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
Home in Munster
5 out of 5 average rating, 8 reviewsMunster hide away
Home in Lockport
New place to stayHidden GEM OASIS in Chicagoland
Home in Glenwood
4.79 out of 5 average rating, 53 reviewsSpacious Family Glenwood Estates Home w/ Hot Tub!
Home in Forest Glen
New place to stayCity Close, Country Calm
Home in Near South Side
4.86 out of 5 average rating, 29 reviews2Bed+2Bath PentHouse in South Loop
Weekly house rentals
Home in Chicago
5 out of 5 average rating, 3 reviewsThe Modern Muse of Chicago! Close to everything!
Home in Hyde Park
5 out of 5 average rating, 11 reviewsAmazing historic campus mansion!
Home in Woodlawn
4.91 out of 5 average rating, 44 reviewsCheerful 3 Bedroom, City Oasis
Home in Bridgeport
4.86 out of 5 average rating, 100 reviewsFree parking, close to public transit, dining
Home in Chicago
4.81 out of 5 average rating, 36 reviewsExec Lux home wth 3 Level,6 Bdrms/3bth & 2 Kitchen
Home in South Shore
5 out of 5 average rating, 8 reviewsSpacious 4BR Oasis Near Lake Michigan
Home in Hyde Park
4.87 out of 5 average rating, 30 reviewsA Family Rowhouse by UChicago
Home in Chicago
4.93 out of 5 average rating, 43 reviewsSpacius unit in historic gem
Private house rentals
Home in Gold Coast
5 out of 5 average rating, 6 reviewsGold Coast Pristine 4BR/4.5BA Home | Free Parking.
Home in Roseland
4.93 out of 5 average rating, 44 reviewsExperience Chicago from Our 3-Story Retreat
Home in Hyde Park
4.91 out of 5 average rating, 11 reviewsWalk to U of Chicago! Modern home, parking, yard
Home in Bridgeport
4.97 out of 5 average rating, 39 reviewsCharming and Classic Brick Home in Bridgeport
Home in Kenwood
5 out of 5 average rating, 16 reviewsVilla Noir Chicago Victorian 7 min to downtown
Home in Chicago
5 out of 5 average rating, 5 reviewsSmart Home King Bed Private Yard
Home in Beverly
4.92 out of 5 average rating, 64 reviewsBeverly House
Home in Bridgeport
4.98 out of 5 average rating, 85 reviewsCozy, Quiet, Riverwalk Sanctuary
Quick stats about house rentals in Woodlawn, Chicago
Total rentals
40 properties
Nightly prices starting at
$30 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
30 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi
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