Vacation rentals in Woodlawn

4.9 out of 5 average rating, 30 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

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4.96 out of 5 average rating, 70 reviews

A spacious living area features high ceilings with a skylight and large windows, offering ample natural light. A comfortable green sofa and a black armchair are positioned near a coffee table. A fireplace and a television are visible, with scenic views seen through the glass doors.

Apartment in South Side

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!

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Guest suite in South Side

4.91 out of 5 average rating, 124 reviews

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.

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4.69 out of 5 average rating, 55 reviews

A two-story cottage is displayed with a front porch featuring white railings. Well-maintained shrubs line the pathway to the entrance. The exterior is clad in light-colored siding, and large windows allow natural light to brighten the living spaces inside.

Home in South Side

Cozy Chicago Cottage

Relax with the whole family at this peaceful cottage located 3 blocks away from the University of Chicago on a quiet cul-de-sac. This gated home boasts 3 bedrooms, a full kitchen and 1.5 bathrooms. After a beautiful Chicago day, return to your space and enjoy free wifi, a movie, streaming service or a great conversation while resting on the front porch. Staying for an extended time? No worries, you may launder your belongings on site. Also, there is plenty of free residential parking!

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4.82 out of 5 average rating, 33 reviews

A cozy living area is highlighted by a purple sofa, adorned with decorative cushions. A tall potted plant is situated nearby, adding a touch of greenery. Natural light filters through three large windows, creating a bright and inviting atmosphere. A glass coffee table occupies the center of the space.

Apartment in South Side

Vintage Ambience

Take it easy at this unique and tranquil vintage home. Two bedroom 1 bath, full kitchen, formal living and dining room, enclosed back porch filled with quiet, peaceful escape opportunities. There is a creative multi purpose space for those of you who must continue to work. History is on each side you turn, and down town Chicago is minutes away. It is a public transportation dream, so you can park the car if you wish. Come share in the experience that Vintage Ambience provides.

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4.9 out of 5 average rating, 98 reviews

The open living area features a modern staircase with wooden steps and a metal railing. A light-colored sofa adorned with decorative cushions faces a dining space with a large table and stylish light fixtures. Exposed brick walls add warmth to the contemporary decor.

Townhouse in South Side

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.

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4.79 out of 5 average rating, 148 reviews

A well-appointed bedroom features a cozy bed with a dark patterned blanket, complemented by decorative pillows. Natural light enters through a window, creating a bright ambiance. A stylish bedside lamp and a small nightstand add functionality to the space, alongside a decorative wall art piece.

Apartment in Hyde Park

Best Location in Hyde Park apartment

Lovely 2 bedroom apartment in Hyde Park. Within one block of the U of Chicago. The lake is within a 10min walk. Ample Street Parking available in safe street patroled by UChicGo police. 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. Extra cleaning fee for 2nd bedroom. Great view to the park and tennis courts and porch on the kitchen to enjoy breakfast outside.

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An inviting living area features hardwood flooring and large windows allowing natural light. A plush sofa with dark cushions is complemented by a unique accent chair. A contemporary chandelier hangs from the ceiling, and a mirror is mounted on the wall, reflecting the cozy ambiance.

4.94 out of 5 average rating, 67 reviews

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.

ValueFamilyLong stay

4.98 out of 5 average rating, 47 reviews

Apartment in South Side

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.

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Top guest favorite

A spacious sleeping area is showcased with a neatly made bed featuring a blue comforter. Two brown chairs are positioned beside a round area rug, and sunlight enters through two large windows. Framed artwork is displayed on the gray wall.

5 out of 5 average rating, 24 reviews

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!

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4.94 out of 5 average rating, 17 reviews

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!

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The exterior of a two-story condo building is presented, featuring dark brick and a light-colored stone facade. A decorative wreath is hung on the front door, and colorful pumpkins are arranged on steps alongside a ghost figure. Beside the entrance, a small yellow table and chairs contribute to the outdoor ambiance.