Holiday rentals in North Side
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Top-rated holiday rentals in North Side
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for North Side holiday rentals
Other great holiday rentals in North Side
Guest favourite
Flat in Portage Park
4.95 out of 5 average rating, 110 reviewsComfortable, modern apartment 20 Min from Downtown
Guest favourite
Guest suite in Andersonville
4.96 out of 5 average rating, 322 reviewsGorgeous, cozy 1-bedroom Suite in Andersonville
Guest favourite
Flat in Uptown
4.96 out of 5 average rating, 267 reviewsCozy loft in Chicago's Uptown
Guest favourite
Guest house in Andersonville
4.91 out of 5 average rating, 342 reviewsPrivate, Charming, Coach House Loft in Andersonville
Superhost
Guest suite in Jefferson Park
4.93 out of 5 average rating, 193 reviewsCozy Urban Garden Apartment
Guest favourite
Flat in Roscoe Village
4.95 out of 5 average rating, 241 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Guest favourite
Guest suite in East Rogers Park
4.96 out of 5 average rating, 103 reviews1BR Historic Rogers Park/West Ridge unit- Sleeps 4
Guest favourite
Guest suite in Lake View
4.95 out of 5 average rating, 176 reviews1 mile from Wrigley Field
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- New Buffalo Holiday rentals
- Chicago Holiday rentals
- Rentals with an EV charger North Side
- Rentals with a hot tub North Side
- Waterfront rentals North Side
- Rentals with outdoor seating North Side
- Loft rentals North Side
- Rentals with lake access North Side
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- Rentals with a patio North Side
- Smoking-friendly rentals North Side
- Flat rentals North Side
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- House rentals North Side
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- Rentals with beach access North Side
- Townhouse rentals North Side
- Rentals with breakfast North Side
- Beachfront rentals North Side
- Rentals with a fireplace North Side
- Family-friendly rentals North Side
- Hotel rentals North Side
- Rentals with pools North Side
- Rentals with a firepit North Side
- Rentals with a washing machine and dryer North Side
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