Vacation rentals in Woodlawn

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

PRIVATE 2-bedroom 1.5 bath w/ living room

Next to University of Chicago campus. Private entry to 2-bedroom/1.5-bath apartment: back half is our separate craft space and front half is your private Airbnb suite. No proper kitchen, but there is a large fridge, microwave, etc. This Airbnb is in our 4-unit apt building next to our house where we've had a 5-star Airbnb room for 10+ years as a Super Host. The other tenants are long-term lease-holders and wonderful people whom we're happy to call our neighbors on this quiet tree-lined street.

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!

Artistic Stay near Hyde Park: 2 Living, Courtyard

Welcome to our newly renovated retreat, Urban Oasis Hyde Park. Embrace the artful decor throughout the spacious house only a 10 minute walk to the nearest beach. Rent a bike for a scenic ride to nearby attractions like University of Chicago, Obama Library, Museums, the Natural Walkway Nature Park and the lake. Conveniently located in Woodlawn, near Hyde Park, central to downtown Chicago, this is the perfect stay for families and friends as you explore everything Chicago has to offer.

University Retreat

Lovely 3 bedroom apartment in Hyde Park location. Within one block of the U of Chicago; close to the science museum, Metra, restaurants, parks, and less than 1 mile from the proposed Obama Library and the lake. Updated unit has nearly 1,300 SF of livable space to enjoy: vintage hardwood floors throughout, separate living/dining rooms, kitchen with new stainless steel appliances, new furnace, new hot water tank, and a new porch with large fenced yard. Permit parking for guests only!

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.

Explore Chicago • Private Parking • Museum Access

Esther & Lily is a historic Chicago bungalow where visitors can relax, work, move, and explore the city. Coming to Chicago for college move-in, campus visit, museums or a fall getaway? Esther & Lily is a home away from home with 3 sleeping spaces, 2 bathrooms, full kitchen, dining, dedicated workspace, multiple sitting areas, a sun room, free street parking, private driveway, self check-in, and garage access. Flexible check in times from now until November 1st.

Modern East Woodlawn Apartment!

Beautiful 2-bedroom, 1-bath modern apartment in the thriving neighborhood of East Woodlawn. Walking distance to the new Obama Presidential Center and University of Chicago. Metra, Green Line, and CTA buses are all just blocks away! Minutes from Downtown Hyde Park and the wonderful lakefront. This unit offers a deck, and private parking. Perfect for a comfortable and convenient stay! Special rates for monthly stays! Reach out for more info!

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.

Lux Modern 3BR on UChicago Campus & Hospitals

Welcome to The Brown House — a bright, spacious 3-bedroom, 2-bath home just minutes from the University of Chicago and major hospitals. Ideal for families visiting students, medical professionals, and groups seeking comfort and convenience. Enjoy fast WiFi, a fully equipped kitchen, in-unit laundry, and easy self check-in. Free street parking is available across the street, with parking passes provided if needed.

Luxe Loft vibe | King Suite |4BR 3Ba

Stay in style near Chicago’s best! This luxe 4BR, 3BA loft is perfect for families, professionals, or UChicago guests. Enjoy a king suite with jacuzzi, 3 queen bedrooms with desks, and an open layout with smart TVs, exposed ducts, and dining for 10. Walk to the Obama Presidential Center, Museum of Science & Industry, and lakefront. Adjacent to Hyde Park with quick downtown transit—just 50 min to Indiana Dunes!

2 BR - 10-Min Walk to Obama Presidential Center

Welcome to your home away from home in Chicago, IL! This spacious 2-bedroom, 2-bath retreat offers the perfect blend of comfort and convenience. Comfortable Living: Bright open living area with cozy seating and smart TV for winding down. Private Bedrooms: Two well-appointed bedrooms with fresh linens Private Bathrooms: No waiting! Enjoy the ease of having two full bathrooms so no one has to wait!