Apartment
10.0(413 Reviews)
1 Bedroom
1 Bath
4 Guests
Oceanfront
Parking
Pool
Ocean View
AU $440/Night
7 Nights - AU $3,078
Illinois Winter Rental
10.0
Bed & Breakfast
10.0(26 Reviews)
4 Bedrooms
4 Baths
8 Guests
255.65 ft²
- Parking
Balcony/Terrace
Air Conditioner
Internet
AU $347/Night
7 Nights - AU $2,431
Bed & Breakfast
10.0(530 Reviews)
1 Bedroom
1 Bath
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
AU $368/Night
7 Nights - AU $2,578
Apartment
10.0(233 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
AU $440/Night
7 Nights - AU $3,078
House
10.0(12 Reviews)
3 Bedrooms
1 Bath
6 Guests
1399.31 ft²
- Parking
- Balcony/Terrace
View- Air Conditioner
AU $224/Night
7 Nights - AU $1,565
Condo
10.0(224 Reviews)
2 Bedrooms
2 Baths
9 Guests
Hot Tub- Parking
- Balcony/Terrace
Kitchen
AU $858/Night
7 Nights - AU $6,006
Apartment
10.0(12 Reviews)
1 Bedroom
1 Bath
4 Guests
452.08 ft²
Private Pool- Oceanfront
Breakfast- Parking
AU $165/Night
7 Nights - AU $1,152
Condo
10.0(209 Reviews)
1 Bedroom
1 Bath
5 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
AU $639/Night
7 Nights - AU $4,476
House
10.0(10 Reviews)
2 Bedrooms
2 Baths
4 Guests
1054.86 ft²
- Private Pool
- Pool
- Air Conditioner
- Internet
AU $191/Night
7 Nights - AU $1,339
Apartment
10.0(102 Reviews)
2 Bedrooms
1 Bath
6 Guests
1200 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
AU $489/Night
7 Nights - AU $3,426
Bed & Breakfast
10.0(9 Reviews)
5 Bedrooms
5 Baths
12 Guests
251.88 ft²
- Breakfast
- Parking
- Balcony/Terrace
- View
AU $330/Night
7 Nights - AU $2,313
Condo
10.0(88 Reviews)
2 Bedrooms
1 Bath
4 Guests
1400 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
AU $634/Night
7 Nights - AU $4,439
Why Choose Rent By Owner for your Illinois Winter Rental?
What makes our Winter Rental special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Illinois
How to Book Your Illinois Winter Rental
What's our booking process?
Our platform allows you to browse a curated selection of winter rental. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Common Winter Rental Amenities
What amenities can you expect?
Our Winter Rental are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Illinois, IL
Chicago
Cook County
Chicago
Central Chicago
Downtown Chicago
West Side
The Loop
Jo Daviess County
Lake County
Near North Side
Galena
DeWitt County
Frequently Asked Questions About Illinois Winter Rentals
1. What are the top Winter Rentals in Illinois?
There are a lot of options in Illinois. If you plan on staying in the Illinois area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Winter Rentals in Illinois:
- Peace, quiet and nature at your back door
- Rest, Relax and Renew. Our log cabin experience awaits your arrival.
- Lakeside Cabin in Southern Illinois with Hot Tub!
- Westaway-Spacious Home w/Private Hot Tub, Fireplace, Amazing 1st Floor Layout
- Escape the city to quiet and picturesque Golden Eagle, IL.
- Retreat Cabin in Southern Illinois on Lakefront with an Outdoor Hot Tub
- Galena Oak Glen Getaway near Shopping, Golfing, Hiking
- Picture Perfect Galena Getaway on Golf Course | 4 Bed 4 Bath | Hot Tub & FirePit
- North Woods Lodge Vibes Hot Tub+Fire Pit 3 Seasons Room Galena Territory Retreat
- Remodeled, spacious and bright apartment — near Loyola, beach & subway
2. How many Winter Rentals are available in Illinois?
Currently, the total number of properties listed by RBO in 2026 is over 6827 in the Illinois area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in Illinois.
More Rentals You May Like Near Illinois
Apartment
10.0(7 Reviews)
1 Bedroom
1 Bath
2 Guests
570.49 ft²
- Parking
- View
- Air Conditioner
- Internet
AU $333/Night
7 Nights - AU $2,333
Apartment
10.0(86 Reviews)
1 Bedroom
1 Bath
3 Guests
- Hot Tub
- Parking
Spa- Balcony/Terrace
AU $378/Night
7 Nights - AU $2,648
House
10.0(85 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $368/Night
7 Nights - AU $2,576
Apartment
10.0(83 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $249/Night
7 Nights - AU $1,745
House
10.0(74 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $395/Night
7 Nights - AU $2,767
House
10.0(69 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $452/Night
7 Nights - AU $3,161
House
10.0(65 Reviews)
2 Bedrooms
1 Bath
5 Guests
1200 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
AU $483/Night
7 Nights - AU $3,379
Apartment
10.0(64 Reviews)
1 Bedroom
1 Bath
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $265/Night
7 Nights - AU $1,858
Condo
10.0(63 Reviews)
2 Bedrooms
2 Baths
6 Guests
1500 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
AU $730/Night
7 Nights - AU $5,109
Condo
10.0(60 Reviews)
2 Bedrooms
2 Baths
5 Guests
1200 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $578/Night
7 Nights - AU $4,046
Apartment
10.0(59 Reviews)
1 Bedroom
1 Bath
6 Guests
750 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
AU $422/Night
7 Nights - AU $2,952
Apartment
10.0(58 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $659/Night
7 Nights - AU $4,615
