Illinois Winter Rental
Cabin
10.0(439 Reviews)
1 Bedroom
1 Bath
3 Guests
900 ft²
Hot Tub
Fireplace/Heating
Balcony/Terrace
Kitchen
US $170/Night
7 Nights - US $1,187
Bed & Breakfast
10.0(24 Reviews)
4 Bedrooms
4 Baths
8 Guests
255.64 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
Breakfast
US $247/Night
7 Nights - US $1,729
Bed & Breakfast
10.0(517 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
Parking
Air Conditioner
US $339/Night
7 Nights - US $2,375
Cabin
10.0(412 Reviews)
1 Bedroom
1 Bath
3 Guests
500 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $139/Night
7 Nights - US $974
House
10.0(12 Reviews)
3 Bedrooms
1 Bath
6 Guests
1399.31 ft²
- Fireplace/Heating
- Balcony/Terrace
View- Parking
US $159/Night
7 Nights - US $1,113
House
10.0(403 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $164/Night
7 Nights - US $1,147
Apartment
10.0(12 Reviews)
1 Bedroom
1 Bath
4 Guests
452.08 ft²
Private Pool
Oceanfront- Fireplace/Heating
Pool
US $117/Night
7 Nights - US $819
House
10.0(372 Reviews)
2 Bedrooms
2 Baths
4 Guests
2100 ft²
- Hot Tub
- Fireplace/Heating
Ocean View- Balcony/Terrace
US $233/Night
7 Nights - US $1,632
Bed & Breakfast
10.0(8 Reviews)
5 Bedrooms
5 Baths
12 Guests
251.88 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Breakfast
US $222/Night
7 Nights - US $1,554
House
10.0(358 Reviews)
2 Bedrooms
1 Bath
6 Guests
1000 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly
US $173/Night
7 Nights - US $1,212
Apartment
10.0(7 Reviews)
1 Bedroom
1 Bath
2 Guests
570.49 ft²
- Fireplace/Heating
- View
- Pet Friendly
- Parking
US $213/Night
7 Nights - US $1,488
Cabin
10.0(283 Reviews)
2 Bedrooms
1 Bath
4 Guests
790 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $214/Night
7 Nights - US $1,495
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.
Explore and book the perfect rental in Illinois
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
Jo Daviess County
The Loop
Lake County
Near North Side
Galena
North Side
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:
- 52nd Floor MagMile Penthouse Views Fireplace Pool
- Westaway-Spacious Home w/Private Hot Tub, Fireplace, Amazing 1st Floor Layout
- Escape! Hot Tub, Fire Pit, 3 Decks, WiFi, Pool Table
- Charming 3BR/3BA With Hot Tub, Fireplace & Pool Table
- WIFI FLEXCATION & RELAXATION! Cozy fireplace, reading, movies, fire pit & more!
- Galena Oak Glen Getaway near Shopping, Golfing, Hiking
- Relaxing escape or fishing getaway! Central location for hiking, wineries, fun
- 55th Floor Penthouse with Award-Winning Views
- Picture Perfect Galena Getaway on Golf Course | 4 Bed 4 Bath | Hot Tub & FirePit
- Welcome to your Galena Get Away!
2. How many Winter Rentals are available in Illinois?
Currently, the total number of properties listed by RBO in 2026 is over 6579 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
House
10.0(5 Reviews)
3 Bedrooms
2 Baths
8 Guests
1496.18 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $228/Night
7 Nights - US $1,597
Cabin
10.0(248 Reviews)
1 Bedroom
2 Baths
4 Guests
800 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $184/Night
7 Nights - US $1,288
House
10.0(218 Reviews)
2 Bedrooms
1 Bath
6 Guests
2064 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $175/Night
7 Nights - US $1,224
House
10.0(217 Reviews)
2 Bedrooms
1 Bath
6 Guests
1901 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $184/Night
7 Nights - US $1,286
Cabin
10.0(202 Reviews)
2 Bedrooms
2 Baths
6 Guests
1100 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $194/Night
7 Nights - US $1,359
Cottage
10.0(169 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $196/Night
7 Nights - US $1,372
Cabin
10.0(167 Reviews)
2 Bedrooms
1 Bath
4 Guests
900 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $194/Night
7 Nights - US $1,360
Cabin
10.0(151 Reviews)
2 Bedrooms
1 Bath
4 Guests
900 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $198/Night
7 Nights - US $1,385
House
10.0(139 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $295/Night
7 Nights - US $2,068
House
10.0(135 Reviews)
1 Bedroom
1 Bath
2 Guests
900 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $95/Night
7 Nights - US $668
House
10.0(126 Reviews)
2 Bedrooms
1 Bath
4 Guests
700 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $261/Night
7 Nights - US $1,830
Cabin
10.0(119 Reviews)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $254/Night
7 Nights - US $1,776
