House vacation rentals in Northwest Side
Find and book unique houses on Airbnb
Top-rated house rentals in Northwest 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 Northwest Side house rentals
House rentals with a pool
Home in Highland Park
4.9 out of 5 average rating, 125 reviews2-Acre Highland Park Retreat with Heated Pool ~ 5*
Nov 14 – 21
Home in Schaumburg
5.0 out of 5 average rating, 3 reviewsParadise 4BR w/ Pool & Games
Nov 21 – 28
Home in Plainfield
4.95 out of 5 average rating, 62 reviewsSpanish style Home (w/heated pool)
Sep 17 – 24
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Nov 19 – 26
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 Lake Forest
4.91 out of 5 average rating, 58 reviewsBeautiful 137 Year Old Farm Home (3night min)
Apr 8 – 15
Home in Chicago Heights
Olympia field -matteson IL- homewood, park forest
Jul 22 – 29
Weekly house rentals
Home in Des Plaines
4.78 out of 5 average rating, 307 reviewsUrban Farmhouse near O'Hare
Aug 11 – 18
Home in Chicago
4.98 out of 5 average rating, 50 reviewsCity Cottage in Logan Square-Avondale
Oct 3 – 10
Home in Chicago
4.87 out of 5 average rating, 63 reviewsChicago getaway for two!
Apr 10 – 17
Home in Chicago
4.9 out of 5 average rating, 20 reviewsNorthside Chicago Getaway
Mar 10 – 17
Home in Chicago
4.89 out of 5 average rating, 35 reviewsBrand New Spacious Duplex
Oct 22 – 29
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 Wilmette
4.98 out of 5 average rating, 92 reviewsUnique porcelain-enamel paneled "Lustron" home
Sep 23 – 30
Home in Berwyn
5.0 out of 5 average rating, 78 reviewsRetro Modern Bungalow | free parking | fire pit
Nov 18 – 25
Private house rentals
Home in Chicago
4.97 out of 5 average rating, 77 reviewsUltra Modern, 2800 SQ Ft, Outdoor Gazebo Sleeps 14
Mar 23 – 30
Home in Chicago
5.0 out of 5 average rating, 19 reviewsHome in Chicago
Jun 25 – Jul 2
Home in Chicago
5.0 out of 5 average rating, 32 reviewsBright & Spacious 4BR Home in Heart of Logan Sq!
Apr 8 – 15
Home in Chicago
4.97 out of 5 average rating, 33 reviewsSingle Family Home in Logan w/ 2 Car Garage
Sep 30 – Oct 7
Home in Chicago
4.94 out of 5 average rating, 31 reviewsFurnished 3 Bedroom 2 Bathroom home.
Nov 28 – Dec 5
Home in Chicago
4.96 out of 5 average rating, 27 reviewsLakeview Condo
Feb 20 – 27
Home in Oak Park
4.97 out of 5 average rating, 59 reviewsModern Victorian Charm | A+ Location in OP
Jul 6 – 13
Home in Chicago
4.97 out of 5 average rating, 70 reviewsCasita Rosalinda - 3BR/2BA Chicago Home
Sep 4 – 11
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