Condo
10.0(224 Reviews)
2 Bedrooms
2 Baths
9 Guests
Hot Tub
Parking
Balcony/Terrace
Kitchen
CA $840/Night
7 Nights - CA $5,883
West Side Cottage Rentals
10.0
House
10.0(2 Reviews)
5 Bedrooms
4 Baths
16 Guests
4004.17 ft²
- Parking
View
Air Conditioner
Internet
CA $3,077/Night
7 Nights - CA $21,539
Bed & Breakfast
9.8(209 Reviews)
1 Bedroom
1 Bath
Breakfast- Kitchen
- Air Conditioner
- Internet
CA $450/Night
7 Nights - CA $3,152
Condo
10.0(209 Reviews)
1 Bedroom
1 Bath
5 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
CA $626/Night
7 Nights - CA $4,384
Apartment
10.0(2 Reviews)
4 Bedrooms
3 Baths
14 Guests
1797.57 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
CA $1,562/Night
7 Nights - CA $10,934
Apartment
10.0(86 Reviews)
1 Bedroom
1 Bath
3 Guests
- Hot Tub
- Parking
Spa- Balcony/Terrace
CA $371/Night
7 Nights - CA $2,594
Apartment
10.0(2 Reviews)
3 Bedrooms
2 Baths
10 Guests
1184.03 ft²
- Parking
- Air Conditioner
- Internet
Accessibility
CA $896/Night
7 Nights - CA $6,274
Condo
10.0(30 Reviews)
2 Bedrooms
1 Bath
5 Guests
1000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $534/Night
7 Nights - CA $3,738
Apartment
10.0(2 Reviews)
1 Bedroom
1 Bath
2 Guests
495.14 ft²
- Air Conditioner
- Internet
- Accessibility
Wellness Facilities
CA $266/Night
7 Nights - CA $1,861
Apartment
10.0(27 Reviews)
1 Bedroom
1 Bath
4 Guests
- Kitchen
- Air Conditioner
- Internet
Child Friendly
CA $419/Night
7 Nights - CA $2,933
Apartment
10.0(2 Reviews)
4 Bedrooms
4 Baths
10 Guests
1345.49 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
CA $598/Night
7 Nights - CA $4,185
Apartment
10.0(24 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
CA $266/Night
7 Nights - CA $1,862
Why Choose Rent By Owner for your West 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 West Side
How to Book Your West 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.
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 West Side, IL
Near West Side
West Town
West Loop
East Village
University Village / Little Italy
Lower West Side
River West
West Loop Gate
Wicker Park
Pulaski Park
Noble Square
Heart of Chicago
Frequently Asked Questions About West Side Rental Cottages
1. What are the top Cottages in West Side?
There are a lot of options in West Side. If you plan on staying in the West Side area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Cottages in West Side:
- Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
- 3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
- 1F Chicago's Little italy Graystone nearDowntown
- Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
- Private Historic Coach House Wicker Park
- Spacious 3/2 Duplex In Wicker Park Area
- Vibrant 3BR Pilsen Stay Free Parking Near Downtown
- Ukrainian Village 3BR/3BA Private Patio, Parking
- Modern West Loop Gem-City Views & Prime Location 6
- Luxury Modern home minutes from Downtown Chicago
2. How many Cottages are available in West Side?
Currently, the total number of properties listed by RBO in 2026 is over 1600 in the West Side area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages in West Side.
More Rentals You May Like Near West Side
Apartment
10.0(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
904.17 ft²
- Parking
- Air Conditioner
- Internet
- Accessibility
CA $511/Night
7 Nights - CA $3,577
Condo
10.0(20 Reviews)
1 Bedroom
1 Bath
4 Guests
950 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
CA $380/Night
7 Nights - CA $2,660
Condo
10.0(14 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
CA $391/Night
7 Nights - CA $2,738
House
10.0(13 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Parking
- Spa
- Balcony/Terrace
CA $876/Night
7 Nights - CA $6,135
Apartment
10.0(10 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $541/Night
7 Nights - CA $3,788
Apartment
10.0(9 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Parking
Pool- Balcony/Terrace
CA $730/Night
7 Nights - CA $5,108
Apartment
10.0(9 Reviews)
1 Bedroom
1 Bath
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
CA $183/Night
7 Nights - CA $1,282
Apartment
10.0(6 Reviews)
1 Bedroom
1 Bath
2 Guests
350 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
CA $494/Night
7 Nights - CA $3,462
Apartment
10.0(4 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
CA $303/Night
7 Nights - CA $2,124
Apartment
10.0(4 Reviews)
1 Bedroom
1 Bath
2 Guests
450 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
CA $301/Night
7 Nights - CA $2,106
Apartment
10.0(4 Reviews)
1 Bedroom
1 Bath
6 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
CA $287/Night
7 Nights - CA $2,010
Apartment
10.0(4 Reviews)
1 Bedroom
1 Bath
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
CA $218/Night
7 Nights - CA $1,525
