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Vacation rentals in Oakwood Beach

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Top-rated vacation rentals in Oakwood Beach

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

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Top guest favorite
A well-lit bedroom features a spacious bed with a soft, green blanket and burgundy pillows. A wooden desk and chair sit near a closet with sliding doors. Two vibrant artworks adorn the wall, and a cozy area rug adds comfort to the floor.
Guest suite in Chicago
4.92 out of 5 average rating, 106 reviews

Cozy 2BD Lake Apt Near Downtown, McCormick & More

Enjoy your getaway in this cozy solar powered and eco-sustainable garden apartment 5 minutes walking to Lake Michigan where you can access beaches, bike paths, prairies, parks & more! We are less that 8 min away from downtown, the University of Chicago, Soldier Field, the Field Museum and more. Our home is located in the historic Oakland neighborhood, central to so much of what Chicago has to offer. We love welcoming guests to our garden apartment where making your stay relaxing is our pleasure

Guest favorite
A vibrant living area showcases eclectic décor, featuring a colorful mural with artistic motifs on one wall. A round coffee table sits in the center, surrounded by cream-colored sofas adorned with green cushions. A wet bar with wooden stools is visible in the background.
Apartment in Chicago
4.91 out of 5 average rating, 149 reviews

Hidden Gem:Artsy Speakeasy in Historic Bronzeville

Enjoy this fun and unique 1-bed 1.5-bath speakeasy in the heart of Chicago's Bronzeville District. This artsy vibe features eclectic décor, hand-painted murals, Smart TVs, wet bar, wellness studio, remote workspace, free street parking, and ground-level-step-free access. This cozy space is perfect for fun couples, solo adventurers, business travelers, and game night aficionados. Easy access to Downtown (6 miles to Mag Mile, Navy Pier, Millennium Park), Beach (1 mile), Museums, & Sports arenas.

Guest favorite
A multifunctional space is featured with a queen-size Murphy bed tucked into the wall, a mounted television, and a cozy seating area with two armchairs. Natural light is welcomed through the entrance door, and a minimalist design enhances the overall simplicity.
Guesthouse in Chicago
4.9 out of 5 average rating, 101 reviews

Guesthouse | Near public transit and Lake front

A unique 400 sqft loft with bright open concept multipurpose space, large windows, full kitchen, and private access located in the historic Kenwood/Hyde Park area. Public Transportation - 5 minute walk Lakefront - 10 minute walk University of Chicago - 2 miles Museum of Science and Industry - 2.8 miles Mccormick Place 3.4 miles Millennium Park - 6 miles Navy Pier - 6.7 miles Hyde Park restaurants! Perfect for individuals or couples, great access to expressways to get anywhere in the city.

Guest favorite
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
4.95 out of 5 average rating, 40 reviews

Sunny Penthouse - Oakwood Beach

Gorgeous top-floor 2-bedroom, 2-bathroom condo in the heart of Bronzeville! With high ceilings and tons of natural light. The fully equipped kitchen has everything you need to cook a delicious meal, or you can enjoy one of the many great dining options nearby. 🌊Take a 15-minute walk to the lakefront and Oakwood Beach. Centrally located near: • Downtown Chicago • Soldier Field & Guaranteed Rate Field • Field Museum & Art Institute • Chinatown, Hyde Park & Pilsen • And much more!

Guest favorite
A modern living space is illuminated by natural light from large windows, showcasing a stylish dining table accompanied by upholstered chairs. A comfortable seating area features a sectional sofa and decorative accents. A classic game table adds an engaging element to the room's design.
Home in Chicago
4.96 out of 5 average rating, 85 reviews

Oakwood Beach Lake & SkylineViews+CuldeSac+Parking

Modern luxury awaits you in this Urban Oasis in North Kenwood/ McCormick area. New construction with all new finishes and stylish decor. Great natural light, free parking, views of Lake Michigan and the Chicago Skyline, nestled on a culdesac. Take advantage of countless attractions that the Windy City has to offer. A few minutes from Navy Pier, Downtown, White Sox Stadium, Museum Campus, University of Chicago, 31st Street and Oakwood Beach Perfect for photos and filming!

Top guest favorite
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, 136 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 favorite
The exterior of a historic brick home features large arched windows with white shutters. A black wrought-iron fence surrounds the property, adding charm. The main entrance is accentuated by a dark door and stone steps lined with planters, contributing to the building's classic architectural style.
Guest suite in Chicago
4.95 out of 5 average rating, 212 reviews

Bronzeville Beauty: Modern Style + Historic Charm

Come relax and take in Chicago's historic Bronzeville neighborhood. Stay in the bright and sunny garden unit of a fully renovated landmarked home built in 1887. We are located across from a neighborhood park with excellent access to CTA transit. Walkable to Lake Michigan, Lakefront Trail, White Sox stadium, IIT. Very close to McCormick Place, Hyde Park, and Chinatown. If you drive, free street parking is readily available in front of our home.

Top guest favorite
A cozy living area features a modern gray sofa adorned with yellow pillows, situated on a patterned rug. A low wooden media console holds a flat-screen TV, while large windows allow natural light to brighten the space. Colorful artwork is displayed on the walls.
Home in Chicago
4.96 out of 5 average rating, 266 reviews

Peaceful Modern Full House in Trendy Bridgeport

Kick back & relax in your home away from home in our modern & peaceful space in the heart of the Bridgeport neighborhood. Featuring incredible natural light, modern amenities & beautiful artwork, the house is impeccably clean and designed to ensure you have the best travel experience possible. Located on popular Morgan Street, you're only blocks away from bakeries, farm-to-table restaurants, independent coffee shops and local breweries.

Guest favorite
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, 70 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!

Guest favorite
A cozy front room features a light gray sofa adorned with decorative cushions. A sleek glass table is positioned beside the sofa, while a large wall-mounted TV is visible above. Natural light enters through a small window with blinds, and a colorful area rug adds warmth to the space.
Apartment in Chicago
4.93 out of 5 average rating, 43 reviews

Comfy Near Downtown Chicago

Keep it simple at this peaceful and centrally-located place. Near the University of Chicago and only ten minutes from Downtown Chicago. Located in the Bronzeville neighborhood on a cute and quiet block. Spacious one bedroom unit with a newly remodeled bathroom and Jacuzzi tub. Big screen TV in the cozy and comfy front room. And nice kitchen with the setup ready for meals and entertainment.

Top guest favorite
A cozy sleeping area features a queen bed adorned with plush yellow pillows atop crisp white linens. A vibrant mural in earthy tones of green, pink, and orange adds a modern touch to the room, complemented by natural light from the nearby window.
Apartment in Chicago
5 out of 5 average rating, 35 reviews

2BR Brownstone 7-min to Events, Downtown, & Lake

Welcome to The Garden Oasis — a cozy, winter-ready Chicago retreat just 5 minutes from Soldier Field and McCormick Place. Perfect for Bears games, conventions, and stay-in nights, this historic brownstone features a warm living space for movies, board games, and hot chocolate with marshmallows. Close to great food and downtown, yet ideal for relaxing indoors after a day out.

Guest favorite
A modern living area features a light green sectional sofa adorned with dark blue accent pillows. A decorative area rug with a subtle pattern is positioned beneath a glass coffee table. Natural light filters through sheer curtains, and a plant adds a touch of greenery.
Apartment in Chicago
4.83 out of 5 average rating, 181 reviews

The Posh Apt. Mins to Downtown & Hyde Park

This spacious garden apt in a 12 yrs old building is sitting in the heart of a historical Bronzeville neighborhood. The unit is setup with all necessary amenities/supplies that will make you comfortable and a memorable trip for you. It is modern, contemporary and a most stay place for a guest like you! I bet you will like it.....

Popular amenities for Oakwood Beach vacation rentals

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Chicago
  6. Oakwood Beach