Vacation rentals in Woodlawn

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Top-rated vacation rentals in Woodlawn

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Guest favorite

Vacation home in Jackson Park Highlands

4.94 out of 5 average rating, 80 reviews

UChicago Luxurious King Suite Lakefront

Sink into a pillowtop king size bed in a sunny, spacious bedroom suite w/twin bed, his/hers closets and comfy love seat. Spacious 1,000 s.f. condo luxury, kitchens /bath with granite counters, office space, 3rd-floor unit, private entrance gated and on-street parking. 1 min walk to beach, trails, golf course and bike rental. Located 1 blk from Express bus (15 minutes) to Univ of Chicago/Hyde Park and Museum of Science and Industry,(20 minutes) to Soldier Field, Grant Park, Downtown, Navy Pier

Superhost

Condo in South Side

4.91 out of 5 average rating, 58 reviews

Modern Apt Near U of Chicago!

Stay here in our warm apartment, a stone's throw away from the University of Chicago school and hospital! Ideal for families, scholars, students, vacationers or business travelers. Sleeps 6 (2 twin memory foam floor mattresses available). Free street parking! Close to Museum of Science and Industry, Robie House, golf courses, lake, grocery and charming streets of Hyde Park. Great shops and restaurants! Public transportation close by to travel into the city and explore Downtown Chicago as well.

Guest favorite

Condo in Woodlawn

4.96 out of 5 average rating, 46 reviews

University of Chicago Condo-Upgraded and Spacious

Beautiful, spacious, 1 bedrm, 2 bathrm condo near the University of Chicago. Open floorplan, hardwd floors, stainless appliances, 2 Smart TVs in bedrm & living rm, in-unit laundry, and private parking space. Features a cozy reading nook and large outdoor patio. On a quiet treelined street - minutes from Hyde Park and waking distance to Lake Michigan, Jackson Park Golf Course, the 222,000sq ft Regal Mile Film Studios, and upcoming Obama Presidential Library. Your stylish home away from home!

Superhost

Apartment in South Side

4.77 out of 5 average rating, 48 reviews

Spacious Haven Near Green Line, 20mins to Downtown

Nestled in the charming, tree-lined streets of West Woodlawn, this cozy spot invites you to explore the best of Chicago! Just steps away from the serene Washington Park, complete with playgrounds, serene hiking trails, and a lovely pond that’s perfect for a morning walk or some quiet reflection. Craving a taste of Hyde Park’s vibrant culinary scene? You’re just minutes from its top restaurants. With the Green Line train just a quick 7-minute walk away, you can be downtown in no time!

Guest favorite

Townhouse in Woodlawn

4.92 out of 5 average rating, 62 reviews

*Hyde Park *2 Masters *2 Living Rooms *Courtyard

Welcome to our newly renovated retreat, The Urban Oasis in 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 small groups as you explore everything Chicago has to offer.

Superhost

Apartment in South Shore

4.77 out of 5 average rating, 39 reviews

South Shore Oasis

Discover South Shore's charm in this renovated 1-bed basement apt within the owner's home, perfect for UChicago visitors—parents, graduates, and professionals. Though outside Hyde Park, it's just a 5-min walk to transit, offering quick access to campus and downtown. Enjoy the lakefront, bike trail, and beach nearby. Separate entrance ensures privacy, with the owner on-site for local tips. Experience tranquility with easy access to excitement. Book now for memorable stays!

Guest favorite

Apartment in Washington Park

4.98 out of 5 average rating, 43 reviews

Private Duplex w/ Theater + Games | Near UChicago

Enjoy our spacious 2-level home this fall and winter, perfect for families and groups. The lower level is your entertainment hub with a 120" projector, retro arcade, ping pong, board games, reclining sectional, 1 bedroom, and 1 bath. Upstairs features two bedrooms, a full bath, an electric fireplace for cozy nights, a fully stocked kitchen with coffee, and a furnished patio. Kids and young adults especially love the fun setup, making it a memorable Chicago stay for all.

Guest favorite

Apartment in South Side

4.93 out of 5 average rating, 127 reviews

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).

Guest favorite

Apartment in South Side

5 out of 5 average rating, 15 reviews

NEW Eco Stay by UChicago, Lakefront & Hyde Park!

Enjoy comfort and sustainability in this beautifully designed South Side retreat. Located in a modern, solar-powered green home, this space is perfect for guests looking for both relaxation and access to Chicago’s top attractions. Just minutes from Hyde Park, Jackson Park, the Obama Presidential Center, the University of Chicago, Museum of Science and Industry and Lake Michigan where you’re well-placed to explore both culture and nature.

Apartment in Washington Park

4.79 out of 5 average rating, 52 reviews

W3N NexttoUniversityTrainPark 15minsDowntown Desk

☞ 1 Smart TV ☞ Fully equipped + stocked kitchen ☞ Self check-in ✭“Everything I needed to have a great vacation thank you ” ☞ Luggage storage available ☞ Onsite washer + dryer in basement ☞ Air conditioning 》30 mins to airports 》15 mins to Downtown Chicago 》 Walking distance to University of Chicago, L train, Park 》15 mins to McCormick Place convention, Millennium Park, museum campus 》Sleeps 6 》2 bedroom 》1 bathroom

Guest favorite

Condo in Woodlawn

5 out of 5 average rating, 10 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!

Condo in Woodlawn

4.87 out of 5 average rating, 252 reviews

A Stones Throw from U Chicago South Campus!

This 2 bedroom garden unit located in vintage World's Columbian Exposition era building, it's been renovated and updated. You can't get much closer to the University of Chicago campus. This quiet garden unit is within walking distance of lakefront beaches, golf courses, the Museum of Science and Industry, public transportation, and Jackson Park. No pets allowed.