The Study at the University of Chicago 
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9.1 (1047 Reviews) Hotel
Private parking • Restaurant • Pet friendly
Best Price Match Woodlawn Luxury Rental Homes and Villas
Find Luxury Places to Stay Near Woodlawn. Find luxury in Woodlawn, Chicago.
Sophy Hyde Park Best Price Match
9.0 (202 Reviews) Hotel
Private parking • Restaurant • Pet friendly
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The Penthouse, Lux stay near Downtown, UofC & Lake Best Price Match
9.2 (37 Reviews) Apartment
The entire place is yours • 135 m² size • Kitchen
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Chic Euro City Getaway- Close to Downtown Best Price Match
8.4 (29 Reviews) Apartment
The entire place is yours • 111 m² size • Free WiFi
Chicago Grand Boulevard • In Woodlawn · 3.5km to center
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BOUTIQUE GARDEN HOUSE CHICAGO 3-STORY sleeps 12 Best Price Match
9.7 (6 Reviews) Holiday_home
The entire place is yours • 139 m² size • Free on-site parking
Chicago Greater Grand Crossing • In Woodlawn · 2.7km to center
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Forrestville Ave Large Suite Best Price Match
8.6 (103 Reviews) Apartment
The entire place is yours • 130 m² size • Free parking
Chicago Grand Boulevard • In Woodlawn · 4.1km to center
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Beautifully Renovated House 10 mins from Downtown Best Price Match
8.3 (12 Reviews) Holiday_home
The entire place is yours • 297 m² size • Kitchen
Chicago Grand Boulevard • In Woodlawn · 4.8km to center
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Beautiful Big 3 bedroom Quiet Apt near downtown Best Price Match
8.5 (23 Reviews) Apartment
The entire place is yours • 149 m² size • Free on-site parking
Chicago South Shore • In Woodlawn · 3.1km to center
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New Luxurious 5BD-2BA Duplex-FREE WINE-2CAR Parking Best Price Match
9.1 (18 Reviews) Apartment
The entire place is yours • 158 m² size • Free on-site parking
Chicago Avalon Park • In Woodlawn · 4.5km to center
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The Brown House - A luxurious UChicago Campus stay Best Price Match
10.0 (5 Reviews) Apartment
The entire place is yours • 139 m² size • Free on-site parking
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Eco Stay by UChicago, Lakefront & Hyde Park! Best Price Match
9.0 (5 Reviews) Apartment
The entire place is yours • 74 m² size • Free on-site parking
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Chateau de Woodlawn - Peaceful 3 bedroom apartment. Best Price Match
8.9 (15 Reviews) Apartment
The entire place is yours • 108 m² size • Kitchen
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Sleek 1-Bedroom Apt in Chicago - East Park Tower 0610 rep Best Price Match
8.8 (6 Reviews) Apartment
The entire place is yours • 58 m² size • Pet friendly
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Cozy & Radiant 2BR Apartment - BStone 605 Best Price Match
8.5 (6 Reviews) Apartment
The entire place is yours • 124 m² size • Pet friendly
Best Price Match About Woodlawn Luxury Rental on NearbyHoliday
Looking for luxury in Woodlawn? Compare top options in Chicago.
Searching for a luxury place to stay in or near Woodlawn? We have more than 14 luxury homes, private retreats, luxury villas, 5-star hotels, cottages, and condos that you can stay at in Woodlawn.
NearbyHoliday has a variety of luxury rentals, including vacation homes, apartments, chalets, luxury penthouses, lake homes, beachfront resorts, private villas, and many luxury lifestyle options, many in Woodlawn. Whether you are traveling with families or groups, hosting a get-together, or a cocktail party, we have the perfect place to stay for your travel plans. Our places to stay in Woodlawn are located in the top buildings and neighborhoods and many come with luxury features throughout the living areas, kitchens, and bedrooms, including private pools, hot tubs, home theatres, amazing views, and plenty of space to relax. Get more room with NearbyHoliday.