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Holiday rentals in Oak Brook

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Quick stats about holiday rentals in Oak Brook

  • Total holiday rentals

    Explore 20 holiday rentals in Oak Brook

  • Nightly prices starting at

    Oak Brook holiday rentals start at $77 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,140 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Oak Brook holiday rentals include wifi 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 holiday rentals in Oak Brook

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

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Top guest favourite
A bright living area features a comfortable sofa arranged around a modern coffee table. A work desk is positioned near the window, with natural light spilling in. Artwork adorns the walls, and greenery adds a touch of life to the space, enhancing the welcoming atmosphere.
Flat in West Dundee
4.93 out of 5 average rating, 179 reviews

Charming Riverfront Stay | Heart of Downtown

Welcome to The Riverfronts! Three boutique hotel rooms perfectly situated along the river in downtown West Dundee, offering scenic views and modern comforts. ✔ Riverfront Location: Enjoy the scenic riverwalk just steps away. ✔ Prime Downtown Spot: In the heart of downtown Dundee, minutes from top attractions and dining. ✔ Exclusive Group Booking: Reserve just one or all three units for your entire party. ✔ Outdoor Firepit: Unwind by the firepit, perfect for evening gatherings. ✔ Sleeps 4: Each

LocationValueAmenities

Guest favourite
An open living area features a comfortable sofa adorned with patterned pillows, set on light hardwood flooring. A dining space with a table and four chairs is visible. Natural light fills the room, enhancing the modern decor and inviting atmosphere.
Flat in Forest Park
4.92 out of 5 average rating, 102 reviews

Luxurious apartment in great central location!

Welcome to the Troost House. This property is newly remodeled with high end finishes including Quartz counters, hardwood floors and fully equipped with brand-new stainless appliances. This 2BR 1B offers its own laundry room as well as a 1 car garage parking space. Superb location with easy access to major highways, a 5-minute walk to Blue line train station, a 3-minute drive to Loyola Medical Center, a 10-minute drive to DT Chicago, and near the heart of DT Forest Park and historic Oak park.

FamilyLocationCondition

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, 181 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

LocationValueQuiet

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!

ValueFamilyNearby

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.

ValueFamilyNearby

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.

LocationValueIndoor spaces

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
5.0 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.

FamilyValueComfort

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.
Flat 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.

ValueLocationBathroom

Guest favourite
Flat 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.

FamilyValueAccuracy

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, 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!

FamilyLocationKitchen

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, 130 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!

ValueFamilyKitchen

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).

FamilyValueWifi

Popular amenities for Oak Brook holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Oak Brook's top sights

Pappadeaux Seafood Kitchen

18 locals recommend

Go Ape Zipline & Adventure Park

13 locals recommend

Pinstripes

4 locals recommend

Other great holiday rentals in Oak Brook

Guest favourite
Home in Clarendon Hills
4.89 out of 5 average rating, 19 reviews

Cozy and sunlit retreat in a quiet neighborhood!

LocationFamilyBathroom

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

A+: 4BR-3BTH Spacious Home w/ 2 Living Rooms

LocationValueQuiet

Guest favourite
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
4.9 out of 5 average rating, 60 reviews

Beautiful home near the Windy City!

FamilyValueCleanliness

Guest favourite
Home in Warrenville
4.95 out of 5 average rating, 22 reviews

“The Warrenville Grove”

LocationFamilyAccess

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, 79 reviews

Cute & Cozy Lisle, IL House Near the Best Areas

FamilyValueComfort

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, 52 reviews

Comfort Haven

FamilyLocationComfort

Top guest favourite
A spacious living area features modern furniture, including a plush blue sofa and two accent chairs. Unique pendant lights provide ambient illumination, while an open kitchen with a sleek design offers an inviting atmosphere. Large windows allow natural light to fill the space.
Home in St. Charles
4.98 out of 5 average rating, 57 reviews

Luxury Meets Cozy

LocationFamilyIndoor spaces

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

Spacious 4BR Tudor with Patio near Downtown

FamilyLocationCondition

When is the best time to visit Oak Brook?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$234 SGD$230 SGD$288 SGD$284 SGD$379 SGD$352 SGD$316 SGD$345 SGD$255 SGD$264 SGD$307 SGD$282 SGD
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.

Destinations to explore