West Side Cottage Rentals
Apartment
10.0(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
Fireplace/Heating
Kitchen
Air Conditioner
Internet
CA $306/Night
7 Nights - CA $2,139
Apartment
10.0(8 Reviews)
1 Bedroom
1 Bath
2 Guests
495.14 ft²
Pet Friendly
Parking- Air Conditioner
- Internet
CA $258/Night
7 Nights - CA $1,808
Bed & Breakfast
9.8(206 Reviews)
1 Bedroom
1 Bath
Breakfast- Kitchen
- Air Conditioner
- Internet
CA $377/Night
7 Nights - CA $2,639
New
House
4 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
Child Friendly
CA $1,060/Night
7 Nights - CA $7,417
Apartment
10.0(4 Reviews)
2 Bedrooms
2 Baths
6 Guests
1399.31 ft²
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
CA $482/Night
7 Nights - CA $3,374
New
Apartment
2 Bedrooms
2 Baths
6 Guests
646 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
CA $816/Night
7 Nights - CA $5,710
Apartment
10.0(3 Reviews)
2 Bedrooms
1 Bath
6 Guests
904.17 ft²
- Fireplace/Heating
Balcony/Terrace- Pet Friendly
- Parking
CA $267/Night
7 Nights - CA $1,871
New
Condo
3 Bedrooms
2 Baths
5 Guests
1300 ft²
- Fireplace/Heating
Pool- Balcony/Terrace
- Pet Friendly
CA $533/Night
7 Nights - CA $3,735
House
10.0(2 Reviews)
1 Bedroom
4 Baths
16 Guests
4004.17 ft²
- Fireplace/Heating
View- Parking
- Air Conditioner
CA $3,085/Night
7 Nights - CA $21,597
New
Apartment
2 Bedrooms
3 Baths
6 Guests
1300 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
CA $520/Night
7 Nights - CA $3,638
Apartment
10.0(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
645.83 ft²
- Fireplace/Heating
- Parking
- Air Conditioner
- Internet
CA $942/Night
7 Nights - CA $6,596
New
Apartment
2 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
CA $511/Night
7 Nights - CA $3,579
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.
Explore and book the perfect rental in West 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 West Side, IL
West Town
Near West Side
East Village
West Loop
University Village / Little Italy
Lower West Side
Wicker Park
River West
Pulaski Park
Noble Square
Heart of Chicago
West Loop Gate
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
- Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath
- Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
- Spacious 4-Level/4-Bedroom Townhouse in West Loop
- Spacious 3/2 Duplex In Wicker Park Area
- Ukrainian Village 3BR/3BA Private Patio, Parking
- Vibrant 3BR Pilsen Stay Free Parking Near Downtown
- Modern West Loop Gem-City Views & Prime Location 6
2. How many Cottages are available in West Side?
Currently, the total number of properties listed by RBO in 2026 is over 1550 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)
1 Bedroom
2 Baths
10 Guests
1184.03 ft²
- Fireplace/Heating
- Parking
- Air Conditioner
- Internet
CA $899/Night
7 Nights - CA $6,291
New
Condo
2 Bedrooms
1 Bath
3 Guests
Hot Tub- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $246/Night
7 Nights - CA $1,721
New
Apartment
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
Laundry
CA $172/Night
7 Nights - CA $1,202
Apartment
2 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $159/Night
7 Nights - CA $1,112
Condo
10.0(210 Reviews)
2 Bedrooms
2 Baths
9 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $871/Night
7 Nights - CA $6,096
Condo
10.0(197 Reviews)
1 Bedroom
1 Bath
5 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $545/Night
7 Nights - CA $3,817
Apartment
10.0(75 Reviews)
1 Bedroom
1 Bath
3 Guests
- Hot Tub
Spa- Fireplace/Heating
- Balcony/Terrace
CA $402/Night
7 Nights - CA $2,816
House
10.0(70 Reviews)
2 Bedrooms
1 Bath
5 Guests
880 ft²
Oceanfront- Fireplace/Heating
Ocean View- Balcony/Terrace
CA $596/Night
7 Nights - CA $4,172
Apartment
10.0(51 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
CA $444/Night
7 Nights - CA $3,106
Condo
10.0(26 Reviews)
2 Bedrooms
1 Bath
5 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
CA $469/Night
7 Nights - CA $3,280
Apartment
10.0(24 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $635/Night
7 Nights - CA $4,447
Condo
10.0(17 Reviews)
1 Bedroom
1 Bath
4 Guests
950 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $575/Night
7 Nights - CA $4,022
