Compare Cottages, Resorts, & Rentals in South Side, Illinois, USA
About South Side Vacation Rentals
There are over 554 amazing vacation rentals available in South Side. Choose from a variety of options including villas, hotels, and other rental properties. Explore a vast selection of luxury amenities at unbeatable prices, providing you with the ideal spot for your next getaway. Life is Better at the Cottage with Vacation Cottage, where you can discover fantastic stays in South Side.
Vacation Cottage offers numerous last-minute deals on villas, hotels, and rentals, both near you and across the globe. Whether you need accommodations for a group or event, such as a hotel or vacation rental (including cabins and private luxury villas), let us assist you. With Vacation Cottage in South Side, you can easily compare options from multiple suppliers with just a click to find the perfect price point, amenities, and style of stay for you. Whether you're seeking group discounts, private pools, hot tubs, pet-friendly options, or spacious master suite bedrooms with open-air showers, you can find it all with Vacation Cottage vacation rentals, resorts, and Airbnb-style properties in South Side. The average size of places to stay near South Side is approximately 799.82 ft², with prices averaging US $459 per night.
Vacation Cottage helps you discover the perfect holiday rental to create lasting travel memories in South Side. Prices listed often feature discounts compared to rack rates. Simply search for your destination and secure your ideal place to stay today.
Find Vacation Cottage Rentals in these Cities and Neighborhoods South Side, IL
Frequently Asked Questions About South Side?
What are the top cottages, summer homes, and lake houses in South Side?
- Chic 2-Bedroom Townhouse with Rooftop, Free Parking, in Downtown Chicago!
- Spacious 3BR Corner Family Oasis Near McCormick Place & Soldier Field
- McCormick Apt 3BR Corner Oasis Near Soldier Field & Museum Campus
- Walkable 2BR Apartment in Chicago South Loop with Optional Parking and Gym Access Near McCormick Place, Museum Campus & Lakefront
- Spacious 3BR · Bronzeville/South Loop · Sleeps 8
- Cozy 2BR South Loop Condo with Optional Parking and Gym Near McCormick Place, Public Transit & City Hotspots
- McCormick Place Patio skyline 2b/2b with optional Parking for up to 6 people
- Spacious 2BR South Loop Suite with Skyline View, Optional Parking and Gym Access Close to McCormick Place, Grant Park, Museum Campus & CTA Lines
- South Loop · 3 Kings · Steps from McCormick Place
- South Loop Chicago 3BR Corner Suite Near Museum Campus & Millennium Park
How many rentals, hotels, or resorts are available in South Side?
Vacation Cottage consistently updates its selection, offering a blend of new options alongside well-established accommodations in prime locations. Currently, there are over 554 properties listed by Vacation Cottage in the South Side area for the year 2026, with this number increasing daily. By aggregating listings from various websites and travel providers, Vacation Cottage ensures a diverse array of choices for the best luxury stays in South Side.
Nearby Neighborhood (11)
| Neighborhood | Property Count |
|---|---|
| Downtown Chicago Rental Cottages and Private Getaways in Chicago, Illinois | 838 |
| The Loop Rental Cottages and Private Getaways in Chicago, Illinois | 387 |
| Near West Side Rental Cottages and Private Getaways in Chicago, Illinois | 185 |
| South Loop Rental Cottages and Private Getaways in Chicago, Illinois | 137 |
| Near South Side Rental Cottages and Private Getaways in Chicago, Illinois | 131 |
| West Loop Rental Cottages and Private Getaways in Chicago, Illinois | 120 |
| Prairie District Rental Cottages and Private Getaways in Chicago, Illinois | 99 |
| Lower West Side Rental Cottages and Private Getaways in Chicago, Illinois | 2284 |
| Chinatown Rental Cottages and Private Getaways in Chicago, Illinois | 3211 |
| Printers Row Rental Cottages and Private Getaways in Chicago, Illinois | 4131 |
| Chicago Museum Campus Rental Cottages and Private Getaways in Chicago, Illinois | 3309 |
