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 Highland Park
4.9 out of 5 average rating, 125 reviews2-Acre Highland Park Retreat with Heated Pool ~ 5*
Apr. 16 – 23
Home in Chicago
4.86 out of 5 average rating, 36 reviewsLuxury Cabin in Lakeview
Jul. 7 – 12
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
May 25 – Jun. 1
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)
Jan. 12 – 19
Home in Schaumburg
New place to stayParadise 4BR w/ Pool & Games
Aug. 5 – 12
Home in Chicago
4.8 out of 5 average rating, 15 reviews2Bed+2Bath PentHouse in South Loop
Nov. 23 – 30
Home in Carol Stream
4.55 out of 5 average rating, 20 reviewsAmazing Summer Pool Awaits You!
Nov. 3 – 10
Weekly house rentals
Home in Chicago
4.98 out of 5 average rating, 175 reviewsThe Evergreen House
Jun. 20 – 27
Home in Chicago
4.92 out of 5 average rating, 111 reviewsSpacious Two Story Luxurious Home w/Outdoor Deck!
Mar. 8 – 15
Home in Chicago
4.83 out of 5 average rating, 136 reviewsLincoln Park - DePaul House w/Patio Free Parking
Sep. 3 – 10
Home in Chicago
4.95 out of 5 average rating, 262 reviewsThe Roscoe House near Wrigley Field
Dec. 6 – 13
Home in Chicago
4.87 out of 5 average rating, 62 reviewsChicago getaway for two!
Mar. 19 – 26
Home in Chicago
5.0 out of 5 average rating, 12 reviewsHidden Gem on the CHI north side
Sep. 14 – 21
Home in Chicago
4.88 out of 5 average rating, 26 reviewsPrivate Condo in Chicago w/ Parking, Near Evanston
Oct. 15 – 22
Home in Chicago
4.96 out of 5 average rating, 27 reviewsLakeview Condo
Feb. 7 – 14
Private house rentals
Home in Chicago
4.99 out of 5 average rating, 70 reviewsWhole apartment! 2 Bed/2 bath steps from Wrigley!!
Feb. 16 – 23
Home in Chicago
4.98 out of 5 average rating, 87 reviews3BD Home Mins from Airport | Free Wi-Fi + Parking
Sep. 21 – 28
Home in Chicago
5.0 out of 5 average rating, 11 reviewsCubby Blue home - Wrigley ~Free Parking~
Jan. 12 – 19
Home in Chicago
4.97 out of 5 average rating, 70 reviewsEntire first floor in Lincoln Square!
Dec. 10 – 17
Home in Wilmette
4.98 out of 5 average rating, 92 reviewsUnique porcelain-enamel paneled "Lustron" home
Sep. 23 – 30
Home in Chicago
4.89 out of 5 average rating, 35 reviewsBrand New Spacious Duplex
Oct. 8 – 15
Home in Chicago
4.98 out of 5 average rating, 60 reviewsVictorian House in Heart of Rogers Park
Sep. 8 – 15
Home in Chicago
4.86 out of 5 average rating, 14 reviewsLuxury 1BR Suite | Lincoln Square
Jul. 24 – 31
Destinations to explore
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