Vacation rentals in Oakwood Beach

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Top-rated vacation rentals in Oakwood Beach

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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

4.92 out of 5 average rating, 136 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

Home in Chicago

4.83 out of 5 average rating, 6 reviews

Bronzeville 42: Art & Hospitality Mins to Downtown

Bronzville 42 (B42) is a vibrant space where art meets hospitality! Featuring captivating artwork from the owner's collection, B42 is beautifully decorated and conveniently located just 12 minutes from Downtown and minutes to Hyde Park, the lakefront beach, and the upcoming Obama Presidential Center (opening spring 2026). Dining: - Table seats 6 - Kitchen seats 4 Accommodations: - Sleeps 8 Bedrooms: 1. BR1: King bed 2. BR2: 2 Twin beds 3. BR3: 2 Queen beds Bathrooms: 2 Full Bathrooms

Superhost

An open-concept kitchen and living area features a modern design, highlighted by sleek cabinetry and a spacious island with seating. Natural light fills the room, accentuating the contemporary fixtures and appliances. A comfortable couch is positioned in the inviting living space, creating a perfect gathering spot.

Home in Chicago

4.87 out of 5 average rating, 45 reviews

Executive Contemporary Duplex

Discover a newly remodeled, stylish, & spacious 2-bedroom garden home with a separated basement apartment nestled in the historic Bronzeville neighborhood. This beautiful residence boasts enchanting décor and well-appointed living spaces that promise a memorable stay. Its minimalist charm and comfortable setup reflect a contemporary/modern aesthetic, making it an irresistible choice for guest. Just 6 mints from the downtown, 20 mints from Midway Airport, and 4 mints from McCormick Place & UOC.

Guest favorite

A well-maintained outside space features a neatly trimmed grassy area along a pathway, flanked by vibrant greenery and flowering plants. On one side, a wooden deck with railings enhances the exterior of the two-story building, while a fence provides privacy.

Apartment in Chicago

4.9 out of 5 average rating, 198 reviews

Royal Coach House Cottage

Royal Coach House Cottage- Nestled in Bronzeville community and nearby Historic Hyde Park neighborhood that is safe and family oriented. Our space is quite cozy, quaint and ideal for relaxation, peace & quiet. Flower and vegetation garden landscape. Centrally located 1.5 miles from lake front, nearby shopping, movie theater, and restaurants. Seconds from park, walking track and playground. Minutes from downtown and Magnificent Mile. Local transportation accessible including bicycle rental.

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

4.89 out of 5 average rating, 91 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.

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

4.68 out of 5 average rating, 31 reviews

Cozy Uneek Space - Centrally Located Garden Unit

Need a cozy, unique, convenient, & affordable place to stay? Look no further! This might just 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 perfect escape. Relax, rejuvenate, & leave your worries behind in this space designed for your comfort & convenience.

Top guest favorite

A striking two-story black house is framed by lush greenery and well-maintained shrubs. The inviting front porch features wooden steps leading to a black door with decorative trim. Large windows are present, allowing for ample natural light, and a fence encircles the property.

Home in Chicago

5 out of 5 average rating, 30 reviews

Villa Noir Chicago Victorian 7 min to downtown

Welcome to Villa Noir - an expertly designed vacation HOME fully equipped with everything you need for a most enjoyable stay! Our home features 4 spacious bedrooms, 2.5 bathrooms, dedicated workspaces and a chef’s dream kitchen…not to mention an entire level of entertainment space! Complimentary amenities throughout…high-speed Internet, smart TVs, and coffee station. We are centrally located…a 7 minute drive to downtown dining / shopping, museums, the beach, McCormick Place and more!

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, 24 reviews

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

Welcome to The Garden Oasis! Stay here if you want to live like a local in a historic Chicago Brownstone just minutes from the heart of the city. Thoughtfully designed with modern touches, a cozy living space, and plenty of natural light, it's the perfect place to relax after exploring. Walk to the beach, lakefront trail, and local eateries, or take a quick ride downtown to visit Chicago’s top attractions. Experience the best of the city from your own private retreat!

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, 126 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.

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, 83 reviews

NEW! Lake & Skyline Views Kenwood CuldeSac+Parking

Modern luxury awaits you in this Urban Oasis. 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!

Guest favorite

A modern multi-story building is showcased, featuring a textured brick facade and large windows. A well-maintained green space with bushes and grass is positioned in front, complemented by a black iron fence that outlines the property.

Condo in Chicago

5 out of 5 average rating, 24 reviews

Bronzeville Oasis

Kick back and relax in this calm, stylish space in the heart of Chicago’s legendary Bronzeville neighborhood. This stylish condo is minutes away from downtown Chicago, the magnificent mile, Navy Pier, Lakeshore Drive, the University of Chicago, and the museum of Science and Industry. You can also enjoy many restaurants in the heart of Hyde Park minutes away on 53rd St. On street parking is available directly in front and beside the building.

Superhost

A living area features two sofas and a coffee table centered on a colorful area rug. Warm lighting emanates from two table lamps beside the sofas. Artwork adorns the wall, enhancing the cozy ambiance of the space.

Place to stay in Chicago

4.89 out of 5 average rating, 27 reviews

Large Studio Apartment with no cleaning fee

Large studio garden unit located in the lowest level of a 3 level home. Space is private with no shared interior common area. Great location. Minutes from Lake Michigan trails and beaches. City bus is close and El (train) 1 mile to west. 8 Minutes to Grant Park and all the city has to offer. Mccormick Place and University of Chicago are about 5 Minutes. Always plenty of street parking. Uber and Lyft serves.