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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 treehouse elevated above ground showcases a wooden exterior with a balcony. An inviting staircase leads to the entrance, surrounded by lush greenery and vibrant leaves creating a natural setting. The sturdy structure is supported by wooden beams, blending harmoniously with the surrounding trees.
Treehouse in Schaumburg
4.94 out of 5 average rating, 886 reviews

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!

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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.

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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.

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Guest favourite
The exterior of a single-story home is framed by lush green grass and dark mulch landscaping. A welcoming pathway leads to the front door, adorned with a seasonal wreath. A large tree provides shade, and a white fence marks the boundary of the yard.
Home in Naperville
4.86 out of 5 average rating, 180 reviews

Dog Friendly Cozy North Naperville 3 BED/2 BA Home

Welcome to the Naperville Nest! Rare North Naperville opportunity to find a home suited for the whole family! Pets are more than welcome to enjoy the 1/2 acre fully fenced in yard. This is a a fully updated home minutes from Downtown Naperville, I-88 and many more exciting destinations in the Western Suburbs. You will feel at home whether you're inside or outside...each bedroom has it's own TV and the outdoor living includes natural gas firepit & grill/dining table...this home has it all!

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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
5 out of 5 average rating, 133 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.

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Superhost
Home in Elmhurst
4.59 out of 5 average rating, 22 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.

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Top Guest favourite
A spacious living area features a corner sectional sofa with soft cushioning and a cozy throw. Large windows provide natural light and city views. A simple coffee table sits in front, with light-colored carpet underfoot, enhancing the comfortable atmosphere.
Apartment in Aurora
4.98 out of 5 average rating, 277 reviews

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.

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Guest favourite
Apartment in Maywood
4.93 out of 5 average rating, 251 reviews

Cozy guest studio, great for couples!

This unique place has a style all its own. Enjoy this beautiful, cozy guest studio with modern touches and well furnished living area, small kitchenette with mini fridge and microwave to reheat a quick bite before heading to the city, full bathroom with rainfall shower and handheld sprayer to help you relax after a long day. Flat screen TV with Xfinity streaming device so you can connect your accounts and enjoy your favorite shows and movies for a quiet stay in.

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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
4.93 out of 5 average rating, 162 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!

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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, 103 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).

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Top Guest favourite
The living area features a comfortable seating arrangement with a sofa and two armchairs. A round coffee table sits in the center on a patterned area rug. Soft lighting enhances the neutral wall tones, while a decorative plant adds a touch of greenery.
Apartment in Warrenville
4.94 out of 5 average rating, 132 reviews

“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!

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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, 151 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!

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Popular amenities for Oakbrook Terrace holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Oakbrook Terrace

Top Guest favourite
A geodesic dome home is nestled among lush green trees, featuring a sloped roof and large windows that invite natural light. The surrounding yard is manicured with grass and bordered by colorful flower beds, creating a serene outdoor space.
Dome in Naperville
4.93 out of 5 average rating, 100 reviews

Professionally Sanitized - Dome Away From Home

LocationFamilyComfort

Top Guest favourite
An open living area features a spacious, L-shaped sectional sofa with decorative pillows arranged around a wooden coffee table. A patterned area rug is beneath, and natural light filters in through large windows. A dining area with a table and chairs is visible in the background.
Home in Lombard
4.98 out of 5 average rating, 49 reviews

The Westmore Retreat

ValueFamilyBackyard

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
4.92 out of 5 average rating, 59 reviews

Cozy 2 bedroom home in a wonderful neighborhood.

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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
4.87 out of 5 average rating, 55 reviews

Pond View, Washer Dryer, Non Smoking, Pet Free

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Guest favourite
A cozy bedroom features a spacious bed dressed in floral bedding, complemented by pastel pillows. Two nightstands frame the bed, and a light-colored rug covers the floor, adding warmth to the neutral walls. Soft lighting is provided by recessed ceiling fixtures, enhancing the serene ambiance.
Home in Woodridge
4.84 out of 5 average rating, 90 reviews

Private Apartment • Ground Floor • Free Parking

LocationFamilyAccuracy

Guest favourite
A comfortable living area features a light gray sofa positioned next to a white entertainment unit. A flat-screen TV is mounted on the wall, and a large area rug with intricate patterns covers the hardwood floor. Natural light from the windows brightens the space.
Home in Lisle
4.92 out of 5 average rating, 78 reviews

Cute & Cozy Lisle, IL House Near the Best Areas

LocationFamilyWi-Fi

Guest favourite
Home in Westmont
4.95 out of 5 average rating, 43 reviews

King beds, firepit, lake view

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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
4.95 out of 5 average rating, 152 reviews

Elmhurst NEW - Super Clean Modern Farmhouse!

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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