House accommodation & holiday rentals in West Side
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Top-rated house accommodation & rentals in West Side
Guests agree: These houses are highly rated for location, cleanliness and more.
Holiday 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
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Home in Chicago
4.87 out of 5 average rating, 38 reviewsLuxury Cabin in Lakeview
Home in Schaumburg
5.0 out of 5 average rating, 3 reviewsParadise 4BR w/ Pool & Games
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
4.98 out of 5 average rating, 175 reviewsThe Evergreen House
Home in Chicago
4.89 out of 5 average rating, 36 reviewsBrand New Spacious Duplex
Home in Berwyn
4.99 out of 5 average rating, 84 reviewsRetro Modern Bungalow | free parking | fire pit
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 Chicago
4.86 out of 5 average rating, 69 reviewsChicago getaway for two!
Home in Chicago
4.91 out of 5 average rating, 90 reviewsBoho Chic Coach House 30Min to downtown W/ Parking
Home in Oak Park
4.95 out of 5 average rating, 42 reviewsCozy & comfy w/free parking & W/D
Private house rentals
Home in Chicago
5.0 out of 5 average rating, 51 reviewsCozy, Quiet, Riverwalk Sanctuary
Home in Chicago
4.93 out of 5 average rating, 73 reviewsModern Lux Getaway w/ Hot Tub, Lrg Yard, Parking
Home in Chicago
5.0 out of 5 average rating, 52 reviewsCharming 3-BED in Lincoln Park/ Old Town & Parking
Home in Chicago
4.96 out of 5 average rating, 25 reviewsCharming and Classic Brick Home in Bridgeport
Home in Oak Park
4.97 out of 5 average rating, 61 reviewsModern Victorian Charm | A+ Location in OP
Home in Chicago
4.94 out of 5 average rating, 16 reviewsSteel and Sky
Home in Chicago
4.94 out of 5 average rating, 49 reviewsCozy space in Wicker Park
Home in Chicago
4.97 out of 5 average rating, 32 reviewsLight and bright 3BD duplex in Avondale, Chicago
Destinations to explore
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