Holiday rentals in Washington Park

3BR • Massage Chair • 5 Min to UChicago • Sleeps 6

This inviting retreat is just minutes from the University of Chicago and only 15 minutes from downtown. Unwind in the massage chair, stream your favorite shows, or settle into a clean, modern space with updated furnishings, a remodeled bathroom, full kitchen, and in-unit washer and dryer. With 3 private bedrooms and everyday conveniences that make longer visits easier, it’s a great home base for work trips, extended UChicago stays, medical travel, or simply spending more time exploring Chicago.

Luxury 4BR w/ Spa Tub Near UChicago & Obama Center

Discover Metra Haven, a luxury thoughtfully designed 4BR near Hyde Park, this home is ideal for bachelorette weekends, girls trips, family gatherings, professionals or large groups seeking cozy comfort Unwind in the spa-style bath tub, gather in the private backyard patio, with fire place for cozy evenings accommodating your group Steps from Metra station with a direct train to Downtown, 4mins away from the Obama presidential center in Jackson pack, museum of science & industry and the lake

Modern Soul Retreat: 3BR in Bronzeville/HydePark

Experience a modern sanctuary where design meets history in the heart of Chicago’s legendary Bronzeville. This spacious 3-bd, 2-ba flat blends art, minimalist comfort, and cultural warmth. Steps from Hyde Park, Lake Michigan, and local cafes, the space invites you to unwind, reflect, and reconnect with the soul of the South Side. Featuring curated decor, luxury finishes, and a nod to Bronzeville’s Soulful Metropolis legacy, this home offers a one-of-a-kind stay—equal parts style and heritage.

Garfield Greystone - 10 Mins to Obama Ctr & Dwtn

Enjoy a beautiful three-bedroom, two-bathroom apartment in a vintage greystone located in Washington Park with designer finishes. Just a 3-minute ride to The University of Chicago Hospital and campus. The unit is a short drive to Chicago’s lakefront. Just a 10-minute ride from The Obama Center, McCormick Place, Soldier Field, with easy access to downtown Chicago. This unit was remodeled and crafted especially with our guests in mind. The unit is suited for solo traveler and families alike.

Quaint 3BR Home Near Attractions

Welcome to our cozy 3-bedroom apartment on Chicago's vibrant south side! Perfectly located near trains and buses, this charming space offers convenience and comfort. Explore nearby attractions, enjoy local cuisine, or relax in our thoughtfully furnished home-away-from-home. Ideal for families or groups seeking a memorable stay in the heart of the city. It is located on a quiet street, with quick access to buses, L Trains, freeways, and a shopping plaza. Walking distance from XS Tennis.

Spacious Parkside 3BR Retreat

Stay just minutes from the Obama Presidential Center! This inviting 3-bedroom, 2.5-bath home is perfect to relax while exploring Chicago. One reserved parking space is included, and monthly stays are welcome. Nearby attractions include: * Obama Presidential Center * Historic Hyde Park * University of Chicago * Museum of Science and Industry * Lake Michigan Beaches * South Loop * Downtown (Mag Mile, Navy Pier etc.) * Chinatown Perfect for families, groups & business travelers.

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.

Hyde Park 5 Bed/3 Full Bath Condo- Travelers Only!

This will likely be the largest condo you have ever seen. This condo is 5 mins from the University of Chicago and the University of Chicago hospital. You will be a quick 10-15 min uber ride from downtown and 5 mins from beautiful Lake Michigan. We are currently only booking out of town travelers. We are not doing parties or events. I live in the building so if you are trying to have a party I will have it shut down and you will be asked to leave within an hour.

Washington Estate minutes from University of CHI

Kick back and relax in this calm, stylish space. The Washington Estate is the professional escape. We provide a 1-bed/2-bath to accommodate a maximum of two guests. Everything you need, full kitchen, WIFI, exercise room, in unit laundry and exterior patio seating for your enjoyment. Gated parking available upon request. Near the historic Hyde Park, the University of Chicago and 8 minutes away from Lake Shore Drive. Walking distance from public transportation.

Stylish Hyde Park/Kenwood Brownstone Garden Apt

Enjoy a stylish experience in Chicago's historic Hyde Park/Kenwood neighborhood in this updated brownstone garden apartment. You'll have an entire tastefully designed speakeasy chic 2-bedroom/1.5-bathroom unit with a separate entrance to yourself. Great location off South DuSable Lakeshore Drive- you're minutes away from Lake Michigan's scenic lakefront, the University of Chicago, McCormick Place and downtown Chicago.

Modern Eco Stay • UChicago • Parking • Backyard

Relax in this eco-friendly South Side retreat designed for comfort, style, and convenience. Located minutes from UChicago, Hyde Park, Jackson Park, the Museum of Science & Industry, and the lakefront, this unit is perfect for families, medical visits, students, and anyone exploring Chicago. With a private entrance, free parking, and a large fenced backyard, this modern space gives you privacy and peace in the city.

Spacious 3BDR Luxury Penthouse

Stylish 3BD/2BA penthouse with high ceilings, oversized windows, stainless steel appliances, quartz countertops, in-unit laundry, and parking. Located in Bronzeville, just 10 mins to downtown, 8 mins to the University of Chicago, 18 mins to Soldier Field, and 25 mins to Midway Airport. Perfect for families or groups seeking comfort, convenience, and a premium city stay.