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*
Mar 31 – Apr 7
Home in Schaumburg
5.0 out of 5 average rating, 3 reviewsParadise 4BR w/ Pool & Games
Nov 21 – 28
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Jan 16 – 23
Home in Plainfield
4.95 out of 5 average rating, 62 reviewsUnique Spanish style Home (w/heated pool)
Aug 14 – 21
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, 17 reviewsGlen Ellyn Home
Jul 23 – 30
Home in Chicago
4.8 out of 5 average rating, 15 reviews2Bed+2Bath PentHouse in South Loop
Feb 11 – 18
Home in Carol Stream
4.55 out of 5 average rating, 20 reviewsAmazing Summer Pool Awaits You!
Nov 6 – 13
Weekly house rentals
Home in Des Plaines
4.78 out of 5 average rating, 308 reviewsUrban Farmhouse near O'Hare
Apr 21 – 28
Home in Chicago
4.88 out of 5 average rating, 64 reviewsChicago getaway for two!
Mar 11 – 18
Home in Chicago
4.98 out of 5 average rating, 50 reviewsCity Cottage in Logan Square-Avondale
Oct 2 – 9
Home in Chicago
4.89 out of 5 average rating, 36 reviewsBrand New Spacious Duplex
Aug 19 – 26
Home in Wilmette
4.98 out of 5 average rating, 92 reviewsUnique porcelain-enamel paneled "Lustron" home
Oct 2 – 9
Home in Chicago
4.86 out of 5 average rating, 29 reviews3BD/2BA Chicago Avondale/Logan Square House
Dec 9 – 16
Home in Berwyn
5.0 out of 5 average rating, 78 reviewsRetro Modern Bungalow | free parking | fire pit
Dec 2 – 9
Home in Chicago
4.98 out of 5 average rating, 87 reviews3BD Home Mins from Airport | Free Wi-Fi + Parking
Sep 11 – 18
Private house rentals
Home in Chicago
5.0 out of 5 average rating, 33 reviewsBright & Spacious 4BR Home in Heart of Logan Sq!
Nov 27 – Dec 4
Home in Chicago
5.0 out of 5 average rating, 24 reviewsLovely 6 Bd Retreat w/ Game Room, Back Deck & Bar
Nov 6 – 13
Home in Chicago
4.97 out of 5 average rating, 70 reviewsCasita Rosalinda - 3BR/2BA Chicago Home
Sep 4 – 11
Home in Chicago
5.0 out of 5 average rating, 5 reviews1-bedroom with full kitchen, washer/dryer inside
Nov 3 – 10
Home in Chicago
4.97 out of 5 average rating, 34 reviewsSingle Family Home in Logan w/ 2 Car Garage
Jul 20 – 27
Home in Chicago
4.98 out of 5 average rating, 55 reviews2BD/1 BA with summer patio in quiet Roscoe Village
Nov 29 – Dec 6
Home in Chicago
4.94 out of 5 average rating, 31 reviewsFurnished 3 Bedroom 2 Bathroom home.
Jul 15 – 22
Home in Oak Park
4.95 out of 5 average rating, 37 reviewsCozy & comfy w/free parking & W/D
Jul 28 – Aug 4
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