Chicago 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
1 Bedroom
1 Bath
4 Guests
1100 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $110/Night
7 Nights - US $772
Cottage
3 Bedrooms
2 Baths
7 Guests
Internet
Child Friendly
Laundry
Security/Safety
US $235/Night
7 Nights - US $1,647
Cottage
10.0(6 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
Pet Friendly- Kitchen
Parking
US $214/Night
7 Nights - US $1,496
Cottage
5.0(2 Reviews)
1 Bedroom
1 Bath
4 Guests
- Kitchen
- Air Conditioner
- Child Friendly
TV
US $153/Night
7 Nights - US $1,071
New
House
10.0(1 Review)
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $762/Night
7 Nights - US $5,334
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
House
7.0(102 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $143/Night
7 Nights - US $1,004
New
Apartment
10.0(1 Review)
2 Bedrooms
1 Bath
3 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $247/Night
7 Nights - US $1,727
Apartment
10.0(12 Reviews)
1 Bedroom
1 Bath
4 Guests
452.08 ft²
Private Pool
Oceanfront- Fireplace/Heating
Pool
US $117/Night
7 Nights - US $819
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $136/Night
7 Nights - US $950
Apartment
10.0(8 Reviews)
2 Bedrooms
1 Bath
4 Guests
914.93 ft²
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $618/Night
7 Nights - US $4,329
People Visiting Chicago Also Like
Why Choose Rent By Owner for your Chicago 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 Chicago
How to Book Your Chicago 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 Chicago
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 Chicago, IL
Chicago
Central Chicago
Downtown Chicago
West Side
The Loop
Near North Side
North Side
River North
South Loop
South Side
Far North Side
Near South Side
Frequently Asked Questions About Chicago Rental Cottages
1. What are the top Cottages in Chicago?
There are a lot of options in Chicago. If you plan on staying in the Chicago area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Cottages in Chicago:
- Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
- Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach
- NEW LUXURY PENTHOUSE CONDO
- Great Location-Beautiful Friendly Andersonville Neighborhood
- Single Family Home! Sleeps 8 Lincoln Park/Lakeview
- Magic Factory Loft 2West
- NEW LUXURY CONDO WITH PATIO DECK
- Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood
- Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
- 4BR Old Town Chicago Loft | Walk to Wells St
2. How many Cottages are available in Chicago?
Currently, the total number of properties listed by RBO in 2026 is over 5 in the Chicago area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages in Chicago.
More Rentals You May Like Near Chicago
New
Apartment
4 Bedrooms
4 Baths
10 Guests
1600 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,128/Night
7 Nights - US $7,897
Apartment
10.0(5 Reviews)
3 Bedrooms
2 Baths
6 Guests
1496.18 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $686/Night
7 Nights - US $4,800
New
Apartment
5 Bedrooms
2 Baths
12 Guests
23681 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $1,119/Night
7 Nights - US $7,831
Apartment
10.0(5 Reviews)
3 Bedrooms
2 Baths
5 Guests
1345.49 ft²
- Balcony/Terrace
- Pet Friendly
- Parking
- Air Conditioner
US $284/Night
7 Nights - US $1,991
New
Apartment
4 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $1,005/Night
7 Nights - US $7,032
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
New
House
4 Bedrooms
5 Baths
10 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $906/Night
7 Nights - US $6,340
New
Apartment
2 Bedrooms
1 Bath
4 Guests
754 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $505/Night
7 Nights - US $3,532
New
Apartment
2 Bedrooms
1 Bath
5 Guests
849 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Internet
US $497/Night
7 Nights - US $3,476
Apartment
4 Bedrooms
1 Bath
9 Guests
1200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $369/Night
7 Nights - US $2,583
New
Apartment
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $260/Night
7 Nights - US $1,823
New
Apartment
3 Bedrooms
2 Baths
5 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $151/Night
7 Nights - US $1,059
