Apartment holiday rentals in North Side
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Top-rated apartment rentals in North Side
Guests agree: these apartments are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for North Side apartment rentals
Weekly apartment rentals
Flat in Logan Square
4.87 out of 5 average rating, 488 reviewsLogan Square Studio
Flat in Andersonville
4.96 out of 5 average rating, 257 reviewsSunny, Cozy, Colorful Andersonville
Flat in Chicago
4.99 out of 5 average rating, 183 reviewsNW Chicago Apartment in Safe Neighborhood
Flat in Logan Square
4.89 out of 5 average rating, 346 reviewsSunny Logan Square Artists' home
Flat in Irving Park
4.86 out of 5 average rating, 106 reviews⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
Flat in Logan Square
4.97 out of 5 average rating, 259 reviewsLogan Square 2nd Floor Chicago Victorian
Flat in Lincoln Park
4.98 out of 5 average rating, 304 reviewsRedesigned Lower Level Studio in Historic Building
Flat in Wrigleyville
4.8 out of 5 average rating, 387 reviews'Secret Garden' Apartment in Wrigleyville
Private apartment rentals
Flat in Chicago
4.86 out of 5 average rating, 328 reviewsThe Avondale Garden Unit
Flat in West Loop
4.87 out of 5 average rating, 220 reviewsGarden Apartment in the Historic Heart of the City
Flat in Jefferson Park
4.97 out of 5 average rating, 170 reviewsElegant & Clean Cottage Apt 20 minutes from O’Hare
Flat in Chicago
4.87 out of 5 average rating, 276 reviewsHistoric Old Town Flat - Minutes from Downtown!
Flat in Lake View
4.87 out of 5 average rating, 243 reviewsWELCOME TO NANCY'S PAD!
Flat in West Town
4.95 out of 5 average rating, 365 reviewsA Vintage Pink House in the Heart of Chicago
Flat in Avondale
4.82 out of 5 average rating, 116 reviewsCozy Avondale apt right by Belmont blue line stop
Flat in Lake View
4.88 out of 5 average rating, 192 reviewsComfort zone
Apartment rentals with a hot tub
Flat in West Town
4.88 out of 5 average rating, 398 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Flat in Near South Side
4.87 out of 5 average rating, 160 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Flat in Berwyn
4.91 out of 5 average rating, 207 reviews“Dream slice of urban homesteading.”
Flat in West Loop
4.87 out of 5 average rating, 106 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
Flat in Logan Square
4.92 out of 5 average rating, 37 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Flat in West Rogers Park
4.79 out of 5 average rating, 24 reviewsSpacious Beautiful Condo
Flat in Belmont Cragin
5.0 out of 5 average rating, 31 reviewsBelmont Pleasures - hot tub / arcade gaming room
Flat in Streeterville
5.0 out of 5 average rating, 11 reviewsLake, City, & River View Condo
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
- Serviced apartment rentals United States
- Flat rentals United States
- Flat rentals Chicago
- Flat rentals Downtown Chicago
- Flat rentals Milwaukee
- Flat rentals Illinois
- Rentals with outdoor seating North Side
- Rentals with beach access North Side
- House rentals North Side
- Guest house rentals North Side
- Rentals with a balcony North Side
- Loft rentals North Side
- Fitness-friendly rentals North Side
- Waterfront rentals North Side
- Monthly Rentals North Side
- Townhouse rentals North Side
- Rentals with a patio North Side
- Smoking-friendly rentals North Side
- Rentals with lake access North Side
- Rentals with a firepit North Side
- Rentals with a hot tub North Side
- Rentals with an EV charger North Side
- Apartment rentals North Side
- Family-friendly rentals North Side
- Rentals with breakfast North Side
- Hotel rentals North Side
- Rentals with pools North Side
- Rentals with a washing machine and dryer North Side
- Pet-friendly rentals North Side
- Family-friendly rentals North Side
- Beachfront rentals North Side
- Rentals with a fireplace North Side
- Bed and breakfasts North Side
- Private suite rentals North Side
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
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- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
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- Pet-Friendly Vacation Rentals United States
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- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom