Apartment holiday rentals in North Side
Find and book unique apartments on Airbnb
Top-rated apartment rentals in North Side
Guests agree: these apartments 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 North Side apartment rentals
Weekly apartment rentals
Apartment in Little Italy
4.96 out of 5 average rating, 127 reviewsPrivate hot tub - King bed suite - Free parking
Apartment in Chicago
4.91 out of 5 average rating, 234 reviewsModern/Spacious 2BR/2BA West Town
Apartment in Chicago
4.98 out of 5 average rating, 289 reviewsSunny Apartment Just 2 Blocks from Wrigley and Boystown
Apartment in Chicago
4.91 out of 5 average rating, 303 reviewsSusie's Space. 2BR easy parking & pet friendly
Apartment in Chicago
4.99 out of 5 average rating, 193 reviewsPets OK | Walk Score 95 | Desk | 1,750ft² |W/D
Apartment in Chicago
4.96 out of 5 average rating, 115 reviewsBest Lincoln Square location. Spacious 2 bedroom
Apartment in Chicago
4.98 out of 5 average rating, 109 reviewsInterior designer duplex 2bd 2bath w/ prvt backyd
Apartment in Chicago
4.9 out of 5 average rating, 194 reviewsA Stones Throw from U Chicago South Campus!
Pet-friendly apartment rentals
Apartment in Evanston
4.77 out of 5 average rating, 570 reviewsSpacious Evanston Unit - Walk to Northwestern U
Apartment in Chicago
4.88 out of 5 average rating, 237 reviews2 King Bed Condo Easy Downtown Free Street Parking
Apartment in Chicago
4.83 out of 5 average rating, 183 reviewsCan't Beat This 2min Walk to Wrigley!
Apartment in Chicago
4.95 out of 5 average rating, 132 reviewsThe Grand Kimball Lodge, Logan Square, Sleeps 14
Apartment in Chicago
4.83 out of 5 average rating, 311 reviewsChic and Charming Vintage Condominium in Lincoln Park
Apartment in Lincoln Park
4.78 out of 5 average rating, 202 reviewsModern Luxury In Old Town - Sleeps 4
Apartment in Chicago
4.79 out of 5 average rating, 109 reviewsSpacious Home, Incredible Lakeview Location
Apartment in Chicago
4.9 out of 5 average rating, 102 reviewsModern designed 2bed/2bath | Heart of Bronzeville!
Apartment rentals with a pool
Apartment in Chicago
4.75 out of 5 average rating, 150 reviewsCentral Downtown Location-Modern 2BR Condo
Apartment in Evanston
4.91 out of 5 average rating, 104 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba
Apartment in Elk Grove Village
4.95 out of 5 average rating, 57 reviewsJust remodeled apartment close to airport and mall
Apartment in Lisle
4.96 out of 5 average rating, 45 reviewsPeaceful Condo in Lisle, Illinois
Apartment in Lombard
4.97 out of 5 average rating, 36 reviewsPond View, Washer Dryer, Non Smoking, Pet Free
Apartment in Chicago
4.78 out of 5 average rating, 18 reviewsLovely condo studio
Apartment in Chicago
4.68 out of 5 average rating, 28 reviews1 bedroom in the heart of downtown Chicago.
Room in Hillside
Lovely Guest Room W private bath rm.
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
- Apartment rentals Chicago
- Apartment rentals Downtown Chicago
- Apartment rentals Milwaukee
- Apartment 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
- Flat 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
- 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
- Cabin Rentals with a Pool United States
- 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
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom