West Side Resorts
Apartment
10.0(302 Reviews)
4 Bedrooms
2 Baths
8 Guests
1000 ft²
Oceanfront
Fireplace/Heating
Ocean View
View
US $321/Night
7 Nights - US $2,250
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
Bed & Breakfast
9.8(208 Reviews)
1 Bedroom
1 Bath
Breakfast
Kitchen
Air Conditioner
Internet
US $298/Night
7 Nights - US $2,089
New
House
10.0(18 Reviews)
4 Bedrooms
3 Baths
7 Guests
2500 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $539/Night
7 Nights - US $3,770
House
10.0(2 Reviews)
5 Bedrooms
4 Baths
16 Guests
4004.17 ft²
- Fireplace/Heating
- View
- Parking
- Air Conditioner
US $2,234/Night
7 Nights - US $15,637
New
Apartment
10.0(11 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $668/Night
7 Nights - US $4,673
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
New
Apartment
10.0(9 Reviews)
2 Bedrooms
2 Baths
6 Guests
Hot Tub- Fireplace/Heating
Pool- Balcony/Terrace
US $708/Night
7 Nights - US $4,958
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
House
10.0(8 Reviews)
4 Bedrooms
2 Baths
10 Guests
1800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $363/Night
7 Nights - US $2,542
Apartment
10.0(2 Reviews)
1 Bedroom
1 Bath
2 Guests
495.14 ft²
- Fireplace/Heating
- Air Conditioner
- Internet
Child Friendly
US $426/Night
7 Nights - US $2,984
Apartment
10.0(3 Reviews)
2 Bedrooms
2 Baths
6 Guests
800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $347/Night
7 Nights - US $2,428
Why Choose Rent By Owner for your West Side Resorts?
What makes our Resorts 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 Resorts
What's our booking process?
Our platform allows you to browse a curated selection of resorts. 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 Resorts Amenities
What amenities can you expect?
Our Resorts 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
Pulaski Park
Noble Square
Wicker Park
Tri-Taylor
Lower West Side
Near West Side
West Town
West Loop
East Village
University Village / Little Italy
River West
West Loop Gate
West Side Resorts Frequently Asked Questions
1. What are the top Resorts 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 Resorts in West Side:
- Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
- NEW LUXURY PENTHOUSE CONDO
- Entire Below Level Studio w/Private Sauna
- Private Historic Coach House Wicker Park
- 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 Resorts are available in West Side?
Currently, the total number of properties listed by RBO in 2026 is over 1563 in the West Side area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Resorts 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
- Fireplace/Heating
- Parking
- Air Conditioner
- Internet
US $314/Night
7 Nights - US $2,195
New
Apartment
10.0(2 Reviews)
3 Bedrooms
3 Baths
7 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $885/Night
7 Nights - US $6,193
New
Apartment
10.0(2 Reviews)
2 Bedrooms
2 Baths
5 Guests
1147 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $537/Night
7 Nights - US $3,762
Apartment
10.0(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
1500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $375/Night
7 Nights - US $2,627
New
Apartment
10.0(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
550 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $287/Night
7 Nights - US $2,010
Apartment
10.0(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
550 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $271/Night
7 Nights - US $1,895
Apartment
10.0(1 Review)
3 Bedrooms
3 Baths
8 Guests
1500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $1,141/Night
7 Nights - US $7,989
House
10.0(1 Review)
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $597/Night
7 Nights - US $4,182
New
Apartment
10.0(1 Review)
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $332/Night
7 Nights - US $2,324
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $199/Night
7 Nights - US $1,390
New
Condo
9.8(28 Reviews)
3 Bedrooms
2 Baths
6 Guests
1750 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $231/Night
7 Nights - US $1,617
Apartment
9.0(2 Reviews)
3 Bedrooms
3 Baths
7 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $885/Night
7 Nights - US $6,193
