West Side Cottage Rentals
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(4 Reviews)
2 Bedrooms
2 Baths
6 Guests
1399.31 ft²
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
Internet
US $349/Night
7 Nights - US $2,443
Bed & Breakfast
9.8(206 Reviews)
1 Bedroom
1 Bath
Breakfast- Kitchen
- Air Conditioner
- Internet
US $338/Night
7 Nights - US $2,369
Apartment
4 Bedrooms
4 Baths
10 Guests
1600 ft²
- Fireplace/Heating
Balcony/Terrace- Kitchen
- Air Conditioner
US $1,091/Night
7 Nights - US $7,640
Apartment
10.0(3 Reviews)
2 Bedrooms
1 Bath
6 Guests
904.17 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
Parking
US $194/Night
7 Nights - US $1,355
New
House
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $707/Night
7 Nights - US $4,952
House
10.0(2 Reviews)
1 Bedroom
4 Baths
16 Guests
4004.17 ft²
- Fireplace/Heating
View- Parking
- Air Conditioner
US $2,234/Night
7 Nights - US $15,637
New
Apartment
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $677/Night
7 Nights - US $4,738
Apartment
10.0(2 Reviews)
4 Bedrooms
3 Baths
14 Guests
1797.57 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $1,134/Night
7 Nights - US $7,938
Condo
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $457/Night
7 Nights - US $3,196
Apartment
10.0(2 Reviews)
3 Bedrooms
2 Baths
10 Guests
1184.03 ft²
- Fireplace/Heating
- Parking
- Air Conditioner
- Internet
US $651/Night
7 Nights - US $4,555
Apartment
4 Bedrooms
1 Bath
9 Guests
1200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $416/Night
7 Nights - US $2,911
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
Near West Side
West Town
West Loop
East Village
University Village / Little Italy
Lower West Side
Pulaski Park
Noble Square
River West
West Loop Gate
Heart of Chicago
Wicker Park
West Side Cottage Rentals Frequently Asked Questions
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
- 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
- Trendy West Town Flat - 2 bed/1.5 bath with parking
- Quiet Oasis Only Minutes from Downtown - Friendly Neighborhood! by AllSet Turnover
- 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 1558 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
1 Bath
6 Guests
548.96 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $406/Night
7 Nights - US $2,843
New
Apartment
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
Child Friendly
US $381/Night
7 Nights - US $2,666
New
Apartment
2 Bedrooms
1 Bath
7 Guests
750 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $241/Night
7 Nights - US $1,689
Hotel
2 Baths
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $581/Night
7 Nights - US $4,068
New
Hotel
2 Baths
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $501/Night
7 Nights - US $3,509
Hotel
1 Bath
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $494/Night
7 Nights - US $3,460
Hotel
2 Baths
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $478/Night
7 Nights - US $3,349
Condo
10.0(215 Reviews)
2 Bedrooms
2 Baths
9 Guests
Hot Tub- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $631/Night
7 Nights - US $4,414
Condo
10.0(199 Reviews)
1 Bedroom
1 Bath
5 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $395/Night
7 Nights - US $2,764
Apartment
10.0(76 Reviews)
1 Bedroom
1 Bath
3 Guests
- Hot Tub
Spa- Fireplace/Heating
- Balcony/Terrace
US $287/Night
7 Nights - US $2,012
House
10.0(71 Reviews)
2 Bedrooms
1 Bath
5 Guests
880 ft²
Oceanfront- Fireplace/Heating
Ocean View- Balcony/Terrace
US $432/Night
7 Nights - US $3,021
Apartment
10.0(55 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $331/Night
7 Nights - US $2,319
