Holiday rentals in South Side

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Top-rated holiday rentals in South Side

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Guest favourite

Guest suite in Chicago

4.91 out of 5 average rating, 229 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.

Guest favourite

Guest house in Chicago

4.92 out of 5 average rating, 76 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 favourite

Home in Chicago

5 out of 5 average rating, 9 reviews

Mini-mansion Bronzeville!

The whole group will be comfortable in this spacious and unique space. With generously sized rooms and two and a half bathrooms, there’s plenty of space for families, groups, tea parties or just a cozy getaway with friends. Each room tells a story, original woodwork that whispers charm of a bygone era. Explore the original craftsmanship of Chicago reflected in our stunning staircase, the proud centerpiece of the home, inviting you to the second and third floors where comfort meets character.

Superhost

Flat in Chicago

4.67 out of 5 average rating, 33 reviews

VlP STUDlO - 3rd FLr

Welcome to our 3rd FLOOR VIP STUDIO!!! Located on the 3rd FLOOR of our charming older building. Designed to provide you the optimal comfort and relaxation after your long day. We realize, we’re not a hotel, ergo we may not be a good fit for all; HOWEVER; :) as you decide to try us out, you will not be disappointed you did!! We’re always available to you, our aim; to leave you happier and more refreshed than when you came. AND OF COURSE OUR REPEAT GUESTS GET AN EXTRA 8% OFF WHEN THEY RETURN!

Top guest favourite

Flat in Chicago

5 out of 5 average rating, 10 reviews

Entire Penthouse Unit in Chicago

Step into luxury with our newly constructed, entire condo located in the heart of the vibrant Bronzeville Art District. Situated in a gated building within a quiet neighborhood, this 3rd floor penthouse 3-bedroom, 2-bath luxury condo provides the perfect place to unwind after busy days of sightseeing or working remotely. Hardwood floors, custom kitchen with new appliances, bespoke bathrooms, in-unit laundry, and video intercom. Yemi is a super host, check out profile for other listings.

Guest favourite

Flat in Chicago

4.93 out of 5 average rating, 116 reviews

Spacious 1BR Garden Apt & Parking

Welcome to our tranquil garden apartment on a quiet residential street near the university and all Hyde Park attractions. Enjoy morning light through picture windows in the spacious living room and adjacent kitchenette. Breakfast on the patio or garden bench on a sunny morning. Stroll to one of 20+ eateries within four blocks. We are on-premises hosts and owners, available for whatever may arise. Access is private via back gate just off the parking lot with reserved parking space.

Guest favourite

Apartment in Chicago

4.92 out of 5 average rating, 169 reviews

Ultra clean/cozy condo, 10 mins south of Downtown!

The space has been intentionally designed to offer a modern, yet comfortable feel for individual guests or families. Conveniently located just 6 miles south of Magnificent Mile, 5.6 miles from Navy Pier, 1 mile to Lake Shore Drive, 1.5 miles from the University of Chicago, 2 miles from Museum of Science and Industry, 1.2 miles from the many restaurants on 53rd Street in Hyde Park and close to many Chicago favorites! On-street parking available directly in front of the building.

Guest favourite

Flat in Chicago

4.92 out of 5 average rating, 76 reviews

Comfy Solar & Green 2BR Near Hot Hyde Park!

Hi, traveler! We're so happy to host you in our unique, private 2-bedroom garden unit that's powered by the sun. It's all electric, uses no gas and is U.S. DOE Zero Energy and Energy Star® certified! You'll also have a full kitchen, full bathroom/shower, washer/dryer, living room, work area, generous closet space, and complete privacy. Your children are also welcome. We're centrally located on a quiet, residential street in safe and lovely Woodlawn near hot Hyde Park!

Guest favourite

Loft in Chicago

4.99 out of 5 average rating, 111 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

Guest suite in Chicago

4.93 out of 5 average rating, 46 reviews

Classic Den @ U Chicago

Our homey space includes full bath, kitchenette, living area and super comfy Queen bed. Direct access to unit from the exterior rear door makes coming and going easy. Located on University Ave. just a minutes walk to U. Chicago campus, easy access to public transportation taking you downtown in just over half an hour. *Note*This is in the basement of our home. Interior stair door locks from basement side to ensure guest privacy. You will hear us upstairs at times.

Guest favourite

Home in Chicago

5 out of 5 average rating, 11 reviews

The Modern Muse of Chicago! Close to everything!

Newly remodeled home. Art, luxury, and location!!! Enjoy a luxurious stay in this stunning 3-bedroom, 2.5-bath greystone near Chicago's top attractions. Basement unit of the home is separate and it is occupied. Relax in the king-size primary suite, work in the dedicated office, and enjoy two outdoor spaces. Street parking is free, and garage access is available. Perfect for those seeking a blend of comfort and convenience in the city!

Top guest favourite

Flat in Chicago

5 out of 5 average rating, 5 reviews

Zen's ~ Quiet, Near Beach/Golf, DT, 1425 sq ft

Discover this renovated historical Chicago bungalow nestled in the cultural South Shore neighborhood. ~ Michelle Obama's childhood home and school are nearby ~ The block is the origin of the Back Alley Jazz community festival ~ Museum of Science & Industry ~ Garden of the Phoenix ~ Nature trails & Beaches ~ Jackson Park Golf Course ~ South Shore Cultural Center ~ Nearby access to bus/train, beaches, and free street parking