House holiday 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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in North Side
House rentals with a pool
Home in Gary
4.93 out of 5 average rating, 126 reviewsBayless Dune Lodge at West Beach - Indiana Dunes!
Home in Chicago
4.87 out of 5 average rating, 39 reviewsLuxury Cabin in Lakeview
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Home in Plainfield
4.95 out of 5 average rating, 63 reviewsLarge Spanish style Home (w/heated pool)
Home in Schaumburg
4.33 out of 5 average rating, 6 reviewsParadise 4BR w/ Pool & Games
Home in Glen Ellyn
4.94 out of 5 average rating, 17 reviewsGlen Ellyn Home
Home in Lake Forest
4.91 out of 5 average rating, 58 reviewsBeautiful 137 Year Old Farm Home (3night min)
Home in Gary
4.82 out of 5 average rating, 215 reviewsOasis , Near Beach, Hard Rock and Dunes
Weekly house rentals
Home in Chicago
4.98 out of 5 average rating, 176 reviewsThe Evergreen House
Home in Chicago
4.87 out of 5 average rating, 117 reviewsSoak Up Mid-Century Style in Wrigleyville and Boystown
Home in Chicago
4.83 out of 5 average rating, 126 reviewsBucktown Home W/ Free Garage Parking for 2 Cars!
Home in Chicago
4.86 out of 5 average rating, 70 reviewsChicago getaway for two!
Home in Chicago
4.91 out of 5 average rating, 92 reviewsBoho Chic Coach House 30Min to downtown W/ Parking
Home in Chicago
4.97 out of 5 average rating, 31 reviewsLakeview Condo
Home in Chicago
5.0 out of 5 average rating, 6 reviews1-bedroom with full kitchen, washer/dryer inside
Home in Chicago
5.0 out of 5 average rating, 13 reviewsHidden Gem on the CHI north side
Private house rentals
Home in Chicago
4.98 out of 5 average rating, 52 reviewsCity Cottage in Logan Square-Avondale
Home in Berwyn
4.99 out of 5 average rating, 84 reviewsRetro Modern Bungalow | free parking | fire pit
Home in Chicago
4.98 out of 5 average rating, 66 reviewsVictorian House in Heart of Rogers Park
Home in Chicago
4.99 out of 5 average rating, 98 reviewsHuge Sunlit Gem, Free Parking, No Cleaning Fee
Home in Chicago
4.92 out of 5 average rating, 25 reviewsNorthside Chicago Getaway
Home in Chicago
5.0 out of 5 average rating, 53 reviewsCharming 3-BED in Lincoln Park/ Old Town & Parking
Home in Chicago
4.85 out of 5 average rating, 84 reviewsFree parking, close to public transit, dining
Home in Chicago
5.0 out of 5 average rating, 89 reviewsAndersonville/ Cozy 3b 3b House / 99 walk score
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
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- Townhouse rentals North Side
- Waterfront rentals North Side
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- Loft rentals North Side
- Smoking-friendly rentals North Side
- Rentals with beach access North Side
- Hotel rentals North Side
- Rentals with pools North Side
- Rentals with a firepit North Side
- Fitness-friendly rentals North Side
- Bed and breakfasts North Side
- Rentals with an EV charger North Side
- Guest house rentals North Side
- Rentals with lake access North Side
- Beachfront rentals North Side
- Rentals with a fireplace North Side
- Rentals with a hot tub North Side
- Apartment rentals North Side
- Rentals with a washing machine and dryer North Side
- Rentals with breakfast North Side
- Monthly Rentals North Side
- Family-friendly rentals North Side
- Rentals with outdoor seating North Side
- Private suite rentals North Side
- Pet-friendly rentals North Side
- Flat rentals North Side
- Rentals with a patio North Side
- Rentals with a balcony North Side
- Yurt Rentals United States
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- Holiday Caravans United Kingdom
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- Farm Houses United States
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- Cabin Rentals Australia
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- Holiday Chalets United Kingdom
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