
House vacation rentals in Woodlawn, Chicago
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Top-rated house rentals in Woodlawn, Chicago
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Woodlawn, Chicago house rentals
House rentals with a pool

Luxurious South Suburban Villa

Munster hide away

Hidden GEM OASIS in Chicagoland

Rosemont 4BD2BA house with Pool

Luxe heated indoor pool/hot tub

Celebrate at Hacjenda house

Luxury Loft with Private Pool and Movie Theater

Luxury fenced in modern ranch
Weekly house rentals

Family Friendly Duplex/9 min from MDW/Free Parking

Lux_Home Chicago 8 mins Downtown

Warm bungalow in New City

CasaNova Modern City Living

Experience Chicago from Our 3-Story Retreat

Cozy getaway in the city.

Charming 3 bed home with private backyard

Villa Noir Chicago Victorian 7 min to downtown
Private house rentals

Modern Charming Home w/Pergola & games

Garden/unit/1+1/cosy

Cozy, King/Queen bed, 2 bedroom.

Cozy Modern Home w/Fireplace & Pond

Gorgeous 2Bedroom House…

Luxury-Near Downtown & United Center-Sleeps 14

Spacious 3 Level Home with 5 BDR/3 BA & 2 Kitchens

Laurna Dune
Quick stats about house rentals in Woodlawn, Chicago
Total rentals
60 properties
Nightly prices starting at
G$6,276 GYD before taxes and fees
Total number of reviews
1.7K reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Wifi availability
60 properties include access to wifi
Destinations to explore
- Condo rentals Woodlawn
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- Kid-friendly rentals Woodlawn
- Rentals with a patio Woodlawn
- Rentals with lake access Woodlawn
- Pet-friendly rentals Woodlawn
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Six Flags Great America
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Wicker Park
- Illinois Beach State Park
- Brookfield Zoo
- Washington Park Zoo
- The 606
- The Beverly Country Club
- Moraine Hills State Park