Apartment holiday rentals in Woodlawn, Chicago

Royal Coach House Cottage

Royal Coach House Cottage- Nestled in Bronzeville community and nearby Historic Hyde Park neighborhood that is safe and family oriented. Our space is quite cozy, quaint and ideal for relaxation, peace & quiet. Flower and vegetation garden landscape. Centrally located 1.5 miles from lake front, nearby shopping, movie theater, and restaurants. Seconds from park, walking track and playground. Minutes from downtown and Magnificent Mile. Local transportation accessible including bicycle rental.

Charming 2-bdrm near University of CHI Campus

Perfect for business travelers, healthcare professionals, and U of C affiliates, this newly renovated and fully furnished 2-bedroom, 1-bath apartment offers comfort and convenience. Located on a peaceful, tree-lined street in the vibrant Woodlawn/Hyde Park neighborhood, the unit features modern amenities including an in-unit washer and dryer, high-speed Wi-Fi, and a dedicated workspace. Public transportation (Metra + CTA) is just steps away and downtown Chicago in just 15 minutes by car.

Cozy Studio Apt. Home-5 Min. to U of C

A private guest suite 5 min. from UChicago campus. Full access via private entrance to cozy studio created in bsmt of our home. An open floor plan with louvered wooden doors close off bedroom w/dbl bed. A full kitchen, ceramic tile bath w/tub, hand-held shower head+vanity mirror. Studio guest: "Your place really stands out from all the landlord-managed airbnb stuff in Hyde Park!" Five min. to campus, fitness ctr, & CourtTheatre; convenient, cozy & private. Registration #R24000123950

Quaint Apt near UChicago, Wifi + Parking + Laundry

Unwind at our stylish and cozy 3-bedroom, 2-bathroom apartment located just steps from the University of Chicago in the vibrant Woodlawn neighborhood. The space features, an open-floor plan, hardwood floors, a fully equipped kitchen, plenty of natural light. It's the perfect place for a family or a group of friends who want a quiet place to relax while still being close to food, fun and tourism in Chicago. Ideal for family vacations, group trips, traveling professionals or students.

Spacious 1BR Garden Apt & Parking

Welcome to our tranquil garden apartment on a quiet residential street near the university and all Hyde Park attractions. Enjoy morning light through picture windows in the spacious living room and adjacent kitchenette. Breakfast on the patio or garden bench on a sunny morning. Stroll to one of 20+ eateries within four blocks. We are on-premises hosts and owners, available for whatever may arise. Access is private via back gate just off the parking lot with reserved parking space.

Best Location in Hyde Park apartment

Lovely 2 bedroom apartment in Hyde Park location. Within one block of the U of Chicago. The lake is within a 10min walk. Close to the science museum, Metra, restaurants, parks, and famous Japanese garden. Updated unit was remodeled last year for you to enjoy. Separate living/dining rooms. The dinning room has a large table for you to enjoy a meal or get some work done. Great view to the park and tennis courts and porch on the kitchen to enjoy breakfast outside. Parking available.

Beautiful European Apartment

Enjoy this comfortable 1600 sf European Styled 3 bedroom (Queen Beds in each room) 1 bath apartment with lots of natural light. Formal dining room,comfortable living room with attached sunroom. Quite neighborhood and 3 blocks away from Public “Elevated Train” line and “Buses” to anywhere in Chicago. The apartment is walking distance from University of Chicago and the beautiful Washington Park. The park has wonderful Walking/Running Paths and Pool (Seasonal).

Modern Apt with style & comfort in Pilsen Chicago

Enjoy a nicely updated studio in a safe, family-owned building located in Pilsen/Heart of Chicago conveniently located near Downtown, Chinatown, & Hyde Park to name a few. Public transportation is walking distance or you can go on a short drive to museums, parks, cafes, restaurants, bars, venues, and hip neighborhoods. Chicago has a full line up of festivals happening this year so feel confident in choosing my lovely space to be part of your experience.

Beautiful 3BR/2BA Penthouse

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.