House vacation rentals in North Side
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Top-rated house rentals in North 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 North Side house rentals
House rentals with a pool
Home in Chicago
4.86 out of 5 average rating, 37 reviewsLuxury Cabin in Lakeview
Jul 7 – 14
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Aug 24 – 31
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 Chicago
4.8 out of 5 average rating, 15 reviews2Bed+2Bath PentHouse in South Loop
Feb 2 – 9
Home in Bartlett
5.0 out of 5 average rating, 4 reviewsFully Furnished Executive Home, Lux Amenities
Dec 11 – 18
Home in Carol Stream
4.55 out of 5 average rating, 20 reviewsAmazing Summer Pool Awaits You!
Jul 29 – Aug 5
Home in Plainfield
4.89 out of 5 average rating, 27 reviewsPool* King beds* Grill & Patio* 30mi to Chicago
Aug 7 – 14
Weekly house rentals
Home in Chicago
4.92 out of 5 average rating, 111 reviewsSpacious Two Story Luxurious Home w/Outdoor Deck!
Jan 19 – 26
Home in Chicago
4.93 out of 5 average rating, 134 reviewsSuperhost Wrigley/Lakeview Duplex 3BR/2.5BA
Aug 16 – 23
Home in Chicago
4.83 out of 5 average rating, 136 reviewsLincoln Park - DePaul House w/Patio Free Parking
Sep 8 – 15
Home in Chicago
4.98 out of 5 average rating, 175 reviewsThe Evergreen House
Jun 29 – Jul 6
Home in Chicago
5.0 out of 5 average rating, 5 reviews1-bedroom with full kitchen, washer/dryer inside
Dec 4 – 11
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, 12 reviewsHidden Gem on the CHI north side
Aug 16 – 23
Home in Chicago
4.91 out of 5 average rating, 88 reviewsBoho Chic Coach House 30Min to downtown W/ Parking
Nov 30 – Dec 7
Private house rentals
Home in Wilmette
4.98 out of 5 average rating, 92 reviewsUnique porcelain-enamel paneled "Lustron" home
Sep 11 – 18
Home in Chicago
4.96 out of 5 average rating, 27 reviewsLakeview Condo
Dec 6 – 13
Home in Chicago
4.99 out of 5 average rating, 71 reviewsWhole apartment! 2 Bed/2 bath steps from Wrigley!!
Jan 25 – Feb 1
Home in Berwyn
5.0 out of 5 average rating, 78 reviewsRetro Modern Bungalow | free parking | fire pit
Nov 15 – 22
Home in Chicago
5.0 out of 5 average rating, 15 reviewsChicago Home by Midway near Downtown Attractions
Oct 19 – 26
Home in Chicago
4.88 out of 5 average rating, 26 reviewsPrivate Condo in Chicago w/ Parking, Near Evanston
Sep 16 – 23
Home in Chicago
4.98 out of 5 average rating, 61 reviewsVictorian House in Heart of Rogers Park
Sep 17 – 24
Home in Skokie
4.96 out of 5 average rating, 28 reviewsLuxe Limewash Getaway w/Sun Deck
Jan 18 – 25
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