Holiday rentals in Woodlawn

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.

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.

You are my Muse!

Allow the Muse to be your home away from home. It provides luxury and comfort. Its unique decor was chosen with you in mind. The Muse is filled with energy that captures your artistic eye. Each room tells a story. Each piece was carefully selected. It sleeps 4-6 and has space to entertain. The Muse is nestled in the heart of Woodlawn. The expansive unit, has one full and two half baths. Each has a spa-like feel; especially the full bath that is easily accessible through the masons.

Historic Spacious Chicago Home • Free Parking

Esther & Lily is a historic Chicago bungalow where visitors can relax, work, and explore the city. A home away from home, this Guest Favorite features 3 sleeping spaces, a dedicated workspace, dining room, multiple sitting areas, a fully equipped kitchen, free parking, and self check-in. Conveniently located near Hyde Park, the University of Chicago, museums, the lakefront, the Obama Presidential Library, and downtown, Esther's Abode is the perfect home base for your stay.

Designer Stay in Hyde Park: 2 LivingRms, 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 near Hyde Park central to downtown Chicago, this is the perfect stay for families and friends as you explore everything Chicago has to offer.

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.

Beautiful Penthouse (Near Obama Center, UChicago)

This is 3BR/2B condo located in Woodlawn on the confluence of Hyde Park, walking distance to the University of Chicago and a 15 min drive from downtown! The condo includes modern and new appliances, fireplace, In-unit washer/dryer, walk-in closet, double vanities in bathrooms, and a rear deck. Couch is also a pull-out bed for living accommodations. One designated parking space is available for Airbnb guests, with free street parking also available.

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.

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!

A Stones Throw from U Chicago South Campus!

This spacious 2 bedroom garden unit is located in a lovely renovated vintage World's Columbian Exposition-era graystone. Located across the street from the University of Chicago campus, this comfortable and quiet unit is also within walking distance of the Obama Presidential Center, lakefront beaches, golf courses, the Museum of Science and Industry, public transportation, and Jackson Park. No pets allowed.

South Shore Oasis | Lakefront Suite Near Hyde Park

Thoughtfully renovated garden-level guest suite with private entrance in Chicago’s historic South Shore, just outside Hyde Park. Ideal for visitors to the University of Chicago, Jackson Park, the Obama Presidential Center, and the lakefront. A peaceful home base with easy access to public transit and downtown. Perfect for guests visiting family, attending local events, or exploring Chicago’s South Side.