Vacation rentals in Oakbrook Terrace

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Top-rated vacation rentals in Oakbrook Terrace

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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

4.91 out of 5 average rating, 131 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

Guest favorite

A spacious living area is highlighted by a black sofa facing a light-colored coffee table. A vibrant area rug adds color underfoot. The walls are adorned with colorful vinyl records and framed artwork, while original woodwork details frame the open layout leading to the dining area.

Apartment in Oak Park

4.86 out of 5 average rating, 688 reviews

Rockin' 2Bed steps to shops/food/train

This musically-inspired vintage 2 BR is perfectly placed in Oak Park and we know you'll have a rockin' vacation here. Steps to shops, cafes, train, and FL Wright home. With a cassette wall, reading nook, and many other cute touches. The apartment is a vintage brownstone with charming details, like original woodwork. Street parking available. Easy access to Chicago.The place is an older Chicago brownstone, with a lived-in feel. NO PARTIES!! Upstairs neighbors can be heard walking and moving

Top guest favorite

A fenced backyard features a circular arrangement of wooden lounge chairs centered around a propane fire pit, creating a cozy gathering space. Twinkling string lights hang above, illuminating a bistro table with two blue chairs. Lush green grass surrounds the stone patio area.

Home in Berwyn

4.98 out of 5 average rating, 169 reviews

Retro Modern Bungalow | fire pit | free parking

Experience the city in style at our Retro Modern Bungalow, the perfect pad for up to 4 friends. Featuring two spacious bedrooms—each with a king bed and luxury linens—a propane fire pit and a fully fenced, pup-friendly backyard. Enjoy central HVAC, speedy WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage or catch the train a few blocks away.

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

4.95 out of 5 average rating, 38 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

Double French doors open into a bright, inviting living space. A patterned area rug lays on polished hardwood floors, leading to a cozy seating area with upholstered chairs. Decorative artwork adorns the walls, and soft light filters in through the windows.

Apartment in Oak Park

4.94 out of 5 average rating, 180 reviews

A Quiet Stay While You Are Away Oak Park

Welcome to our cozy and comfortable home located in a quiet neighborhood. Our space is perfect for couples, solo travelers, small families, and long-term stays. This is a beautiful, modernist home located in the Frank Lloyd Wright District Neighborhood, a designated historic district known for its collection of homes designed by the famous architect Frank Lloyd Wright. This district features a collection of some of his iconic designs and is a destination for architecture enthusiasts.

A spacious living area is presented with a large teal sectional sofa, accented by orange chairs. A round, metallic coffee table sits atop a striped rug. The open layout leads into a modern kitchen, visible in the background, with bright lighting and stylish decor.

Home in Oakbrook Terrace

4.7 out of 5 average rating, 70 reviews

Desirable chic home in a Prime Location!

Welcome to this beautifully renovated charming home in Oak Brook Terrace! This home is a lovely getaway for a family or a group! This location is prime and is within waking distance to a variety of restaurants & shops. Also close to shopping and activities in Oak Brook. We are located only 17 miles from downtown Chicago and only 25 minutes from O’Hare and Midway International Airports. We are only 10 minutes from the Metra Station and conveniently located by four major expressways!

Top 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, 193 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.

Guest favorite

A single-story house features a welcoming entrance with a front step and decorative wreath. Inside, cozy sleeping areas include both a queen bed and twin bunk beds. A smart TV displays a cityscape, while a dining table with six chairs is ready for meals.

Home in Lombard

4.86 out of 5 average rating, 155 reviews

Comfy Home w Access to Major Roads/Hwys, Huge Yard

Our house is perfect for a small group of friends or family looking for a clean, accessible place. It contains 3 bedrooms (2 queen bed & twin bunk beds) & 1 full bathroom, as well as a sleeper sofa with a pullout queen bed. Enjoy complimentary Netflix & Hulu with our smart TVs, grill or warm up by the fire pit, & even get some work or studying done! Located just minutes from major highways, parks, museums, & Yorktown Center, the journey is just getting started once you arrive!

Guest favorite

A serene lakeside view is presented, featuring a sunset reflecting on calm waters. Decorative string lights hang above a deck, while various seating options are arranged around. The backdrop includes silhouettes of homes and lush greenery along the shoreline.

Townhouse in Westmont

4.98 out of 5 average rating, 43 reviews

One King bedroom, views, Full kitchen

1 King bedroom and hall bath. Private deck. Other rooms will be locked. For more beds please visit our other listings for this home. Parking available for 2 cars in driveway. This home is a house split in two and the other side is separate unit with its own exterior door. The units do not connect inside anymore and is double drywalled up over a locked metal door similar to connecting hotel rooms. Wonderful safe neighborhood. Well stocked kitchen for nearly anything you need.

Superhost

A workspace is featured against a dark blue wall, showcasing a wooden desk with a laptop and a round mirror above. A stylish floor lamp provides soft lighting, while potted plants add a touch of greenery on either side.

Apartment in Lombard

4.78 out of 5 average rating, 55 reviews

Serenity & Style, With Parking

Unwind in this serenity & cozy style retreat, designed for ultimate comfort! Enjoy a Queen bed and a Full-size sleeper sofa, perfect for a restful stay. Stream your favorites on the 65” living room TV or the 43” bedroom TV with ROKU access (HBO Max, Netflix & more). Stay connected with lightning-fast Wi-Fi, cook with ease in the fully stocked kitchen, and enjoy the convenience of 1 FREE parking space plus a coin washer & dryer in the building. Your getaway starts here!

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, 136 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 favorite

A walkway lined with pavers is framed by greenery, leading toward a fenced yard. Soft string lights illuminate the area beside the tiny house, creating a serene evening atmosphere. A cozy seating area is visible, inviting relaxation outdoors near the lush foliage.

Tiny home in Burr Ridge

4.9 out of 5 average rating, 402 reviews

Less is more! Pet friendly Tiny Home near Chicago!

Less is more--see for yourself how big 250 square feet can really feel! For those who would love to try tiny living and a minimalist lifestyle, this is the perfect getaway. This tiny house has everything you will need to fall in love with tiny living! There is a fenced yard, grass area for furry friends, free parking and is close to hiking trails, restaurants, shops, breweries, bars, and Chicago! Check us out on Insta: @LessIsMore_TinyHome