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Holiday houses in Oakwood Beach

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Oakwood Beach

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

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Guest favourite
Home in Chicago
4.92 out of 5 average rating, 26 reviews

Luxury 4BR w/ Spa Tub Near UChicago & Obama Center

Discover Metra Haven, a luxury thoughtfully designed 4BR near Hyde Park, this home is ideal for bachelorette weekends, girls trips, family gatherings, professionals or large groups seeking cozy comfort Unwind in the spa-style bath tub, gather in the private backyard patio, with fire place for cozy evenings accommodating your group Steps from Metra station with a direct train to Downtown, 4mins away from the Obama presidential center in Jackson pack, museum of science & industry and the lake

Guest favourite
A spacious living area features high ceilings with a skylight and large windows, offering ample natural light. A comfortable green sofa and a black armchair are positioned near a coffee table. A fireplace and a television are visible, with scenic views seen through the glass doors.
Apartment in Chicago
4.96 out of 5 average rating, 68 reviews

Sunny Penthouse - Oakwood Beach

Bright top-floor 2-bedroom, 2-bath condo in the heart of Bronzeville with soaring ceilings and abundant natural light. Relax in the in-unit jacuzzi jetted tub after a day exploring Chicago. The fully equipped kitchen has everything you need to cook at home, or enjoy nearby restaurants. 🌊 Just a 18-minute walk to Oakwood Beach & the lakefront. Within a 20-minute drive of Downtown, Soldier Field, Guaranteed Rate Field, the Field Museum, the Art Institute, Chinatown, Hyde Park, Pilsen & more!

Superhost
A view of the Chicago skyline features tall buildings rising in the background, while numerous boats are docked in the foreground. The clear blue water reflects the cityscape under a bright sky.
Guest suite in Chicago
4.76 out of 5 average rating, 42 reviews

Large Minimalist Garden Studio: Centrally Located

Need a cozy, unique, convenient, & affordable place to stay? Look no further, this may be the perfect spot for you! Located in the heart of Historic Bronzeville, just minutes from downtown Chicago, McCormick Place Convention Center, Illinois Institute of Technology, Sox Stadium, & only 1.2 miles from the University of Chicago, this spacious & serene retreat offers the ideal escape. Relax, recharge, and leave your worries behind in a space thoughtfully designed for your comfort and convenience.

Guest favourite
Apartment in Chicago
4.9 out of 5 average rating, 21 reviews

Cozy Coach House Apartment-Near Downtown Chicago

Relax at this peaceful private entrance stay in the historic North Kenwood neighborhood right next to Hyde Park! Centrally located, blocks from the lake front, next to pickle ball park, 7 min drive to UChicago campus, and 8 mins drive to the world renowned, Museum of Science and Industry! A short walk to the Metra Train/buses to downtown, 12 min drive to downtown Chicago (6 miles), 10 min drive to McCormick Place (3.5 miles), and 9 min drive to the new Obama Presidential Center (2 miles)!

Superhost
Home in Chicago
4.85 out of 5 average rating, 59 reviews

Lux Home Chicago 7mins Downtown

Come stay at our luxurious 2-story newer construction home in Chicago. This centrally located, gated, 4 Bedroom, 5Beds, 3 1/2 bath home is ideal for family vacation, work or leisure trips. It comes with a full upscale gourmet kitchen and a spacious fully furnished basement with gym equipment. It is just a 7mins drive to the best attractions in Chicago, including the beach and museums; close to numerous restaurants, nightlife, and major highways for easy travel and access around the city.

Top Guest favourite
A modern living space features a light-colored sofa with decorative pillows and a woven throw. A warm-toned wooden accent wall complements a sleek electric fireplace below a mounted television. A patterned area rug anchors the room, while shelves in the background display decorative items.
Loft in Chicago
4.99 out of 5 average rating, 150 reviews

Lovely Garden Studio in Chicago

Kick back and relax in this calm, stylish space. Located in historic Bronzeville, our modern studio boasts open-plan living, stylish finishes and plenty of room to accommodate up to 3 guests. Our garden studio is located walking distance to the Green Line station, a 10 minute drive to downtown loop, 15-20 minutes away from Midway Airport, 5 minutes to Lake Michigan, and 5 minutes away from McCormick Place Convention Center, IIT, and Hyde Park/University of Chicago.

Top Guest favourite
A spacious bedroom features a king bed with a memory foam mattress centered against a decorative wall panel. Two potted plants add greenery to the room, with modern pendant lights providing illumination. Large windows allow natural light to fill the space, complemented by a comfortable chair and a mirrored wardrobe.
Apartment in Chicago
4.91 out of 5 average rating, 227 reviews

Lovely 1-bedroom serviced apartment near Museums!

Enjoy Chicago in our modern & spacious 1-bedroom loft in the South Loop. Central location to Grant Park, Soldier Field, Museum Campus, McCormick Place and more! Our location has a walk & transit score of 97, providing easy access to all the hot spots on your itinerary! Expect lovely natural light, luxuriously tall ceilings and room to accommodate your entire group. Guests are always pleasantly surprised by the size of the space and the modern amenities we provide!

Top Guest favourite
A brightly illuminated living area features a light-colored sofa adorned with decorative cushions. A modern coffee table sits centrally, while colorful artwork enhances the walls. The space opens toward a dining area, with a glimpse of the kitchen visible in the background.
Apartment in Chicago
5 out of 5 average rating, 38 reviews

Blake’s Place

Welcome to our charming Air BnB! Nestled in a prime location, this cozy and stylish space is perfect for your getaway. With its tastefully designed interiors, and comfortable furnishings, you'll feel right at home. Our place features plush double queen size bunk beds for a restful sleep, while the fully equipped kitchen allows you to prepare delicious meals. Relax in the inviting living area or step out and enjoy a nice walk along Lake Michigan just 10 mins away.

Top Guest favourite
A cozy living area features a light-colored sofa adorned with a textured throw and a contemporary black-and-white artwork on the wall. A sleek kitchen island with two bar stools sits adjacent to the living space, illuminated by pendant lighting. Large windows provide a view of the outdoor greenery.
Guest suite in Chicago
4.91 out of 5 average rating, 77 reviews

Comfy suite w/ steam shower near McCormick Place

Welcome to the landmark! Our well appointed studio space is situated in the historic Calumet-Giles-Prairie District; minutes from McCormick Place, Sox Park, Wintrust Arena, IIT, and downtown. Walk to 31st St Beach, bike to Museum Campus. Perfect for business or leisure; enjoy steam shower, Wi-Fi, smart TV, and full kitchen. Easy access to major highways and public transit. We also offer a Honda Accord rental car on Turo for your convenience upon inquiry.

Top Guest favourite
Apartment in Chicago
5 out of 5 average rating, 22 reviews

Stylish Hyde Park/Kenwood Brownstone Garden Apt

Enjoy a stylish experience in Chicago's historic Hyde Park/Kenwood neighborhood in this updated brownstone garden apartment. You'll have an entire tastefully designed speakeasy chic 2-bedroom/1.5-bathroom unit with a separate entrance to yourself. Great location off South DuSable Lakeshore Drive- you're minutes away from Lake Michigan's scenic lakefront, the University of Chicago, McCormick Place and downtown Chicago.

Guest favourite
Apartment in Chicago
4.91 out of 5 average rating, 44 reviews

Cozy In the Middle of Everything

Enjoy a stylish experience at this centrally-located place. About a mile from the University of Chicago. 10 Minutes to Downtown Chicago. 3 Blocks from the beach, walking, and bike trails. Near grocery stores and beloved Bronzeville Eateries. Right off Lake Shore Drive with access to all Chicago Expressways. This is the perfect spot to relax while you enjoy all that the City of Chicago has to offer.

Superhost
A modern living area features a curved sofa and two armchairs, arranged around a circular, striped rug. A flat-screen TV is mounted on the wall above a sleek fireplace. Natural light enters through large windows, complementing a dining area with a round table and multiple chairs.
Home in Chicago
4.9 out of 5 average rating, 80 reviews

CasaNova Modern City Living

Sprawling 4 Bedroom, 2.5 Bath 3 story house nestled on private cul de sac in a residential area. Chicago’s North Kenwood/Bronzeville neighborhood walking distance to the lakefront and 10min drive to city’s loop. Features open floor plan with hardwood floors, fireplace in living room, washer dryer, with outdoor space on each floor. Large patio available to enjoy Chicago's city and lake views!

Popular amenities for Oakwood Beach holiday rentals