Compare Cottages, Resorts, & Rentals in Near South Side, Chicago, Illinois, USA
About Near South Side Vacation Rentals
There are over 503 amazing vacation rentals available in Near 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 Near 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 Near 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 Near South Side. The average size of places to stay near Near South Side is approximately 905.31 ft², with prices averaging US $359 per night.
Vacation Cottage helps you discover the perfect holiday rental to create lasting travel memories in Near 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 Near South Side, IL
Frequently Asked Questions About Near South Side?
What are the top cottages, summer homes, and lake houses in Near South Side?
- MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba
- Chic 2-Bedroom Townhouse with Rooftop, Free Parking, in Downtown Chicago!
- Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba
- Luxéry Stay "Hollywood" Downtown/McCormick/WinTrust Area
- Luxéry Stay "Chicago" Downtown/McCormick/Wintrust Area
- 2BR South Loop Apt—Walk to Lake, Museums, Aquarium + Pool, Gym, WiFi, & Conv Ct
- Stylish 2BR South Loop Family Unit Near McCormick Place & Soldier Field
- Spacious 6BR Luxury Suite Perfect for Groups Near McCormick Place and Soldier Field
- McCormick 6B/4Ba Luxury Suite for groups/12 guests
- Comfy 3BR Chicago Retreat 420 Friendly Unit Near McCormick Place & Soldier Field
How many rentals, hotels, or resorts are available in Near 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 503 properties listed by Vacation Cottage in the Near 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 Near South Side.
Nearby Neighborhood (7)
| Neighborhood | Property Count |
|---|---|
| Downtown Chicago Rental Cottages and Private Getaways in Chicago, Illinois | 1527 |
| South Loop Rental Cottages and Private Getaways in Chicago, Illinois | 370 |
| Prairie District Rental Cottages and Private Getaways in Chicago, Illinois | 252 |
| Bronzeville Rental Cottages and Private Getaways in Chicago, Illinois | 91 |
| Printers Row Rental Cottages and Private Getaways in Chicago, Illinois | 3802 |
| Ickes Praire Homes Rental Cottages and Private Getaways in Chicago, Illinois | 1999 |
| Chicago Museum Campus Rental Cottages and Private Getaways in Chicago, Illinois | 3119 |
