North Side Cottage Rentals
Cottage
10.0(1 Review)
1 Bedroom
1 Bath
4 Guests
Fireplace/Heating
Balcony/Terrace
Kitchen
Air Conditioner
US $157/Night
7 Nights - US $1,100
Cottage
3 Bedrooms
2 Baths
7 Guests
Internet
Child Friendly
Laundry
Security/Safety
US $235/Night
7 Nights - US $1,647
Apartment
10.0(172 Reviews)
2 Bedrooms
1 Bath
6 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly- Kitchen
US $417/Night
7 Nights - US $2,919
Apartment
10.0(14 Reviews)
1 Bedroom
1 Bath
2 Guests
699.65 ft²
- Internet
- Child Friendly
US $256/Night
7 Nights - US $1,792
Bed & Breakfast
10.0(527 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
Parking- Air Conditioner
US $185/Night
7 Nights - US $1,298
New
Apartment
10.0(2 Reviews)
3 Bedrooms
1 Bath
8 Guests
1250 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $452/Night
7 Nights - US $3,165
Apartment
10.0(4 Reviews)
6 Bedrooms
2 Baths
20 Guests
3498.27 ft²
Private Beach- Fireplace/Heating
Ocean View- Balcony/Terrace
US $922/Night
7 Nights - US $6,456
Condo
9.6(135 Reviews)
3 Bedrooms
1 Bath
5 Guests
1500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $188/Night
7 Nights - US $1,316
Apartment
10.0(4 Reviews)
4 Bedrooms
2 Baths
10 Guests
1205.56 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $413/Night
7 Nights - US $2,893
New
Apartment
9.6(8 Reviews)
1 Bedroom
1 Bath
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Laundry
US $230/Night
7 Nights - US $1,607
Apartment
10.0(4 Reviews)
3 Bedrooms
1 Bath
6 Guests
1001.04 ft²
- Air Conditioner
- Internet
- Child Friendly
US $517/Night
7 Nights - US $3,619
Apartment
8.8(70 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $230/Night
7 Nights - US $1,607
People Visiting North Side Also Like
Why Choose Rent By Owner for your North Side Cottage Rentals?
What makes our Cottage Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for North Side
How to Book Your North Side Cottage Rentals
What's our booking process?
Our platform allows you to browse a curated selection of cottage rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in North Side
Common Cottage Rentals Amenities
What amenities can you expect?
Our Cottage Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in North Side, IL
Sheffield and DePaul
Bucktown
West Bucktown
North Center
Logan Square
Wrigleyville
Avondale
Lakeview
Lincoln Park
Lake View East
Old Town
Old Town Triangle
Frequently Asked Questions About North Side Rental Cottages
1. What are the top Cottages in North Side?
There are a lot of options in North Side. If you plan on staying in the North Side area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Cottages in North Side:
- The Sono Chicago
- Single Family Home! Sleeps 8 Lincoln Park/Lakeview
- Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood
- Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field
- Dramatic Wrigley Loft +PRIVATE Rooftop, Center of Wrigley, Ranked GUEST FAVORITE
- Roscoe Village- Only steps to cute shops & dining! Sleeps 4-6
- Wrigley Field/Lakeview -Entire Home- Large Groups!
- Large 4BR/3BA Safe Old Town Location Walk Everywhere
- Family-friendly, stylish Chicago Apartment in Logan Square
- 5 Bedroom Wrigleyville experience right by stadium
2. How many Cottages are available in North Side?
Currently, the total number of properties listed by RBO in 2026 is over 2 in the North Side area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages in North Side.
More Rentals You May Like Near North Side
House
10.0(3 Reviews)
3 Bedrooms
2 Baths
8 Guests
1001.04 ft²
- Balcony/Terrace
- Pet Friendly
- Parking
- Air Conditioner
US $832/Night
7 Nights - US $5,827
New
Apartment
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $218/Night
7 Nights - US $1,524
Apartment
10.0(2 Reviews)
5 Bedrooms
3 Baths
10 Guests
2497.23 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $1,867/Night
7 Nights - US $13,067
Apartment
10.0(97 Reviews)
2 Bedrooms
1 Bath
6 Guests
1200 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
View
US $350/Night
7 Nights - US $2,447
Apartment
10.0(53 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $510/Night
7 Nights - US $3,570
Apartment
10.0(51 Reviews)
2 Bedrooms
2 Baths
4 Guests
1000 ft²
Hot Tub- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $709/Night
7 Nights - US $4,962
Condo
10.0(36 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $371/Night
7 Nights - US $2,595
Apartment
10.0(33 Reviews)
2 Bedrooms
1 Bath
5 Guests
1000 ft²
- Kitchen
- Parking
- Air Conditioner
- Internet
US $417/Night
7 Nights - US $2,922
Apartment
10.0(29 Reviews)
2 Bedrooms
2 Baths
4 Guests
800 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $562/Night
7 Nights - US $3,932
Apartment
10.0(22 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $401/Night
7 Nights - US $2,807
Apartment
10.0(10 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $319/Night
7 Nights - US $2,235
Apartment
10.0(8 Reviews)
2 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $596/Night
7 Nights - US $4,172
