Vacation rentals in Oak Brook

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Quick stats about vacation rentals in Oak Brook

  • Total vacation rentals

    Explore 20 vacation rentals in Oak Brook

  • Nightly prices starting at

    Oak Brook vacation rentals start at R 988 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 1,140 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Oak Brook vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Oak Brook rentals

  • 4.8 Average rating

    Oak Brook stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated vacation rentals in Oak Brook

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

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Guest favorite
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, 176 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

Top guest favorite
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, 56 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.

Guest favorite
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
4.85 out of 5 average rating, 179 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!

Top guest favorite
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, 128 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.

Guest favorite
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, 274 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.

Top guest favorite
Apartment in Maywood
4.93 out of 5 average rating, 247 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.

Guest favorite
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
4.92 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 favorite
A glass of red wine is positioned in the foreground, reflecting the soft colors of the sunset over a calm lake. The shoreline is bordered by tall grasses, framing the tranquil water and vibrant sky.
Townhouse in Westmont
4.87 out of 5 average rating, 132 reviews

Westmont 3/2 duplex Fire sunsets, Firepit, lake

Near great shopping and dining. Enjoy wonderful sunsets and quiet lake activity. Fully Stocked 20 acres lake with a neighborhood beach next door. Easy commute to downtown while enjoying the peace and quiet. Feel like you are on vacation every day. Perfect for a staycation. Cleaned to Cdc standards. This duplex is a gem in Western suburbs! Pet friendly (fee). Fire pit (bring Wood), paddleboat, kayaks. Grill and fully stocked kitchen.

Top guest favorite
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, 129 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!

Guest favorite
A modern kitchen is showcased with dark cabinetry and a contrasting light countertop. Stainless steel appliances, including a refrigerator, microwave, and oven, are featured. A patterned tile border adds visual interest to the space, while large windows provide natural light.
Home in Brookfield
4.91 out of 5 average rating, 55 reviews

Beautiful home near the Windy City!

Bring the whole family to this great place with lots of room for fun. We are located 10 miles from Downtown Chicago. Plenty of sightseeing and activities. We are less than a 5-minute walking distance from one of the well-known old-school arcades in the Chicagoland area. Downtown La grange is within walking distance with plenty of coffee shops, restaurants and shopping. The historical Brookfield Zoo is a 10-minute drive.

Top guest favorite
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, 150 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 Oak Brook vacation rentals

When is the best time to visit Oak Brook?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR 3,013 ZARR 2,964 ZARR 3,705 ZARR 2,783 ZARR 3,293 ZARR 3,886 ZARR 4,067 ZARR 4,446 ZARR 3,277 ZARR 3,392 ZARR 3,952 ZARR 3,622 ZAR
Avg. temp-4°C-2°C4°C10°C16°C21°C24°C23°C19°C12°C5°C-1°C

Frequently Asked Questions

  • What are the best places to stay in Oak Brook?

    Accommodations in Oak Brook include homes near shopping centers, tree-lined neighborhoods, or areas close to parks. Family-friendly rentals and suites are commonly available around Oakbrook Center.

  • What are the best things to do in Oak Brook with kids?

    Children often enjoy hands-on experiences at Fullersburg Woods Nature Center, playful afternoons at local parks, and browsing shops or sweet treats at Oakbrook Center. Family-friendly events and mini-golf are frequently suggested.

  • What are some of the best things to do in Oak Brook?

    Explore luxury shops and restaurants at Oakbrook Center, walk the scenic trails at Fullersburg Woods Nature Center, or visit the historic Mayslake Peabody Estate. Outdoor golf and family activities are frequently suggested.

  • How is the weather in Oak Brook?

    Oak Brook has cold winters near 19–32°F (-7–0°C), warming to mild springs and summers around 51–85°F (10–29°C). Rain is more frequent in the spring, so packing for wetter months is helpful.

  • When is the best time to visit Oak Brook?

    Late spring through early fall is often recommended for outdoor activities and milder temperatures around 50–80°F (10–27°C). Seasonal festivals and art shows add vibrant experiences during these months.

  • What are the best places to visit in Oak Brook?

    Explore the Oakbrook Center for shopping and dining, stroll the paths at Fullersburg Woods Nature Center, or visit the Mayslake Peabody Estate. The area also has parks and golf courses for outdoor activities.

  • What are some hiking trails in Oak Brook?

    Fullersburg Woods Nature Center has scenic trails winding through woodlands and along waterways. Mayslake Peabody Estate features quieter paths, and local parks offer walking and jogging routes for all ages.

  • What are some family activities we can do in Oak Brook?

    Families often explore Oakbrook Center, hike at Fullersburg Woods Nature Center, or visit local playgrounds and golf courses. Seasonal outdoor events and art programs are also popular with kids and adults.

  • What are some of the best day trip ideas from Oak Brook?

    Day trips from Oak Brook can include exploring nearby botanical gardens, visiting museums in surrounding cities, or discovering historic neighborhoods and lakefront parks. Seasonal outdoor festivals are also frequently suggested.

  • Are there any pet friendly accommodations available in Oak Brook?

    Many accommodations in Oak Brook welcome pets, making it easy to bring furry friends along for your stay. Green spaces around the area encourage walks and pet-friendly outings.

  • What are some local tips for visiting Oak Brook?

    Locals suggest arriving early for weekend shopping or special events and exploring nature trails for a quiet escape. Try locally owned restaurants for distinct flavors, and check for outdoor concerts during warmer months.

  • What is Oak Brook known for?

    Oak Brook is known for its upscale shopping at Oakbrook Center, expansive parks, and corporate offices. The community has well-maintained green spaces and historic sites, often drawing families and business travelers.

  • What are the best hidden gems to explore in Oak Brook?

    Discover tranquil trails in Fullersburg Woods, quiet garden spots at Mayslake Peabody Estate, or locally owned cafes tucked around Oakbrook Center. Small art galleries and historical sites often surprise visitors with unique stories.

  • What are the best foods to try in Oak Brook?

    Oak Brook is known for American classics, Italian fare, and contemporary cuisines often found in local restaurants. Families frequently enjoy hearty burgers, wood-fired pizzas, and seasonal salads.

  • What should I bring for a trip to Oak Brook?

    Pack comfortable clothing, a light jacket for cooler evenings, and a raincoat during wetter months. Shoes suitable for walking around shopping centers or nature trails are frequently recommended.

  • What is the nightlife in Oak Brook like?

    Nightlife in Oak Brook centers around laid-back lounges, lively bars, and late-night dining in and near Oakbrook Center. Those seeking entertainment can enjoy live music or gatherings in casual venues.

  • What are the most popular events or festivals in Oak Brook?

    Oak Brook has annual art fairs, local food festivals, and outdoor summer concerts that are often recommended. Seasonal celebrations and community gatherings around public spaces bring residents and visitors together throughout the year.

  • Are there family friendly vacation rentals in Oak Brook?

    Oak Brook has vacation rentals suitable for families, with spacious layouts and amenities like kitchens and multiple bedrooms. The area is known for parks and shopping centers that families often enjoy together.

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