House vacation rentals in West Side
Find and book unique houses on Airbnb
Top-rated house rentals in West Side
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 West Side house rentals
House rentals with a pool
Home in Highland Park
4.9 out of 5 average rating, 126 reviews2-Acre Highland Park Retreat with Heated Pool ~ 5*
Home in Gary
4.93 out of 5 average rating, 126 reviewsBayless Dune Lodge at West Beach - Indiana Dunes!
Home in Plainfield
4.95 out of 5 average rating, 63 reviewsLarge Spanish style Home (w/heated pool)
Home in Schaumburg
5.0 out of 5 average rating, 3 reviewsParadise 4BR w/ Pool & Games
Home in Chicago
4.87 out of 5 average rating, 38 reviewsLuxury Cabin in Lakeview
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Home in Glen Ellyn
4.94 out of 5 average rating, 17 reviewsGlen Ellyn Home
Home in Lake Forest
4.91 out of 5 average rating, 58 reviewsBeautiful 137 Year Old Farm Home (3night min)
Weekly house rentals
Home in Chicago
4.84 out of 5 average rating, 83 reviewsFree parking, close to public transit, dining
Home in Maywood
4.83 out of 5 average rating, 63 reviewsMaywood Relaxation
Home in Oak Park
4.95 out of 5 average rating, 42 reviewsCozy & comfy w/free parking & W/D
Home in Chicago
4.91 out of 5 average rating, 90 reviewsBoho Chic Coach House 30Min to downtown W/ Parking
Home in Chicago
4.85 out of 5 average rating, 68 reviewsChicago getaway for two!
Home in Chicago
4.94 out of 5 average rating, 49 reviewsCozy space in Wicker Park
Home in Chicago
4.98 out of 5 average rating, 51 reviewsCity Cottage in Logan Square-Avondale
Home in Chicago
5.0 out of 5 average rating, 50 reviewsCozy, Quiet, Riverwalk Sanctuary
Private house rentals
Home in Chicago
5.0 out of 5 average rating, 18 reviewsChicago Home by Midway near Downtown Attractions
Home in Forest Park
4.94 out of 5 average rating, 70 reviewsAdorable house Madison Street w/ 2 car garage!
Home in Oak Park
4.96 out of 5 average rating, 77 reviewsClean, Cozy Duplex with Kitchen & Free Parking
Home in Chicago
4.98 out of 5 average rating, 57 reviews2BD/1 BA with summer patio in quiet Roscoe Village
Home in Chicago
5.0 out of 5 average rating, 12 reviewsModern Family-Friendly Home in the Heart of Pilsen
Home in Chicago
5.0 out of 5 average rating, 52 reviewsCharming 3-BED in Lincoln Park/ Old Town & Parking
Home in Chicago
4.94 out of 5 average rating, 16 reviewsSteel and Sky
Home in Chicago
4.97 out of 5 average rating, 32 reviewsLight and bright 3BD duplex in Avondale, Chicago
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