Discover winter rentals South Loop - We found 150 exact matches
About South Loop Winter Rental on Vacation Cottage
At Vacation Cottage, we showcase a diverse array of accommodations in South Loop, IL perfect for your winter retreat or seasonal escape. Our listings encompass hotels, private vacation homes, cabins, condos, villas, resorts, and pet-friendly apartments, ensuring travelers find their ideal accommodation. Vacation Cottage's winter vacation homes boast premier amenities such as Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.
Whether you're seeking to escape the snow or embrace it, Vacation Cottage facilitates your connection to the finest cabins, bungalows, lodges, rent-by-owner homes, and the best accommodations in both sunny retreats and ski resorts. Vacation Cottage ensures your winter getaway becomes an unforgettable experience.
Vacation Cottage presents luxury options for travelers seeking to rent a place in South Loop. To access these benefits and book your winter vacation home, simply utilize the Vacation Cottage filter option. Enter your travel dates, refine your search with filters for property type and amenities, then choose from our extensive list of exceptional winter vacation rentals hassle-free. Our interactive map further enhances your experience, allowing you to explore destinations worldwide or within South Loop and unlock incredible deals. Life is Better at the Cottage with Vacation Cottage.
Frequently Asked Questions About South Loop Winter Rentals
What are the top rated Winter Rentals in South Loop?
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 Winter Rentals in South Loop:
- Downtown Penthouse Lake Views #1|Gym, Parking+Pool
- McCormick Place 2b/2b family unit with optional parking for up to 8 guests
- McCormick 6B/4Ba Luxury Suite for groups/12 guests
- McCormick Place Skyline view 2b/2b unit with optional parking for up to 8 guests
- McCormick 6B/3Ba Luxury Suite for groups/12 guests
- Luxurious McCormick Place 6 bed/3 bath Suite for groups with optional parking
- The Wheeler Mansion
- McCormick Place 3b/2b family oasis with optional parking for up to 10 guests
- Spacious and luxurious apartment/sleeps 10 and with optional parking
- McCormick 3B/2Ba Corner Oasis for up to 10 guests
How much does it cost to rent a place to stay near South Loop in the wintertime?
The average cost for winter rentals in South Loop is $466 per night. Vacation Cottage has a wide list of great winter places to stay near South Loop that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in South Loop that allow pets?
Yes, here are the top cottage/chalet rentals in South Loop that allow you to bring your pet or dog:
- Downtown Penthouse Lake Views #1|Gym, Parking+Pool
- Luxéry Stay Chicago - Themed Units! Close to Downtown, McCormick Place & Wintrust Arena
- The Wheeler Mansion
- McCormick Place 2b/2b family unit with optional parking for up to 8 guests
See all pet-friendly vacation rentals in South Loop on Vacation Cottage
Do you have any winter rentals in South Loop that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in South Loop to find what works for you.
Are there winter accommodations in South Loop that have indoor swimming pools?
As of 2025, the data from Vacation Cottage shows that there are over 150 private swimming pools or indoor pools accommodations near South Loop along with other great amenities.
Do any winter holiday rentals in South Loop have hot tubs?
About 150 holiday rentals in South Loop boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in South Loop?
Yes, there are many luxury places to stay in South Loop for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near South Loop with all the best amenities for your next trip.
