House vacation rentals in North Side
Find and book unique houses on Airbnb
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
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
Nov 4 – 11
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
Dec 15 – 22
Home in Bartlett
5.0 out of 5 average rating, 5 reviewsFully Furnished Executive Home, Lux Amenities
Feb 19 – 26
Home in Carol Stream
4.55 out of 5 average rating, 20 reviewsAmazing Summer Pool Awaits You!
Nov 6 – 13
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
4.87 out of 5 average rating, 115 reviewsSoak Up Mid-Century Style in Wrigleyville and Boystown
Sep 14 – 21
Home in Chicago
4.93 out of 5 average rating, 210 reviewsLuxe 6BR House *Trendy Logan Square *Garage Access
Dec 21 – 28
Home in Des Plaines
4.78 out of 5 average rating, 307 reviewsUrban Farmhouse near O'Hare
Sep 7 – 14
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
Jul 9 – 16
Home in Chicago
4.98 out of 5 average rating, 55 reviews2BD/1 BA with summer patio in quiet Roscoe Village
Feb 18 – 25
Home in Chicago
5.0 out of 5 average rating, 5 reviews1-bedroom with full kitchen, washer/dryer inside
Jan 19 – 26
Home in Chicago
4.87 out of 5 average rating, 63 reviewsChicago getaway for two!
Mar 16 – 23
Private house rentals
Home in Chicago
4.98 out of 5 average rating, 50 reviewsCity Cottage in Logan Square-Avondale
Oct 25 – Nov 1
Home in Chicago
4.96 out of 5 average rating, 28 reviewsLakeview Condo
Jan 27 – Feb 3
Home in Chicago
4.97 out of 5 average rating, 75 reviewsCozy/Spacious WFH Family Friendly w Permit Parking
Feb 3 – 10
Home in Chicago
4.98 out of 5 average rating, 61 reviewsVictorian House in Heart of Rogers Park
Sep 14 – 21
Home in Chicago
4.91 out of 5 average rating, 45 reviewsMcFetridge House - Beautiful Private Space #2
Nov 11 – 18
Home in Chicago
4.89 out of 5 average rating, 27 reviewsPrivate Condo in Chicago w/ Parking, Near Evanston
Sep 10 – 17
Home in Berwyn
5.0 out of 5 average rating, 78 reviewsRetro Modern Bungalow | free parking | fire pit
Dec 2 – 9
Home in Chicago
5.0 out of 5 average rating, 48 reviewsCharming 3-BED in Lincoln Park/ Old Town & Parking
Dec 3 – 10
Destinations to explore
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- Rentals with a fire pit North Side
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