Vacation rentals in Oakwood Beach

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Top-rated vacation rentals in Oakwood Beach

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Top guest favorite

A comfortable living area features a dark sectional sofa positioned around a round coffee table. A wall-mounted television is displayed above a modern electric fireplace. Natural light enters through a small window, while a plant and a workspace are subtly included in the room.

Guesthouse in Chicago

5 out of 5 average rating, 20 reviews

Garden Retreat in Historic Bronzeville

Welcome to your home away from home in historic Bronzeville! This private basement unit sleeps 3 with one queen bed and a fold-out couch. Enjoy a full bathroom, private entrance, and everything you need for a comfortable stay. Located near McCormick Place, Chinatown, museums, the lakefront, public transit, and just minutes from downtown. Whether you're here for work or relaxation, we'd be happy to host you! Washer & dryer No chores No dishwasher Early check-in, late check-out if available

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

4.86 out of 5 average rating, 44 reviews

Executive Contemporary Duplex

Discover a newly remodeled, stylish, & spacious 2-bedroom garden home 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, it's perfect for any length of stay.

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, 194 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.

Superhost

The spacious living area features a black sectional sofa, a table with two chairs, and a pool table. Wood-like tiles cover the floor, creating a warm atmosphere. Wall art and photographs complement the minimalist design, while soft lighting enhances the inviting environment.

Condo in Chicago

4.85 out of 5 average rating, 158 reviews

Quiet, Modern, Convenient 2 bedroom condo

PLEASE READ DESCRIPTION PRIOR TO BOOKING* Stay at this quiet, charming, Chicago-themed garden unit, sitting in the heart of Chicago's historic Bronzeville neighborhood. This convenient location with 1000 sq feet of space is perfect for young professionals, student, small groups, families, and people traveling with children. Easy access to public transportation, downtown Chicago, the Museum of Science and Industry, the University of Chicago, downtown Hyde Park, and etc. Hotel style, no kitchen

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.

Guest favorite

The kitchen features dark wood cabinetry and modern stainless steel appliances, creating a functional space. A dining area with a cozy red sofa and art displays is visible, while elegant table settings add a touch of warmth. The multi-functional layout supports relaxation and entertainment.

Home in Chicago

4.91 out of 5 average rating, 43 reviews

Garden Apartment in Gated Home

This large 1300 sq ft professionally decorated, modern apartment has high 14 ft high ceilins and windows that create a bright living atmosphere. It features a fully stocked kitchen with stainless steel appliances. There's lots of entertainment space. It is within 3 miles to downtown, the Convention Center, Solider Field, and White Sox Stadium. Also, Chicago's universities and hospital districts are close by. Walk 2 blocks to enjoy the lakefront and parks. FREE ON SITE PARKING JANUARY- MARCH

A bright living room features a spacious gray sofa adorned with several decorative pillows. A sleek coffee table is positioned in front, with fresh flowers placed on top. Natural light enters through large bay windows, complemented by light shade coverings.

Condo in Chicago

4.93 out of 5 average rating, 27 reviews

Lakeside Retreat: Charming Greystone Near Downtown

Immerse yourself in the vibrant energy of Chicago while enjoying the elegance of our greystone apartment. Located within a 10- 15 minute drive to downtown, you can effortlessly walk or bike to the scenic trails along Lake Michigan/ Lake Shore Drive. This urban oasis offers a perfect blend of city living, providing a comfortable haven after a day of exploring the dynamic surroundings. This location is close to Museums, Aquarium, Planetarium, U of Chicago as well as McCormick Place.

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, 124 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 cozy bedroom features a spacious bed with a soft white comforter. A modern television is mounted on the wall opposite the bed. A circular mirror and small table add to the decor, while a vintage-style refrigerator and a bathroom door are visible in the background.

Private room in Chicago

4.98 out of 5 average rating, 176 reviews

McCormick332, Chinatown, SOX, GrantPark, UC

Feel free to check us other listings: https://www.airbnb.com/h/zengarden001 https://www.airbnb.com/h/zengarden221 https://www.airbnb.com/h/zengarden331 https://www.airbnb.com/h/zengarden333 A new renovated luxury zen garden step to Chicago loop, McCormick Place, Millennium Park, Navy Pier, SOX, Art Institute, UIC, IIT, UCHICAGO, Chinatown(hundreds of delicious food), Midway Airport. Perfect place for everyone in Chicago! Super easy free street parking!

Guest favorite

A private room features a spacious bed with crisp white bedding. A wall-mounted television is situated opposite, with a small table and chair nearby. A fan is positioned to the side, and a compact refrigerator is visible next to the table. Natural light filters through sheer curtains.

Private room in Chicago

4.92 out of 5 average rating, 281 reviews

HydePark002, UC, NavyPier, Chinatown, freeparking

Feel free to check us other listings: https://www.airbnb.com/h/hydepark001 https://www.airbnb.com/h/zengarden333 https://www.airbnb.com/h/zengarden332 https://www.airbnb.com/h/zengarden001 Hyde Park luxury private room with a keypad lock on each room door. Shared full bathroom only for 2 rooms. Step to UChicago, Chicago loop, McCormick, Chinatown(hundreds of delicious food). Perfect for everyone in Chicago! Free street parking.

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

4.96 out of 5 average rating, 23 reviews

Sunny Penthouse - Oakwood Beach

Gorgeous top floor 2 bedroom 2 bathroom condo in Bronzeville. It has high ceilings with lots of natural light. The kitchen is fully equipped with everything you need to cook a delicious meal. Plus, there are many food options nearby. Enjoy a 15 minute walk to the lake front and Oakwood beach. Centrally located near downtown, Solider Field, Rate Field, Field Museum, The Art Institute of Chicago, Chinatown, Hyde Park, and plenty more!

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

4.89 out of 5 average rating, 62 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!