House vacation rentals in Woodlawn, Chicago
Find and book unique houses on Airbnb
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 Chicago
4.86 out of 5 average rating, 36 reviewsLuxury Cabin in Lakeview
Jul 7 – 12
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Apr 18 – 25
Home in Glen Ellyn
4.94 out of 5 average rating, 16 reviewsGlen Ellyn Home
May 6 – 13
Home in Chicago Heights
Olympia field -matteson IL- homewood, park forest
Aug 24 – 31
Home in Chicago
4.8 out of 5 average rating, 15 reviews2Bed+2Bath PentHouse in South Loop
Nov 23 – 30
Home in Schererville
5.0 out of 5 average rating, 3 reviewsCozy house in Schererville
Nov 25 – Dec 2
Home in Olympia Fields
4.58 out of 5 average rating, 31 reviewsLuxurious South Suburban Villa
Oct 6 – 13
Home in New Lenox
4.74 out of 5 average rating, 34 reviewsCheerful home. Heated pool, Hot tub!
Aug 26 – Sep 2
Weekly house rentals
Home in Chicago
4.8 out of 5 average rating, 15 reviewsCozy 2 bed Condo in Bronzeville!
Nov 29 – Dec 6
Home in Chicago
5.0 out of 5 average rating, 15 reviewsCozy Haven
Jun 4 – 11
Home in Chicago
4.91 out of 5 average rating, 87 reviewsBoho Chic Coach House 30Min to downtown W/ Parking
Jan 9 – 16
Home in Chicago
4.9 out of 5 average rating, 29 reviewsCheerful 3 Bedroom, City Oasis
Oct 3 – 10
Home in Chicago
4.82 out of 5 average rating, 96 reviewsWoodlawn Oasis: 5-15 Mins from Food, Fun, Dining
Nov 13 – 20
Home in Chicago
4.95 out of 5 average rating, 19 reviewsSpacius unit in historic gem
Aug 21 – 28
Home in Chicago
4.86 out of 5 average rating, 14 reviewsGarden Apartment in Gated Home
Mar 9 – 16
Home in Chicago
4.88 out of 5 average rating, 42 reviewsCozy Chicago House near Hyde Park!
Apr 4 – 11
Private house rentals
Home in Munster
4.97 out of 5 average rating, 34 reviewsEntire home: Private, Cozy Oasis in Quiet Locale
Apr 6 – 13
Home in Chicago
5.0 out of 5 average rating, 15 reviewsChicago Home by Midway near Downtown Attractions
Jan 27 – Feb 3
Home in Munster
5.0 out of 5 average rating, 12 reviewsCozy Farmhouse in Munster
Jun 13 – 20
Home in Chicago
4.92 out of 5 average rating, 12 reviewsBeverly Cottage House
Jul 6 – 13
Home in Calumet Park
4.95 out of 5 average rating, 22 reviewsMy quaint little escape
Dec 3 – 10
Home in Chicago
5.0 out of 5 average rating, 18 reviewsHyde Park Haven: Exquisite Airbnb
Oct 7 – 14
Home in Chicago
4.92 out of 5 average rating, 12 reviewsExperience Chicago from Our 3-Story Retreat
Jan 7 – 14
Home in Chicago
4.96 out of 5 average rating, 27 reviewsLakeview Condo
Feb 7 – 14
Quick stats about house rentals in Woodlawn, Chicago
Total rentals
40 properties
Wifi availability
40 properties include access to wifi
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
1.5K reviews
Nightly prices starting at
€ 19 before taxes and fees
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