South Loop Cottage Rentals & Holiday Homes
Find the best cottages in South Loop - We found 580 exact matches
About South Loop Cottage Rentals on SunSkiResorts
Searching for cottages to rent near South Loop? SunSki features more than 580 cottages that are perfect for your next trip. Escape the snow and slopes and discover luxury cottage rentals just a few miles away from the lake or beach. These cottage rentals in South Loop offer hot baths, are kid-friendly & family-friendly, and are situated near top local attraction spots, ensuring guests have the best travel experience possible. SunSki’s cottage listings come in all shapes and sizes, catering to large groups, friends, or couples in South Loop.
Planning to travel to the lakeside, beach, or mountain area? SunSki’s cottage rentals offer a wide selection, providing direct access to the owners of these cottage rentals and offering you the best opportunity to find a good price.
SunSki boasts of 580 holiday cottages and places to stay in South Loop. The site provides unique Airbnb, VRBO, ski-style cottages to fit your trip or getaway with your friends and family. Whether it's a weekend getaway, spring break, summer vacation, or annual holiday, all fit within your budget.
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Frequently Asked Questions About South Loop Rental Cottages
There are a lot of options in South Loop. If you plan on staying in the South Loop area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in South Loop:
- Downtown 3bd Penthouse| Lake Mich VIEWS +gym
- Spacious 2BR in Chicago Near McCormick Sleeps 8
- Charming 2BR Unit Near McCormick Place & Millennium Park
- Sleep 14 | Downtown, Vintage 5bd/2ba (gym+patio)
- McCormick Place Modern 2BR Loft in Downtown Chicago Michigan Avenue with Optional Parking Near Soldier Field
- Modern 3BR Near McCormick & South Loop
- South Loop 3BD 2BA Condo with Balcony and Parking
- Central 2BR South Loop Location with Optional Parking & Gym Access Near McCormick Place, Shedd Aquarium & Navy Pier
- 29th Floor 2BR Grant Park Suite with Balcony, Gym
- Skyline 2BR 2BA in South Loop Near Museums & McCormick Place
- Cozy Downtown MICH AVE #7 | gym+rooftop
- Chic Spacious 3BR South Loop Apartment Near McCormick Place, Roosevelt CTA & Shopping Area in Chicago
- The Wheeler Mansion
- Chic 2-Bedroom Townhouse with Rooftop, Free Parking, in Downtown Chicago!
See all pet-friendly vacation rentals in South Loop on SunSkiResorts










