Holiday rentals in Oak Brook

4.86 out of 5 average rating, 118 reviews

Flat in Forest Park

City-Accessible Basement Retreat

Discover a perfect mix of small-town charm and city life in this cozy basement unit. Situated just a 7-minute walk from the train station, downtown Chicago is easily accessible for work/leisure. The neighborhood is a treasure trove of local restaurants, bars, and stores, ensuring you're never far from what you need. A convenient gas station/store is right behind your home for quick needs. Ideal for a simple, connected lifestyle with the city’s pulse at your doorstep. Your urban retreat awaits!

Guest suite in Brookfield

5 out of 5 average rating, 103 reviews

Charming Chicago suburb! 1 bedroom apartment.

Enjoy your stay just west of Chicago in our 1880 updated 1st floor of a 2 flat. You get a one bedroom apartment with queen bed, private kitchen and bath, separate office for work, plus 2 porches for you to enjoy. Brookfield is a charming village with unique restaurants, bars, salon and day spa, coffee shops, library and the train to Chicago--all within a 5 minute walk. We want you to feel at home; but before you book understand that you may not smoke ANYTHING in the unit or on the property.

5 out of 5 average rating, 29 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.

4.99 out of 5 average rating, 659 reviews

Guest suite in Geneva

A Suite within a Cozy cottage in Geneva Illinois.

Cozy private suite in the lower level. Guests have the suite to themselves. The bathroom is adjacent to the room and is private. There is a small fridge, a coffee maker, and a microwave oven. We are in Geneva, Illinois. We are LGBTQ+friendly. Our space is ideal for shorter stays and visitors on the go . Not suitable for staycations. Quiet area. Hosts live on the upper level and guests pass through our space to get to the suite. In a bind we can accommodate a 3rd guest and a pet. Welcome.

4.82 out of 5 average rating, 122 reviews

Flat in Oak Park

Circle Back Modern Apartment

Sit on your leafy private patio and enjoy your coffee before heading out to the city- or wind down at the end of the day with a cold beer. Steps to coffee shops, neighborhood pubs, and the Blue Line train this beautifully updated and decorated apartment is the perfect landing pad for your Chicago adventure. FREE off-street parking, free in-unit laundry, a cute coffee station- basically every amenity we could think of! This will be the place you want to stay every time you visit Chicago.

4.99 out of 5 average rating, 155 reviews

Flat in Aurora

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.

4.86 out of 5 average rating, 139 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!

4.98 out of 5 average rating, 233 reviews

Flat in Forest Park

Walk to Oak Park from this Newly Remodeled Gem

This is an open, bright and comfortable home that has been fully renovated, but still has the historic charm of an older house (early 1900s). With a completely updated kitchen you have everything you need to fix a good meal or you can choose to eat out at one of the many restaurants and bars/brew pubs within close proximity. The apartment has an office nook with a desk and chair for getting your work done, or you can kick back and relax in the living and dining spaces.

5 out of 5 average rating, 12 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 3 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.

5 out of 5 average rating, 3 reviews

Flat in Berwyn

NEW Jade Haven in Berwyn/Riverside

Step into Jade Haven, where tranquility meets modern elegance. This serene one-bedroom, one-bath suite offers a peaceful retreat, inspired by the calming essence of jade. The space features a sleek, airy design with thoughtful touches to make you feel right at home. Fully equipped kitchen, cozy living area, the bedroom invites restful nights, while the spa-like bathroom offers a moment of quiet indulgence. Perfect for a restful getaway or a productive stay.

Guest house in Villa Park

4.92 out of 5 average rating, 121 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!

4.99 out of 5 average rating, 115 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 Oak Brook holiday rentals

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Other great holiday rentals in Oak Brook

4.99 out of 5 average rating, 138 reviews

Private room in Elmhurst

Cozy room with private bathroom.

RiyaRating, 5 stars1 week ago

We had a wonderful stay at this beautiful home, 30 min away from Chicago downtown which came equipped with all the basic amenities we needed for a comfortable visit. The house was spotless, the bed was cozy, and the neighborhood was quiet and pleasant perfect for a relaxing getaway. The hosts were incredibly warm and welcoming. They gave us a quick tour of the place upon arrival, making sure we felt at home. They were flexible with our late checkin and In the mornings, they offered us breakfast, which was a lovely touch. They also went out of their way to suggest local tourist spots, including some great tips and tricks for finding parking downtown — something we really appreciated. Having a dedicated parking spot in the driveway was super convenient, especially after long days of exploring. Overall, the hospitality, cleanliness, and thoughtful touches made this a truly memorable stay. We’d definitely love to return and highly recommend this place to anyone visiting the area.

Private room in Franklin Park

4.96 out of 5 average rating, 126 reviews

Safe & Clean King size Bed Next to Ohare/Rosemont

PhoebeRating, 5 stars2 weeks ago

Joswe was so incredibly kind and accommodating! Being a solo traveler it felt like a home away from home. The space was clean and comfortable and felt very safe. Joswe even left freshly brewed hot coffee every morning along with breakfast! I couldn't recommend Joswe or his home enough! if I could give more stars, I would!

4.8 out of 5 average rating, 363 reviews

Hotel room in Itasca

King Bed at Chicago Northwest + PET Friendly

JenniferRating, 5 stars2 weeks ago

had a wonderful stay. would stay again.

Private room in North Riverside

4.93 out of 5 average rating, 215 reviews

The Albany Park Room at the Cape Cod in Riverside

GianfrancoRating, 5 stars1 week ago

I had an amazing experience staying at this Airbnb! From the moment I arrived, everything exceeded my expectations. The space was spotless, beautifully decorated, and exactly as described—if not better. The bed was incredibly comfortable, and all the little touches (like fresh towels and local recommendations) made it feel like a home away from home. The host was outstanding—friendly, responsive, and genuinely committed to making sure I had a great stay. Check-in and check-out were seamless, and they went above and beyond to accommodate any questions I had. The location was perfect: quiet and peaceful, but still close to restaurants, shops, and everything I wanted to explore. Whether you’re traveling for business or a getaway, I highly recommend this place. I’ll definitely be coming back!

4.92 out of 5 average rating, 273 reviews

Hotel room in Rosemont

Relaxing Standard Room l Free Airport Shuttle

AlexeiRating, 5 stars2 weeks ago

easy check-in, super clean, friendly staff. parking is easy and affordable. will definitely be staying again!

Flat in Forest Park

5 out of 5 average rating, 9 reviews

Luxurious Lifestyle

ArielRating, 5 stars2 days ago

Restful, clean, beautiful, and low-stress! Great visit!!

Private room in Woodridge

4.86 out of 5 average rating, 499 reviews

Private floor with Bedroom, bathroom, living rm

NecoleRating, 5 stars5 days ago

Taylor's place was very nice; she really thought of everything. Everything you could need was there; Taylor makes you feel right at home. The neighborhood is nice and you're close to a number of things. Oh and the shower pressure was great!