.

Stylish 1970s Home for Vintage Getaway!
Embrace Timeless Charm: Step into the enchanting world of a meticulously restored 1971 Mid-Century gem. Located just 30 minutes from downtown Chicago in Glen Ellyn, this unique retreat captures the essence of the 1960s and 70s. Every corner showcases vintage artifacts, offering an unforgettable stay. Enjoy the spacious Great room, well-equipped kitchen, and outdoor patio. Lounge by the 70-inch TV, groove to vintage vinyl records, and relish classic board games for a nostalgic getaway.

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!

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!

Sunny Garden Unit Efficiency Studio in Wheaton
Enjoy a cozy getaway in our sunny basement studio, conveniently situated near downtown Wheaton, downtown Glen Ellyn, Wheaton College, College of Dupage, and trains to the big city. If you're driving, we're a few minutes from the highway, as well. The space is outfitted with a memory foam queen bed, fold-out sofa, workspace, a TV with a variety of streaming services, free Wifi and a kitchenette for easy meals and snacks. We look forward to hosting you!

Cozy Home in Brookfield
Discover tranquility just minutes from the busy city life! Nestled in the heart of Brookfield, IL, our charming home offers the perfect blend of suburban serenity and urban convenience. Just an 8-minute walk from the train station, you'll find easy access to downtown Chicago while enjoying the peaceful atmosphere of our neighborhood. Max 4 overnight guests. No parties or events. Pets allowed (no exotic pets or animals with a bite history).

“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!

Modern Boho house in Lombard 7 min to Metra
Kick back and relax in this calm, stylish space. Visiting family in Chicagoland area? Traveling for work? Lombard is centrally located 30 min to everywhere! The house is only 6 min to Oakbrook Shopping and Business Center and upscale shopping and fabulous restaurants like RH with rooftop restaurant, 8 min to Yorktown Shopping Center. Whatever your travel purpose is, we will be happy to host you! Welcome home!
Popular amenities for Oakbrook Terrace holiday rentals
Other great holiday rentals in Oakbrook Terrace

“The Warrenville Grove”

Comfort Haven

Modern 2BR Near O’Hare • Parking • Private Yard

New Home | O'Hare Airport

Private & quiet🌲 O'Hare 8mi✈️ D/T Chicago 22mi 🏙

RANCH, House-tel: updated full kitchen, comfy beds

Cute & Cozy Westmont, IL House Near the Best Areas

Homey Brookfield Gem — 4 Beds, 2 Baths, Great Yard
Frequently Asked Questions
What are the best places to stay in Oakbrook Terrace?
Neighborhoods around Oakbrook Terrace’s parks and shopping districts are often preferred for stays, offering convenient access to local attractions. There are also options near business and cultural centers.
What are the best things to do in Oakbrook Terrace with kids?
Kids can enjoy playgrounds in local parks, family-friendly performances at Drury Lane Theatre, and hands-on activities at nearby children’s museums. Community recreation centers also have programs for young visitors.
What are some of the best things to do in Oakbrook Terrace?
Explore Drury Lane Theatre for live shows, wander local parks, and shop or dine in vibrant centers. Seasonal festivals and community events add extra color to the city’s cultural calendar.
How is the weather in Oakbrook Terrace?
Oakbrook Terrace has cold winters ranging from 19–32°F (-7–0°C), and warm summers near 66–85°F (19–29°C), with spring and fall bringing moderate temperatures and occasional rain. Layered clothing is helpful year-round.
When is the best time to visit Oakbrook Terrace?
Late spring through early fall is often recommended, when temperatures are milder from 51–85°F (10–29°C) and outdoor events take place. Winter brings colder weather, making indoor activities a cozy option.
What are the best places to visit in Oakbrook Terrace?
The Drury Lane Theatre, local parks, and shopping centers are frequently suggested places to explore in Oakbrook Terrace. Depending on interests, visitors may also enjoy nearby art galleries and performance venues.
What are some hiking trails in Oakbrook Terrace?
Oakbrook Terrace has walking and jogging paths in local parks, with paved and natural sections for easy strolls. Nature reserves and forest preserves around the area present more scenic routes for hikers.
What are some family activities we can do in Oakbrook Terrace?
Families in Oakbrook Terrace can explore parks, take part in seasonal community events, and visit interactive art or science spaces nearby. Many find local playgrounds and recreation centers appealing for group fun.
What are some of the best day trip ideas from Oakbrook Terrace?
Day trips from Oakbrook Terrace often include exploring nearby botanical gardens, art museums, or vibrant urban neighborhoods. Visits to natural preserves and regional landmarks are frequently suggested.
Are there any pet friendly accommodations available in Oakbrook Terrace?
Many stays in Oakbrook Terrace welcome pets, especially in neighborhoods near green spaces and walking trails. Look for rental options that emphasize pet amenities or easy park access.
What are some local tips for visiting Oakbrook Terrace?
Check for community event schedules, explore nearby parks for quiet afternoons, and bring layers for weather changes. Locals often recommend catching a theater performance or sampling family-run restaurants.
What is Oakbrook Terrace known for?
Oakbrook Terrace is recognized for its blend of business centers, open green spaces, and accessible shopping districts. The city is also known for its community gatherings and theater performances.
What are the best hidden gems to explore in Oakbrook Terrace?
Locally rooted art galleries, small parks, and community theater spaces are often appreciated as hidden gems around Oakbrook Terrace. Consider visiting lesser-known eateries and neighborhood cafes for distinct experiences.
What are the best foods to try in Oakbrook Terrace?
Oakbrook Terrace has a mix of classic American fare, Italian dishes, and globally inspired menus at local restaurants. Deep-dish pizza, fresh salads, and hearty sandwiches are frequently suggested.
What should I bring for a trip to Oakbrook Terrace?
Pack comfortable walking shoes, versatile layers suited to temperatures from 19–85°F (-7–29°C), and a light rain jacket. If planning outdoor activities, sun protection and reusable water bottles make outings easier.
What is the nightlife in Oakbrook Terrace like?
Oakbrook Terrace has casual nightlife with relaxed bars, local eateries, and occasional live music. Around the area, visitors often find lounge venues and spots for after-dinner drinks.
What are the most popular events or festivals in Oakbrook Terrace?
Oakbrook Terrace has seasonal community festivals, summer concerts in the park, and frequent theater productions. Holiday events and outdoor markets are especially popular during late spring and summer.
Are there family friendly vacation rentals in Oakbrook Terrace?
Vacation rentals in Oakbrook Terrace include options suited for families, such as homes near parks or with multiple bedrooms and spacious living areas. Many neighborhood stays feature amenities tailored for children.
Destinations to explore
- Chicago Holiday rentals
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- St. Louis Holiday rentals
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- Detroit Holiday rentals
- Milwaukee Holiday rentals
- Traverse City Holiday rentals
- Des Moines Holiday rentals
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- 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
- University of Chicago
- Humboldt Park
- Guaranteed Rate Field
- Lincoln Park Zoo
- Loyola University Chicago
- Union Park
- Frank Lloyd Wright Home and Studio
- Donald E Stephens Convention Center
- Wilmot Mountain Ski Resort
- Garfield Park Conservatory
- Illinois Beach State Park





