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 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, 218 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
Home in Villa Park
4.91 out of 5 average rating, 43 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 bright living area is filled with comfortable seating, including two armchairs and a spacious sofa. A light area rug with a geometric pattern covers the floor. Natural light streams in through large windows adorned with wooden blinds, and a decorative tray sits on a plush ottoman.
Home in Lombard
4.97 out of 5 average rating, 59 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.

Superhost
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
5.0 out of 5 average rating, 135 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
4.58 out of 5 average rating, 24 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.

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
4.78 out of 5 average rating, 156 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 light-filled living room features a spacious gray sectional sofa arranged around a simple coffee table. Large windows provide views of the outdoor space while soft curtains frame the light. A flat-screen TV is mounted on a textured wall, enhancing the room's modern design.
Home in Lombard
5.0 out of 5 average rating, 48 reviews

Grand Retreat/5Brs/Game Room

Welcome to the Grand 5-bedroom, 2-bath home in Lombard, IL – perfect for families or groups seeking comfort and entertainment! Inside, enjoy 5 TVs and a heated garage transformed into a gaming room with a pool table, PAC-Man, basketball, and board games for endless fun. Step outside to relax in the fully fenced yard with a grill, ideal for outdoor dining. The kitchen is fully stocked for all your cooking needs. Conveniently located near highways, shopping, and dining.

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
4.93 out of 5 average rating, 164 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!

Guest favourite
The collage showcases various areas of the property, including a modern living space with a wall-mounted TV, a two-story exterior featuring stone details, an outdoor patio area with seating under a pergola, a game room equipped with a ping pong table, and a bathroom with a jacuzzi tub and neatly arranged towels.
Home in Westchester
4.96 out of 5 average rating, 131 reviews

Jacuzzi, King Beds, Easy Access to DT Chicago!

Our 4bd, 2.5ba house is perfect for a group of friends or family looking for a clean, modern place in a wonderful neighborhood. There is plenty of space for 10 people to sleep comfortably (4 beds), as well as 4 smart TVs, a deck w/ a pergola, built-in grill, & firepit, a large fenced backyard, a game room (w/ ping pong and more), a jacuzzi, an office space, & much more. Great access to City of Chicago by I-290, as it's directly west of Downtown!

Guest favourite
Home in Elmhurst
4.92 out of 5 average rating, 122 reviews

Big 5BR 3.5BA Game Rm Prime Location minutes to DT

Experience ultimate luxury at our exclusive property. Nestled in a prime location, this meticulously designed retreat offers opulent furnishings, panoramic views, and bespoke amenities. Ideal for discerning travelers and work travelers seeking sophistication and comfort, indulge in a private sanctuary where every detail exceeds expectations. Discover the epitome of elegance with us and create unforgettable memories in this exquisite haven.

Superhost
Home in Lombard
5.0 out of 5 average rating, 15 reviews

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.

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
4.99 out of 5 average rating, 155 reviews

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

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.