House holiday rentals in Oak Brook

Home in Glen Ellyn

Beautiful 5 bedroom, 2.5 bath home in Glen Ellyn, fully furnished with everything you may need for a wonderful stay! Located in the peaceful suburbs of Glen Ellyn, the area is perfect for families or friends who would like a comfortable getaway. Located 40 minutes from downtown Chicago and Midway airport and 30 minutes from O'Hare airport. Located nearby major highways and shopping centers. Large, private and completely enclosed backyard perfect for kids to play in or a relaxed evening of BBQ!

Value · Family · Check-in

King beds, firepit, lake view

We may take a refundable deposit. We must say this because our direct booking site is linked. A lovely place on the lake in summer we rent entire house. This is a home that is split into a duplex. One side we have 3 bedrooms 2 baths. The other side is 1 bedroom and 1 bath. Both sides have separate entrances and decks. Enjoy the beautiful view while staying. You have access to entire house and yard except garage with this listing. This listing is for renting both sides. They do not connect.

Value · Family · Indoor spaces

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.

Location · Value · Amenities

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.

Location · Family · Backyard

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!

Value · Location · Outdoor spaces

RetroModern Bungalow | free parking | pet friendly

Experience the city in style at our Retro Modern Bungalow, the perfect pad for up to four friends. Featuring two spacious bedrooms—each with a king bed and luxury linens—a propane fire pit and a pup-friendly, fenced-in backyard. With central HVAC, speedy WiFi, a dedicated workspace, and a pack-n-play crib 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 and catch the train a few blocks away.

Value · Location · Parks

Cozy Ranch w/ King Bed & 3 Baths – Great Location!

Feel at home at this cozy split-level ranch with separate spaces perfect for relaxing—whether you’re staying with family or traveling for work. Watch your favorite show in the basement while someone else is peacefully reading a book on the main level or taking a nap upstairs. Located on a quiet, dead-end street, but just 22 mins from O’Hare Airport, minutes from I-290 and 83rd, and 10 minutes from Oak Brook Mall. Our excellent guest-to-bathroom ratio ensures comfort for everyone!

Location · Value · Air conditioning

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!

Family · Value · Access

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).

Location · Value · Sleep quality

Big 5BR 3.5BA Game Rm Prime Location minutes to DT

Experience ultimate luxury at our exclusive property. Nestled in a prime location, this meticulously designed retreat offers opulent furnishings, panoramic views, and bespoke amenities. Ideal for discerning travelers and work travelers seeking sophistication and comfort, indulge in a private sanctuary where every detail exceeds expectations. Discover the epitome of elegance with us and create unforgettable memories in this exquisite haven.

Location · Family · Access

Oak Park Victorian by FLW Studio

Discover historic charm in our updated 4-bedroom Victorian home in the iconic Frank Lloyd Wright district. Comfortably sleeps 8. Features a fully equipped kitchen, dedicated workspace, and modern amenities. Perfectly located for exploring local gems on foot or a quick 15-min drive to downtown Chicago. Enjoy private parking and easy access to public transit. Ideal for families and groups seeking a stylish, central retreat.

Location · Family · Nearby

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!

Family · Location · Wi-Fi