Holiday rentals in Washington Park

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

Amazing historic campus mansion!

This stylish campus mini mansion is perfect for group trips in the historic Hyde Park neighborhood. A cheerful, modern renovation of a historic home, with original woodwork, underfloor bathroom heating and leaded windows. Easy access to Uchicago, the lakefront, Chicago marathon, McCormick trade shows, the Museum of Science & Industry or exploring our vibrant city. Our spotlessly clean property helps you experience everything Chicago has to offer. Hosted by a very experienced all 5 star host.

Sunny Penthouse - Oakwood Beach

Bright top-floor 2-bedroom, 2-bath condo in the heart of Bronzeville with soaring ceilings and abundant natural light. Relax in the in-unit jacuzzi jetted tub after a day exploring Chicago. The fully equipped kitchen has everything you need to cook at home, or enjoy nearby restaurants. 🌊 Just a 18-minute walk to Oakwood Beach & the lakefront. Within a 20-minute drive of Downtown, Soldier Field, Guaranteed Rate Field, the Field Museum, the Art Institute, Chinatown, Hyde Park, Pilsen & more!

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.

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.

3BR • 5 Min to UChicago • 15 min to Downtown

Make this spacious 3BR condo your cozy Chicago home base this fall and winter, just 15 minutes from downtown in a relaxed residential area. Settle into two King bedrooms and one Queen, stretch out on the roomy sectional, and enjoy thoughtfully chosen art throughout. Cook a comforting meal in the stocked kitchen, cozy up for movie night, or unwind with the PS5. With a dedicated desk and plenty of room to spread out, it’s a warm, comfortable stay for families, groups, and professionals.

Stylish Flat near Downtown,Obama Library, UChicago

Stylish Luxury Retreat in Woodlawn | Near the Obama Presidential Center, Downtown & UChicago. Experience modern comfort and style in this beautifully space nestled in the vibrant community of Chicago. Features two beautifully designed bedrooms , luxurious bathroom, and an open living and dining area perfect for relaxing. Prepare your favorite meals in the upscale, fully equipped kitchen, then unwind on the private balcony with your morning coffee or evening glass of wine.

UChicago Condo | 2 Baths, Private Parking & Entry

Enjoy the convenience of a dedicated private parking space with direct access to your own private entrance. This upgraded and spacious 1-bedroom, 2-bathroom condo near the University of Chicago features hardwood floors, stainless steel appliances, in-unit laundry, two Smart TVs, a cozy reading nook, and a large outdoor patio. Conveniently located near Hyde Park, Lake Michigan, Jackson Park, and the Obama Presidential Center. Perfect for extended stays and remote work.

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.

Cozy Retreat in Hyde Park | In Unit Laundry

There are about 5 steps that you have to go down to get to the apartment. This beautifully designed apartment features exposed brick walls, modern furnishings, an open-concept layout, and a fully equipped kitchen, blending comfort and character. Relax in the bright living space or explore nearby restaurants, museums, lakefront parks, and the University of Chicago. Perfect for couples, business travelers, and healthcare workers.

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.