Holiday houses in South Side

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Top-rated holiday rentals in South Side

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Guest suite in Chicago

4.91 out of 5 average rating, 227 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

Private room in Chicago

4.96 out of 5 average rating, 111 reviews

Gracious home, superb location

Tucked inside the condo's front door for easy access/egress, large bedroom with queen-sized bed, bath en-suite that offers lovely natural light and a screen of trees. Bedroom opens to a lovely private balcony, perfect for morning coffee and take out meals. Minutes from Lake Michigan, Hyde Park restaurants, UChicago, museums, bike trails & a 10 - 15 min ride on express transit to downtown. Divvy bikes nearby. We have 2 sweet dogs and a lovely, aloof cat. Please note our home is on the 3rd floor.

Superhost

Private room in Oak Park

4.73 out of 5 average rating, 298 reviews

Little Gem Double Rm Home Base for Chicago Trips!

Great home base for Chicago adventures & PREMIUM location in the epicenter of Oak Park - America's home of prairie architecture! Beautiful park/Frank Lloyd Wright homes are directly outside your door and you are only a 25-minute train ride to Millennium Park & all of Chicago! Eclectic garden level (shared) apartment decorated with fun and funky furnishings. Private Bedroom with new double size bed, deluxe bedding, towels. Shared bathroom, living room, and kitchenette. View my other 2 listings!

Guest favourite

Private room in Chicago

5 out of 5 average rating, 14 reviews

The Champlain Suite

This unique place has a style all its own. Bronzeville is a center for African-American life and culture in Chicago. Historically known as the city’s “Black Metropolis,” Bronzeville has a strong sense of pride in its influential history and cultural scene. Spend the night in a home that reflects Bronzeville Art Culture. Rest and relax in a well appointed condo that feels like a home. I am a past Super Host. This room have a Private Bathroom off the bedroom and is not shared with other guest.

Guest favourite

Condo in Chicago

4.92 out of 5 average rating, 166 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

Loft in Chicago

4.99 out of 5 average rating, 109 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

Private room in Chicago

4.93 out of 5 average rating, 175 reviews

Private Unit001, McCormick,Chinatown,SOX,GrantPark

Feel free to check us other listings: https://www.airbnb.com/h/zengarden221 https://www.airbnb.com/h/zengarden331 https://www.airbnb.com/h/zengarden332 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 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.

Top Guest favourite

Private room in Chicago

5 out of 5 average rating, 30 reviews

Lower Level Oasis - Bed, Bath & Living Rooms

My name is Ebony and my husband's name is Ean. We live in Woodlawn with our newborn baby and our cat. We live in a modern home that we try to make comfortable for guest. It has a fair amount of space and is close to the University of Chicago and public transit on the Greenline. This room is in the basement and has a bathroom next-door to it. What makes the listing unique is a shared space with a couch, TV and a Peloton / treadmill. We all use the same entrance.

Guest favourite

Private room in Chicago

4.92 out of 5 average rating, 273 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 favourite

Apartment in Chicago

5 out of 5 average rating, 6 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!

Apartment in Chicago

4.67 out of 5 average rating, 3 reviews

Sunny Studio by UChicago, Walk to Campus & Museums

Cozy, sunlit studio in the heart of Hyde Park. Just blocks from UChicago! Enjoy a comfy queen bed, fast Wi-Fi, private bath, and a fully stocked kitchen with all the essentials. Located on a quiet, tree-lined street in one of the safest, most walkable areas. Steps from cafes, restaurants, parks, and museums. Easy access to CTA/Metra for trips downtown. Perfect for solo travelers, couples, and visiting academics!