Vacation rentals in Oak Brook

Guest suite in Saint Charles

A serene riverside scene is captured, featuring calm waters that reflect the colors of a sunset. Lush greenery frames the image, with a large tree on the right and a grassy area leading to the riverbank. Clouds scatter softly across the sky.

4.86 out of 5 average rating, 140 reviews

Cozy, Comfy, Close to Downtown

Discover serenity in our centrally located guest apartment in our charming St. Charles cottage. The space is pet-friendly with a fenced yard, featuring a spacious kitchen, living room, bath, queen-sized bed, and in-unit laundry. The yard offers views of the Fox River, a peaceful patio, friendly ducks, with award-winning parks & biking trails at your doorstep. Note: The unit is studio style located in the lower level of a home. The space is completely private. Only outdoor spaces shared. 😊🦆🪻🏡

4.96 out of 5 average rating, 340 reviews

A lush garden pathway winds through vibrant flower beds and greenery, leading to a cozy seating area nestled under a tree. The stone path is framed by various plants, showcasing a tranquil outdoor setting perfect for relaxation.

Guest suite in West Town

Secret Garden @ The Noble Farmhouse | Wicker Park

While our place truly is a tucked away secret sanctuary, we are also in a sweet spot of ULTRA CONVENIENCE. Wicker Park/Noble Square/West Town has many great bars & restaurants & is an amazing location for exploring the city. WALK to the action on Division St. or Chicago Ave, Chicago's upcoming gallery district. A 1/2 block to the 56 bus takes you to the Loop in 10 min, or to the heart of Wicker Park in 5. A 10 min walk to the BLUE LINE serving O'Hare & Downtown. And Divvy bikes 1/2 block away.

4.92 out of 5 average rating, 256 reviews

The image showcases a serene riverbank along the Fox River, with manicured green grass leading to the water's edge. Two decorative stone vases sit beside a paved area that meets the river, and trees line the opposite bank under a clear blue sky.

Home in South Elgin

Riverfront rental

Riverfront Rental Sits on a quiet street in downtown South Elgin. This home gives you complete access to the Fox River. The bedrooms are on the main level, along with a beautiful kitchen featuring cherry cabinets and an island with breakfast bar, and an awesome four-season porch overlooking the backyard and the beautiful river setting. The second-level loft has great natural light . Outside, you'll find concrete patio and walkway, and stairs leading down to the river and firepit. no pets

Apartment in West Lake View

A spacious living room features large windows allowing natural light to fill the space. A comfortable light-colored sectional sofa is situated in front of a glass coffee table, with a medium-sized rug underneath. A wooden side table and a television mounted on the wall are also visible.

4.94 out of 5 average rating, 179 reviews

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

Welcome to beautiful Roscoe Village! Come relax and enjoy a gorgeous loft-like condo that has a huge sun-drenched living room and opens up right to the kitchen. Enjoy cooking on your own in the spacious kitchen and rest easily at night in a spacious king bed in the main bedroom. We love and welcome pets - so no need to leave your fur baby at home. Uber to Wicker Park and Logan Square. You’ll have your own private entrance with a lock box to get into the condo. We look forward to hosting you!

4.9 out of 5 average rating, 105 reviews

A relaxing outdoor space is depicted at night, featuring a small artisan tiny house and a fire pit surrounded by several chairs. Warm light glows from within the tiny house, and smoke gently rises into the night sky, set against a backdrop of trees.

Guesthouse in Oswego

The Loft-Rustic Retreat and Sauna

This unique space features a beautiful relaxing yard space and easy walking distance to downtown Oswego.. If you need a place to work quietly or stay overnight this is the ideal location to get rest and relaxation, as well as, enjoy the local tranquilities. Antique shopping, River adventures, Bike trails, and more! The Fox River Trail is a few blocks from the Loft and goes North all of the way up to Algonquin. Along the trail is the River where you can tube, kayak, canoe, fish…

5 out of 5 average rating, 13 reviews

A dining area showcases a large wooden table surrounded by eight wooden chairs. A vintage map hangs on the wall, adding character. Natural light enters from nearby windows, illuminating the space. A stylish lamp and greenery are present, complementing the inviting atmosphere.

Home in Avondale

Alluring Avondale Abode

Welcome to Alluring Avondale Abode, the perfect vacation rental for your next family trip or group getaway. A pet-friendly paradise, centrally located for easy travel to all the top attractions. A spacious kitchen, beautiful backyard deck, and patio create a wonderful backdrop for entertaining and relaxing. Find an array of fun games to keep all ages occupied. Book now and experience the laid-back vibe and unbeatable amenities that will make your vacation truly unforgettable.

Apartment in Logan Square

A modern kitchen and dining area features an expansive island with seating for four and an elegant dining table surrounded by stylish chairs. Four skylights allow natural light to fill the space, highlighting the blue walls and contemporary decor.

4.92 out of 5 average rating, 12 reviews

2-level PH w/ 2 Luxe Suites Combined; Spa Access

The top floor sprawling ranch with duplex down offers sky & outdoors views, privacy, & cathedral ceilings, it is connected to your rear 2nd floor suite with 10ft ceilings. A burgeoning neighborhood next to the 606 Trail Amenities: - Uber-fast Wifi streaming, - Hot tub house - 80" + 75" hi-def tv's - 3 sectional couches - European decor - 2 kitchens - The popular 606 Trail access is 100 ft away, - YMCA across the street with indoor Olympic size & kiddie-pools!

5 out of 5 average rating, 8 reviews

A private fire pit area is surrounded by a black wooden fence, featuring six adirondack chairs positioned around a circular stone base. The ground is covered with light gravel, creating a cozy setting for gatherings and relaxation.

Home in Crystal Lake

-NEW- Blue Magnolia Cottage -3 King Beds- Luxury

Blue Magnolia Cottage is a newly renovate 4-Bedroom Home with Luxurious Marble Countertops, Private Backyard Featuring Fire Pit. Ideal for Families and Groups Seeking Comfort and Style. Offering 3 king beds, 1 queen bed and 2 single beds. Spacious Living Areas, Modern Amenities, Zen Den Yoga room and Serene Outdoor Space Make this home your most memorable stay. CHECKOUT OUR OTHER PROPERTIES HERE: www.airbnb.com/p/breganproperties

Guest suite in Naperville

A scenic view of a tranquil lake is framed by vibrant yellow pansies in planters. Lush green grass extends to a black fence bordering the water, while trees and distant greenery create a peaceful backdrop under a blue sky.

4.95 out of 5 average rating, 416 reviews

Cozy Lakeview Studio with Private Access

Enjoy luxury and comfort in this cozy lakefront studio with a private entrance, attached to a home where the friendly hosts reside. The studio offers a plush queen bed, a kitchenette with a mini fridge, microwave, induction cooktop, and a full bathroom. Located in one of Naperville’s safest neighborhoods, it’s just moments from cafes, restaurants, markets, and a biking trail, with easy access to I-88.

4.95 out of 5 average rating, 104 reviews

A modern kitchen features sleek dark cabinetry and stainless steel appliances. Natural light enters through skylights, highlighting a small dining table with two chairs. The warm wood flooring complements the design, while a light fixture hangs gently from the exposed beam ceiling.

Guesthouse in Oak Park

O'Malley Oasis!

Your home away from home at this centrally-located coachhouse apartment.Queen sized bed, fully equipped eat-in kitchen, relaxing living area with recliner, leather couch and big screen tv. Walk to downtown or explore Chicago via public transportation just a few blocks away. Adorable porch and your own entry. Parking spot included!

5 out of 5 average rating, 27 reviews

A covered outdoor seating area is highlighted by a wooden table surrounded by chairs with red cushions. A ceiling fan hangs above, with a view of trees and water visible in the background, enhancing the serene atmosphere.

Home in McHenry

The Oak @ The Oaks On The Fox

Whether you are looking for a relaxing retreat, or to enjoy the local establishments, with live entertainment, or a day of power boating/pedal boating/padddle boarding/kayaking/local horseback riding/hiking/or chilling on your own private beach, you have founded it here! Everything at your fingertips.

4.96 out of 5 average rating, 281 reviews

The exterior of a three-story residential building is depicted, featuring a wooden porch with steps leading to the front door. Large windows allow natural light to enter, and greenery surrounds the entrance, complementing the light-colored siding and red brick foundation.

Apartment in Irving Park

Spacious 1BR apartment in a central location

Private 1BR in Avondale neighborhood of Chicago. Right off the Expressway, it's 20 mins from O'Hare, 20 mins from Downtown (both by Blue Line) 20 mins from Wrigley Field (bus). Comfortable and spacious attic apartment in a residential area. Lots of street parking.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Hotels

Stylish accommodations and amenities

Popular amenities for Oak Brook vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Oak Brook's top sights

Oakbrook Center31 locals recommend

Oakbrook Mall station11 locals recommend

Trader Joe's9 locals recommend

Yorktown Center10 locals recommend

Chipotle Mexican Grill6 locals recommend

Pappadeaux Seafood Kitchen11 locals recommend

Apartment rentals in Oak Brook

4.97 out of 5 average rating, 108 reviews

A cozy living area features a modern black sectional sofa adorned with colorful throw pillows. A large photograph of a city skyline hangs on the wall. A small coffee table rests on a patterned rug, while a desk and chair are positioned beside a plant and shelves.

Apartment in Avondale

Lovely 2bedroom 1bath Apt and outdoor seating.

Apartment in Saint Charles

A functional kitchen space features wooden cabinetry and stainless steel appliances. A gas stove and sink are positioned alongside a counter with decorative dishware. Dining utensils are arranged on the counter, creating an inviting environment for meal preparation and dining.

4.93 out of 5 average rating, 161 reviews

Beautiful St. Charles 3 Bedroom 1 1/2 Bath Apt.

4.83 out of 5 average rating, 179 reviews

A welcoming living space features a round dining table surrounded by four chairs, with a large artwork depicting trees on the wall. A light fixture hangs from the ceiling, and a mirror reflects the room. Natural light fills the area, enhancing the warm ambiance.

Apartment in Evanston

MDRN Kid-Frndly Apt | Natural Lite | Quiet|Private

4.82 out of 5 average rating, 185 reviews

A modern living area features a beige sectional sofa and a round coffee table set on a patterned rug. A large flat-screen TV is mounted on the wall, and a potted plant adds a touch of greenery. Natural light illuminates the space.

Apartment in Chinatown

New apartment

Apartment in East Rogers Park

An outdoor terrace is visible, featuring seating arrangements with two orange chairs and a fire pit. The view overlooks Lake Michigan, with the calming waves in the background. A pathway leads down to the water, surrounded by the building's architecture.

4.89 out of 5 average rating, 169 reviews

Executive Apartment on Lake Michigan with parking

4.98 out of 5 average rating, 214 reviews

A spacious living area is furnished with a dark sectional sofa, accented by decorative pillows. A round coffee table rests on an area rug, while a television is placed on a dark wooden stand. Natural light filters through large windows with sheer curtains.

Apartment in Chicago

Chicago Airbnb Newly Remodeled 2-Unit Apartment!

Apartment in Roscoe Village

A bright living room is highlighted by large windows that invite natural light. A comfortable brown leather sofa and a beige loveseat are positioned around a colorful area rug. A wooden coffee table and a wall-mounted TV complement the inviting space.

4.97 out of 5 average rating, 147 reviews

Inviting 2 Bedroom Apartment in Roscoe Village

4.92 out of 5 average rating, 212 reviews

A comfortable living room features a gray sofa adorned with patterned cushions, positioned beside a light wood coffee table. A television is set on a dark wood stand, while decorative shelves and a stool add functionality to the space. Natural light enters through a window, illuminating the room.

Apartment in Geneva

Vintner's Attic- downtown Geneva!

Show all

Other great vacation rentals in Oak Brook

5 out of 5 average rating, 51 reviews

A bright living area is showcased with large windows that invite natural light. Comfortable seating arrangements are provided by two armchairs and a spacious sofa. A rustic rug anchors the space, complemented by a decorative coffee table and a bench along the staircase.

Home in Schaumburg

Great location-King beds-Kids playroom

Guest suite in Lincoln Park

An exterior view of a charming blue building with a staircase leading to the entrance. A spacious outdoor area features a large table surrounded by several chairs, complemented by surrounding greenery and decorative plants. Trash bins are located to one side.

4.8 out of 5 average rating, 10 reviews

The Hidden Beach House

Guest suite in Plainfield

A concrete pathway leads to a grassy area, bordered by a white fence, with several planters on both sides. The planters include a tall, woven design and a smaller, elegant style, featuring greenery that adds a touch of nature to the outdoor space.

4.86 out of 5 average rating, 80 reviews

Relaxing Suite with Independent Entrance

4.86 out of 5 average rating, 42 reviews

A modern kitchen features sleek white cabinetry and stainless steel appliances. A large granite island provides additional workspace and seating. Natural light from the windows brightens the space, while a dining area with wooden chairs is visible in the foreground.

Apartment in Albany Park

Elegant 4Bedroom with Free Parking in Albany Park

Apartment in Jefferson Park

A modern kitchen is equipped with sleek stainless steel appliances, including a microwave and dishwasher. Light countertops complement dark cabinetry, while a small countertop with two barstools provides a casual dining option. Natural light filters in through a window near the door.

4.62 out of 5 average rating, 26 reviews

City Gem: Stylish 3BR for Urban Explorers

4.84 out of 5 average rating, 100 reviews

A modern kitchen is equipped with stainless steel appliances and white cabinetry. Natural light fills the space through two large windows. A white farmhouse sink is complemented by a dark wooden countertop, while a patterned rug lies on the hardwood floor.

Home in Logan Square

California Cottage/4br prime location Logan Square

5 out of 5 average rating, 22 reviews

A modern kitchen features sleek gray cabinetry and a white countertop. Stainless steel appliances are prominent along the back wall, and a window provides natural light over a farmhouse sink. Decorative tile backsplash adds texture, complemented by ample space for meal preparation.

Home in Elgin

Little Blue House