House vacation rentals in West Side
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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 Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Aug 24 – 31
Home in Chicago
4.86 out of 5 average rating, 37 reviewsLuxury Cabin in Lakeview
Jul 7 – 14
Home in Glen Ellyn
4.94 out of 5 average rating, 16 reviewsGlen Ellyn Home
Jul 23 – 30
Home in Schaumburg
5.0 out of 5 average rating, 3 reviewsParadise 4BR w/ Pool & Games
Nov 12 – 19
Home in Gary
4.82 out of 5 average rating, 213 reviewsOasis , Near Beach, Hard Rock and Dunes
Apr 3 – 10
Home in Chicago
4.8 out of 5 average rating, 15 reviews2Bed+2Bath PentHouse in South Loop
Feb 2 – 9
Home in Plainfield
4.89 out of 5 average rating, 27 reviewsPool* King beds* Grill & Patio* 30mi to Chicago
Aug 7 – 14
Home in Bartlett
5.0 out of 5 average rating, 4 reviewsFully Furnished Executive Home, Lux Amenities
Dec 11 – 18
Weekly house rentals
Home in Chicago
4.98 out of 5 average rating, 50 reviewsCity Cottage in Logan Square-Avondale
Oct 3 – 10
Home in Oak Park
4.95 out of 5 average rating, 37 reviewsCozy & comfy w/free parking & W/D
Jul 14 – 19
Home in Chicago
4.91 out of 5 average rating, 88 reviewsBoho Chic Coach House 30Min to downtown W/ Parking
Dec 28 – Jan 4
Home in Chicago
4.87 out of 5 average rating, 63 reviewsChicago getaway for two!
Jan 19 – 26
Home in Chicago
5.0 out of 5 average rating, 48 reviewsCozy, Quiet, Riverwalk Sanctuary
Nov 9 – 16
Home in Chicago
5.0 out of 5 average rating, 15 reviewsChicago Home by Midway near Downtown Attractions
Oct 19 – 26
Home in Chicago
4.98 out of 5 average rating, 54 reviews2BD/1 BA with summer patio in quiet Roscoe Village
Apr 3 – 10
Home in Wilmette
4.98 out of 5 average rating, 92 reviewsUnique porcelain-enamel paneled "Lustron" home
Sep 11 – 18
Private house rentals
Home in Chicago
5.0 out of 5 average rating, 7 reviewsThe Full House
Nov 4 – 11
Home in Chicago
5.0 out of 5 average rating, 46 reviewsCharming 3-BED in Lincoln Park/ Old Town & Parking
Nov 9 – 16
Home in Chicago
5.0 out of 5 average rating, 20 reviews4BD/4BTH - Entire Building+Garage - Wicker Park!
Dec 17 – 24
Home in Berwyn
4.95 out of 5 average rating, 22 reviewsBerwyn Beauty
Feb 16 – 23
Home in Chicago
4.96 out of 5 average rating, 27 reviewsLakeview Condo
Nov 18 – 25
Home in Cicero
4.95 out of 5 average rating, 22 reviewsSpacious 3br house near Downtown Chicago & Airport
Jan 8 – 15
Home in Chicago
4.98 out of 5 average rating, 87 reviews3BD Home Mins from Airport | Free Wi-Fi + Parking
Sep 11 – 18
Home in Chicago
4.96 out of 5 average rating, 23 reviewsCharming and Classic Brick Home in Bridgeport
Oct 16 – 23
Destinations to explore
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- Monthly Rentals West Side
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