Holiday rentals in Oakwood Beach

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Top-rated holiday rentals in Oakwood Beach

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Guest favourite
A spacious living area features a dark couch adorned with a 'Chicago' pillow. A coffee table sits in front, complemented by modern black chairs. Artwork and decorative elements enhance the neutral-colored walls, while recessed lighting provides a warm ambiance.
Guest suite in Chicago
4.91 out of 5 average rating, 251 reviews

Bike the Lakefront from a Sleek Urban Retreat

Cook in a stainless-steel kitchen with granite countertops, gleaming utensils, and a well-stocked fridge. Black and gray accents and dark woods offset a muted palette at this open-concept home. Thoughtful details include 800-thread-count linens. A retreat designed to evoke relaxation through luxury and elements of the earth. Lush bath linens & robes, luxury body and hair care products, coupled with sleek design creates a spa bathroom retreat you're sure to enjoy. Full granite and stainless steel kitchen, with wine fridge, stocked with morning essentials and Bronzeville BNB staples to ease you into the day's adventure. Relax or be social in the open space living and dining area equipped with Amazon entertainment system and Wi-Fi providing up-to-date weather, sports, news, the latest movies and yes...sometimes...work. Retreat to one of three sleeping accommodations, each drept in 800 thread count, 100% cotton linens. You'll find Bronzeville BNB thoughtful touches around every corner. Enjoy! You'll have access to the full suite including open floor plan living room/dining room/kitchen, spa bathroom, bedroom with walk in closet, hall closet, rear mud room containing washer/dryer, mop/broom, garbage tray, and fire extinguisher. There is concrete patios at the front and the rear entrances also. The backyard, main property deck and garage are restricted areas. The suite is nestled in the historic Bronzeville-Hyde Park neighborhood. Rent a Divvy bike to explore the 18-mile lakefront recreation trail close by. Chicago’s main attractions are a short drive away. The most efficient way to get around the city is UBER offering door-to-door service to all of Chicago's top attractions. Claim your FREE Uber ride (up to $5) gift from the host by signing up using this link: https://www.uber.com/invite/zkyf4 Divvy bike rentals are an awesome way to explore Chicago's 18 mile lakefront trail. The Divvy Explorer Pass includes 24 hours of bike access, with unlimited trips up to 3 hours each for $15/day. Pick up and return bikes at the 575+ Chicago & Evanston Divvy stations. Download the Divvy app for station locations and ride pass purchases. Your safety is important. Please be safe and aware of your surroundings. In any huge city, things can happen. It is suggested to not walk at night, avoid public transportation outside of downtown, and use rideshare transportation apps to avoid exchanging currency.

Top guest favourite
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
4.93 out of 5 average rating, 107 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 favourite
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.
Flat in Chicago
4.92 out of 5 average rating, 153 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.

Top guest favourite
A modern kitchen is depicted with a stainless-steel refrigerator and oven, complemented by a tiled backsplash. Light cabinetry provides ample storage, while a cozy couch with a blue accent pillow offers a welcoming touch. Natural light brightens the space, enhancing the functionality.
Flat in Chicago
4.94 out of 5 average rating, 170 reviews

Cozy 2 bdrm near McCormick Place & Wintrust Arena

Come enjoy Chicago via our cozy apartment in the quiet yet friendly Historical Bronzeville community. We are nestled between Hyde Park and South Loop, where you will find plenty of restaurants, theaters, and nightlife. Only minutes away from McCormick Place, 10-15 min drive from downtown and 3-12 miles from all the sports arenas and airports. You can bike or walk to the nearest grocery store, park, gym, and beach. The nearest bus and/or train is 2-3 blocks away for your convenience as well.

Guest favourite
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.
Guest house in Chicago
4.9 out of 5 average rating, 104 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.

Top guest favourite
The exterior of the building showcases a charming brick façade, featuring a welcoming front door framed by two large, symmetrical windows. A set of stairs leads up to the entrance, which is covered by a small roof overhang. A wrought-iron fence surrounds the entryway.
Guest suite in Chicago
5 out of 5 average rating, 12 reviews

Bronzehaus - near McCormick, UChicago & Downtown

Welcome to Bronzehaus – a chic retreat in the heart of historic Bronzeville. Bronzehaus is a newly renovated, thoughtfully designed 2-bedroom, 1-bath garden-level apartment blending comfort and class. Inspired by the rich jazz legacy and artistic soul of the area, this stylish space features modern amenities and a cozy layout. Whether exploring nearby galleries, museums, a day at the beach, or heading downtown - Bronzehaus offers a comforting stay. Come stay where heritage meets hospitality.

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.
Flat in Chicago
4.93 out of 5 average rating, 45 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!

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, 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.

Guest favourite
A compact bathroom is visible, featuring a shower with a floral curtain, a toilet, and a modern sink with a wooden vanity. Soft neutral tones are present on the walls and floor, complemented by a stylish light fixture above the mirror.
Flat 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.

Guest favourite
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.
Flat in Chicago
4.84 out of 5 average rating, 183 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.....

Guest favourite
A modern living room is presented, featuring a brown leather sofa and two armchairs with light upholstery. A round wooden coffee table sits at the center, accompanied by two textured stools. Two mirrors adorn the wall above the sofa, while large windows allow natural light to fill the space.
Apartment in Chicago
4.96 out of 5 average rating, 47 reviews

The ModernFarmhouse Chicago-Near Downtown Chicago

Welcome to ModernFarmHouseChicago, where we share our soul, heart, and minds with you as we strive to provide you with an unforgettable luxury experience. Whether you’re here to explore downtown Chicago/Lake front just minutes away, or here for the University of Chicago. We hope you absolutely love it here. Naomi & Michael

Guest favourite
The living area showcases a round glass coffee table surrounded by antique armchairs, complemented by a decorative area rug. A mirrored wall reflects natural light, while a pendant light fixture and tiffany lamp provide additional illumination. The kitchen is visible in the background.
Flat in Chicago
4.92 out of 5 average rating, 119 reviews

3bdrm/2bthrm in restored brownstone in Bronzeville

Newly restored Brownstone in historic Bronzeville neighborhood. Built in 1868, this 3br/2ba apartment has antique furniture and finishes with contemporary touches, smart tech & security, in lakefront neighborhood minutes from soldiers field, white sox stadium, the future Obama Library, and downtown Chicago.

Popular amenities for Oakwood Beach holiday rentals

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