Vacation rentals in Washington Park

4.75 out of 5 average rating, 67 reviews

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.

4.91 out of 5 average rating, 33 reviews

Home in South Side

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

5.0 out of 5 average rating, 28 reviews

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.

4.87 out of 5 average rating, 15 reviews

Near UChicago, 3BR Apt, Parking, W/D, 2 Workspaces

Work-ready 3BR, 2BA apartment located just minutes from UChicago and several major hospitals. Once inside, everything is on one floor. Sleep well with a king, queen, and full bed, plus two full tub/shower baths. Set up at 2 dedicated workspaces with fast WiFi. Cook in a stocked kitchen with full-size stainless appliances, a dishwasher, a coffeemaker, kettle, and other basics. Private in-unit stackable washer/dryer. Free street parking usually nearby. Great for professionals and longer stays.

A bright corner of the room features two soft, light blue chairs positioned around a small circular table. Sheer gray and white curtains frame the windows, allowing natural light to fill the space. A modern floor lamp stands beside the table, enhancing the cozy atmosphere.

4.74 out of 5 average rating, 39 reviews

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.

A spacious living area is furnished with a sleek, grey sectional sofa featuring an orange accent pillow. Clear floor tiles extend throughout the room, leading to a nearby kitchenette and dining area. Soft lighting enhances the welcoming atmosphere, with windows allowing natural light to filter in.

4.86 out of 5 average rating, 42 reviews

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.

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 South Side

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.

4.99 out of 5 average rating, 156 reviews

Top guest favorite

A spacious living area is furnished with two comfortable sofas and an armchair. A central coffee table rests on polished wooden floors. A built-in bookshelf displays decorative items, and a fireplace adds character, complemented by a wall-mounted television above.

Apartment in Hyde Park

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.

4.94 out of 5 average rating, 582 reviews

A modern kitchen features white cabinetry and stainless steel appliances, including a refrigerator and microwave. A marble countertop extends to a bar area with three red stools. Decorative elements, including a vase of flowers, enhance the inviting atmosphere.

4.87 out of 5 average rating, 89 reviews

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.

5.0 out of 5 average rating, 28 reviews

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.

4.98 out of 5 average rating, 49 reviews

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.