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Holiday houses 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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Guest favourite
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.
Apartment in Hillside

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

4.86 out of 5 average rating, 199 reviews
Guest favourite
A spacious living area features a large sectional sofa arranged around a circular coffee table. A television is positioned on a media stand, and natural light enhances the room through a large arched window, complemented by decorative plants and neutral-colored accents.
Home in Elmhurst

Premier 5BR/3BA Modern Retreat with King Suite!

Beautiful 5BR/3BA Retreat in a Chicagoland suburb! ☆ Newly renovated and stylish, this ultra spacious home features a modern open layout, luxurious bedrooms for everyone, a gourmet kitchen, and elegant bathrooms. Explore the Chicagoland with local shops and parks, then come home to relax in peace. Conveniently located in a prime area, a quick drive from the airport, train station, or downtown. Ideal for families, groups, or anyone seeking a clean comfortable home. Book now for a memorable stay.

4.96 out of 5 average rating, 77 reviews
Guest favourite
Home in Villa Park

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.

4.91 out of 5 average rating, 46 reviews
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

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.

4.97 out of 5 average rating, 61 reviews
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.
Condo in Clarendon Hills

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.

5.0 out of 5 average rating, 138 reviews
Superhost
Home in Elmhurst

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.

4.61 out of 5 average rating, 28 reviews
Guest favourite
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

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!

4.78 out of 5 average rating, 160 reviews
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.
Guesthouse in Villa Park

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!

4.93 out of 5 average rating, 165 reviews
Top Guest favourite
Apartment in Lombard

Spacious 3BR | Sleeps 8 Near Everything

Spacious, comfortable 3-bedroom apartment ideal for weekly & monthly stays. Fully equipped kitchen, brand-new beds & bedding, fast Wi-Fi, and a quiet residential setting—perfect for families, work travel, or extended visits. Just 30 minutes from Chicago with easy expressway access. Enjoy on-site laundry, a cozy living room, full dining area, and a small patio with fire pit. PARKING: 2 off-street parking spaces are included w/ the apartment.

5.0 out of 5 average rating, 36 reviews
Top Guest favourite
Home in Lombard

Home in Lombard

Relax at this peaceful, updated split-level home with 4 bedrooms and 3 baths. Main level features a modern kitchen, living and dining room, primary ensuite with a king bed, and two queen bedrooms. The lower level includes a family room, bedroom with two queen beds that sleep four. Enjoy a large backyard with double patios and fire pit. Close to I-355, shopping, restaurants, parks, and 30 minutes to downtown Chicago.

5.0 out of 5 average rating, 18 reviews
Top Guest favourite
A welcoming living room is highlighted by a comfortable sectional sofa with decorative pillows. A patterned area rug covers the hardwood floor, and a reading nook features a unique egg chair. Artwork adorns the walls, complemented by greenery from potted plants.
Home in Lombard

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!

4.99 out of 5 average rating, 161 reviews
Guest favourite
A two-story home is showcased with a mix of wood and white brick siding. The front yard contains a stone border with greenery. A driveway leads to a two-car garage, and a decorative lantern stands near the entrance. Large windows allow natural light into the living spaces.
Home in Villa Park

Executive retreat in Villa Park

Our 4BR/3BA executive home in Villa Park boasts comfortable accommodations, multiple entertaining spaces and quick access to Chicago area destinations. With only 20-minutes to O’Hare, 35 minutes to Midway, 25 minutes to downtown and 5 minutes to Oak Brook, you can enjoy world-class shopping, dining, museums, concerts, sporting events and local attractions in one of the “Best Places to Live in America”.

4.96 out of 5 average rating, 69 reviews

Popular amenities for Oakbrook Terrace holiday rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Oakbrook Terrace

Guest favourite
Home in Downers Grove

Springside Retreat: Charming Chicago Suburb

4.83 out of 5 average rating, 40 reviews
Superhost
Home in Bensenville

Fun and Cozy Family Home Near O’hare Airport

4.88 out of 5 average rating, 24 reviews
Guest favourite
The living area features a spacious tan leather sofa positioned around a circular dining table. A large television is mounted on a pink accent wall, and natural light floods the room through expansive windows. A decorative plant sits on the floor, adding a touch of greenery.
Apartment in Westmont

Harmony Haven - 2 Parking Spaces!, Sleeps 4!

4.86 out of 5 average rating, 78 reviews
Superhost
A comfortable living area features a dark sofa, coffee table, and a modern TV stand with a large television. A dedicated dining space with a round table for two is visible. Sliding glass doors lead to a private balcony, providing natural light and outdoor views.
Condo in Lombard

Pond View, Washer Dryer, Non Smoking, Pet Free

4.88 out of 5 average rating, 58 reviews
Guest favourite
Home in Clarendon Hills

Cozy and sunlit retreat in a quiet neighborhood!

4.9 out of 5 average rating, 21 reviews
Top Guest favourite
A spacious ranch house is depicted, surrounded by matured trees and a well-maintained lawn. The facade features a combination of brick and siding, with a large garage and a welcoming front porch. Sunlight filters through the leaves, creating a serene atmosphere.
Home in Itasca

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

4.99 out of 5 average rating, 92 reviews
Guest favourite
A modern kitchen features an island with seating for two and stainless steel appliances. White cabinetry contrasts with a dark backsplash, while large windows allow natural light to illuminate the workspace. The clean design promotes a functional and inviting cooking area.
Home in Elmhurst

Elmhurst NEW - Super Clean Modern Farmhouse!

4.95 out of 5 average rating, 157 reviews
A cozy bedroom features a spacious bed adorned with a patchwork quilt. Soft light from a lamp illuminates the room, complemented by patterned curtains framing a window. A dresser stands nearby, and a glimpse of the bathroom can be seen through an open door.
Apartment in Villa Park

Garden Apt Safe neigh'hood between Airport/Downtwn

4.67 out of 5 average rating, 135 reviews

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