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Holiday rentals in Oakbrook Terrace

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Top-rated holiday rentals in Oakbrook Terrace

Guests agree: these stays are highly rated for location, cleanliness and more.

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Superhost
A bright sleeping area features a spacious bed adorned with a floral-patterned coverlet. Natural light filters through the window, illuminating the wooden floors. A small desk and comfortable chair are positioned nearby, alongside a mirror reflecting the room's layout.
Flat in Hillside
4.86 out of 5 average rating, 192 reviews

Easy, Cool, safe place to stay.

Level 1 car charging available, message me. 17 mins Ohare airport 25 mins to downtown Chicago I want you to enjoy your stay, and I don't have rules other than basic ones like noise and guest limit. Have Fun Very safe and quiet 420 might be ok, please message me* 3 Queen-size beds. One is self-iflating inside the middle closet. Well stocked kitchen 2 Private parking lot spaces. Kreuger coffee 2 tvs Netflix There is no smoking in the unit or inside building* Coin laundry is available

Superhost
A cozy living room features a brick fireplace as a focal point, surrounded by comfortable leather seating arranged for relaxation. Light-colored curtains frame large windows, while a plush area rug adds warmth to the wooden floor. A wooden door and wall decor complement the inviting space.
Home in Glen Ellyn
4.89 out of 5 average rating, 216 reviews

Home in Glen Ellyn

Beautiful 5 bedroom, 2.5 bath home in Glen Ellyn, fully furnished with everything you may need for a wonderful stay! Located in the peaceful suburbs of Glen Ellyn, the area is perfect for families or friends who would like a comfortable getaway. Located 40 minutes from downtown Chicago and Midway airport and 30 minutes from O'Hare airport. Located nearby major highways and shopping centers. Large, private and completely enclosed backyard perfect for kids to play in or a relaxed evening of BBQ!

Guest favourite
A spacious artist loft features a living area with hardwood floors and large windows allowing natural light. A leather sofa is positioned in the center, with stylish chairs nearby. The open kitchen is visible in the background, along with a modern dining space under soft lighting.
Loft in Brookfield
4.88 out of 5 average rating, 179 reviews

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

Guest favourite
Home in Villa Park
4.9 out of 5 average rating, 42 reviews

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.

Top guest favourite
A spacious living room features a large sectional sofa adorned with various cushions, complemented by a cozy throw. A sleek flat-screen television is mounted above a natural stone fireplace. Large windows allow natural light to fill the room, enhancing the inviting atmosphere.
Home in Lombard
4.96 out of 5 average rating, 57 reviews

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.

Top guest favourite
A living area showcases a wooden entertainment center with a TV, flanked by a decorative console table and two lamps. The space features hardwood floors and a neutral color palette, complemented by a circular wall mirror. A staircase in the background leads to the upper level.
Apartment in Clarendon Hills
5 out of 5 average rating, 129 reviews

Apartment in Clarendon Hills.

Newly renovated Suite in multi family home in Clarendon Hills. Main level: fully equipped kitchen/island, dining area, living room & family room with fireplace. Upper level: Bedroom 1 - king size bed, walk in closet​, private bathroom/shower.​ Bedroom 2 - queen bed​, closet.​ Bedroom 3 - size bed​, closet. Living room has a pull-out sofa bed​. Family room with gas fireplace, access to deck/outdoor area.​ Easy access to restaurants, shopping (Oak Brook Mall minutes away), Metra, O’Hare.

Superhost
Home in Elmhurst
4.7 out of 5 average rating, 20 reviews

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.

Top guest favourite
Home in Glen Ellyn
5 out of 5 average rating, 57 reviews

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.

Superhost
A spacious living area features an array of seating options, including a light gray sofa and colorful accent chairs. Natural light floods in through multiple windows, highlighting the wood flooring and inviting decor. A dining table is situated nearby, along with a small coffee station.
Home in Elmhurst
4.77 out of 5 average rating, 150 reviews

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!

Top guest favourite
A spacious screened-in porch features comfortable seating arrangements, including a sectional sofa and a dining table. A hammock is hung in the corner, providing a relaxed space. Natural light floods in, highlighting views of the surrounding trees and yard, creating a refreshing retreat.
Home in Addison
4.99 out of 5 average rating, 91 reviews

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

Must agree to all house rules prior to booking (see below under "Other details") Get your zen at this one-of-a-kind private home. Situated on a serene lot adjacent to the forest preserve; steps to the splendid walking path/fishing pond. Feels like a hidden gem in the woods, yet with the convenience of easy access to Rt. 83, Irving Park, I-290, O'Hare (minus the overhead noise), golf, shopping, restaurants, and Metra. Enjoy this peaceful oasis- truly a home away from home!

Guest favourite
The exterior of the vintage garage apartment is shown, featuring a bright yellow facade with two white garage doors. A large window is positioned above the doors, with greenery surrounding the property, contributing to the charming appearance.
Guest house in Villa Park
4.92 out of 5 average rating, 159 reviews

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!

Top guest favourite
A single-story brick home with a well-maintained front yard features green shrubs and a neat pathway leading to the entrance. Large windows allow natural light to illuminate the interior, while a tree provides shade near the entrance.
Home in Brookfield
4.99 out of 5 average rating, 100 reviews

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).

Popular amenities for Oakbrook Terrace holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Oakbrook Terrace

Guest favourite
A well-lit dining area features a rectangular table accompanied by four wooden chairs and a bench. Natural light filters through large windows, illuminating the space. A small potted plant is centered on the table, enhancing the clean and modern decor.
Home in Westmont
4.89 out of 5 average rating, 57 reviews

Cute & Cozy Westmont, IL House Near the Best Areas

Guest favourite
A modern kitchen features a large farmhouse sink with a sleek faucet, set against a tiled backsplash. Natural light enters through a window above the sink, illuminating wooden countertops while a decorative rug with a floral design lies on the floor.
Home in Villa Park
4.9 out of 5 average rating, 49 reviews

Comfort Haven

Top guest favourite
A cozy living room is furnished with multiple seating options, including wicker chairs and a plush couch decorated with assorted cushions. A round coffee table sits at the center, accompanied by a basket and a small side table. A softly glowing lamp provides warm light, and an electric fireplace is positioned against the wall.
Guest suite in Wheaton
5 out of 5 average rating, 63 reviews

The Garden Flat

Superhost
A cozy living area is highlighted by a wood-burning fireplace, where a warm fire flickers. A sleek coffee table sits in front of a comfortable sectional sofa, complemented by a textured area rug. Two glasses of wine rest atop the table, adding a touch of relaxation.
Apartment in Lombard
4.81 out of 5 average rating, 70 reviews

Smoke & Pet Free, Washer Dryer, Fireplace, Balcony

Guest favourite
Home in Naperville
5 out of 5 average rating, 9 reviews

Elegant 4BR Tudor Retreat — Spacious, Peaceful!

Top guest favourite
A cozy living area features a modern brown sofa with light accent pillows, a circular coffee table, and a small dining table for two. Natural light enters through a curtain-covered window, highlighting simple wall art and greenery. The space is enhanced by warm wood flooring.
Guest suite in Wheaton
4.98 out of 5 average rating, 61 reviews

Sunny Garden Unit Efficiency Studio in Wheaton

Top guest favourite
A modern kitchen features sleek dark cabinetry paired with light wood finishes. Stainless steel appliances include a refrigerator, oven, and microwave. A spacious countertop offers ample prep space, and a window allows for natural light to brighten the area.
Home in Schaumburg
4.99 out of 5 average rating, 76 reviews

Suburban Fab

Guest favourite
A cozy living area features a white sofa paired with a light-colored armchair. A wooden coffee table sits centrally, while bookshelves filled with books and decor items occupy one side. Natural light enters through multiple windows dressed in soft curtains, creating a warm atmosphere.
Home in Wood Dale
4.95 out of 5 average rating, 58 reviews

Cozy 2 bedroom home in a wonderful neighborhood.

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