South Loop Cottage Rentals

Compare Cottages, Resorts, & Rentals in South Loop, Chicago, Illinois, USA

New Budget-Friendly Room| Free Coffee | Downtown
New
2 Bedrooms 1 Guest
|
9.2 (1061 Reviews)
1 Bedroom 2 Guests
New Budget-Friendly Room| Free Coffee | Downtown
New
2 Bedrooms 1 Guest
From US $245 per night
|
9.2 (1001 Reviews)
1 Bedroom 2 Guests
New Budget-Friendly Room| Free Coffee | Downtown
New
2 Bedrooms 1 Guest
|
9.2 (768 Reviews)
1 Bedroom 2 Guests
New Budget-Friendly Room| Free Coffee | Downtown
New
2 Bedrooms 1 Guest
|
10.0 (1 Review)
3 Bedrooms 8 Guests
10.0 (26 Reviews)
1 Bedroom 6 Guests
10.0 (10 Reviews)
1 Bedroom 6 Guests
|
10.0 (1 Review)
1 Bedroom 8 Guests
10.0 (4 Reviews)
1 Bedroom 4 Guests
10.0 (2 Reviews)
1 Bedroom 4 Guests
10.0 (2 Reviews)
1 Bedroom 4 Guests
|
10.0 (1 Review)
1 Bedroom 8 Guests
10.0 (2 Reviews)
2 Bedrooms 5 Guests
10.0 (2 Reviews)
2 Bedrooms 6 Guests
10.0 (1 Review)
2 Bedrooms 6 Guests
|
9.0 (1010 Reviews)
1 Bedroom 2 Guests
From US $724 per night
|
9.0 (4 Reviews)
1 Bedroom 2 Guests
|
8.8 (2215 Reviews)
1 Bedroom 2 Guests
From US $211 per night
|
8.7 (6 Reviews)
1 Bedroom 8 Guests
6.0 (1 Review)
2 Bedrooms 1 Guest
4.0 (1 Review)
2 Bedrooms 6 Guests
4.0 (1 Review)
2 Bedrooms 8 Guests
From US $561 per night
New
2 Bedrooms 6 Guests

About South Loop Vacation Rentals

There are over 517 amazing vacation rentals available in South Loop. 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 Loop.

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 Loop, 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 Loop. The average size of places to stay near South Loop is approximately 894.51 ft², with prices averaging US $381 per night.

Vacation Cottage helps you discover the perfect holiday rental to create lasting travel memories in South Loop. Prices listed often feature discounts compared to rack rates. Simply search for your destination and secure your ideal place to stay today.

Frequently Asked Questions About South Loop?

What are the top cottages, summer homes, and lake houses in South Loop?

How many rentals, hotels, or resorts are available in South Loop?

Vacation Cottage consistently updates its selection, offering a blend of new options alongside well-established accommodations in prime locations. Currently, there are over 517 properties listed by Vacation Cottage in the South Loop 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 Loop.

Nearby Neighborhood (7)

Neighborhood Property Count
Downtown Chicago Rental Cottages and Private Getaways in Chicago, Illinois 1548
The Loop Rental Cottages and Private Getaways in Chicago, Illinois 717
Near South Side Rental Cottages and Private Getaways in Chicago, Illinois 351
Prairie District Rental Cottages and Private Getaways in Chicago, Illinois 251
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