Illinois Winter Rental
Cabin
10.0(434 Reviews)
1 Bedroom
1 Bath
3 Guests
900 ft²
Hot Tub
Fireplace/Heating
Balcony/Terrace
Kitchen
CA $244/Night
7 Nights - CA $1,706
Bed & Breakfast
10.0(24 Reviews)
4 Bedrooms
4 Baths
8 Guests
255.64 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
Breakfast
CA $338/Night
7 Nights - CA $2,367
Bed & Breakfast
10.0(510 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
Parking
Air Conditioner
CA $225/Night
7 Nights - CA $1,574
Cabin
10.0(411 Reviews)
1 Bedroom
1 Bath
3 Guests
500 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $191/Night
7 Nights - CA $1,333
House
10.0(12 Reviews)
3 Bedrooms
1 Bath
6 Guests
1399.31 ft²
- Fireplace/Heating
- Balcony/Terrace
View- Parking
CA $218/Night
7 Nights - CA $1,523
House
10.0(400 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $226/Night
7 Nights - CA $1,581
Apartment
10.0(12 Reviews)
1 Bedroom
1 Bath
4 Guests
452.08 ft²
Private Pool
Oceanfront- Fireplace/Heating
Pool
CA $160/Night
7 Nights - CA $1,121
House
10.0(370 Reviews)
2 Bedrooms
2 Baths
4 Guests
2100 ft²
- Hot Tub
- Fireplace/Heating
Ocean View- Balcony/Terrace
CA $319/Night
7 Nights - CA $2,234
Bed & Breakfast
10.0(8 Reviews)
5 Bedrooms
5 Baths
12 Guests
251.88 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Breakfast
CA $304/Night
7 Nights - CA $2,127
House
10.0(351 Reviews)
2 Bedrooms
1 Bath
6 Guests
1000 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly
CA $226/Night
7 Nights - CA $1,581
Apartment
10.0(7 Reviews)
1 Bedroom
1 Bath
2 Guests
570.49 ft²
- Fireplace/Heating
- View
- Pet Friendly
- Parking
CA $291/Night
7 Nights - CA $2,037
Cabin
10.0(281 Reviews)
2 Bedrooms
1 Bath
4 Guests
790 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $289/Night
7 Nights - CA $2,020
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
North Side
Near North Side
Lake County
Galena
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 6632 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
CA $312/Night
7 Nights - CA $2,186
Cabin
10.0(244 Reviews)
1 Bedroom
2 Baths
4 Guests
800 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $252/Night
7 Nights - CA $1,763
House
10.0(216 Reviews)
2 Bedrooms
1 Bath
6 Guests
2064 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $239/Night
7 Nights - CA $1,675
House
10.0(214 Reviews)
2 Bedrooms
1 Bath
6 Guests
1901 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
CA $251/Night
7 Nights - CA $1,760
Cabin
10.0(201 Reviews)
2 Bedrooms
2 Baths
6 Guests
1100 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $278/Night
7 Nights - CA $1,946
Cottage
10.0(167 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $268/Night
7 Nights - CA $1,878
Cabin
10.0(164 Reviews)
2 Bedrooms
1 Bath
4 Guests
900 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $266/Night
7 Nights - CA $1,862
House
10.0(148 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
CA $179/Night
7 Nights - CA $1,255
Cabin
10.0(147 Reviews)
2 Bedrooms
1 Bath
4 Guests
900 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $266/Night
7 Nights - CA $1,862
House
10.0(137 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $400/Night
7 Nights - CA $2,799
House
10.0(134 Reviews)
1 Bedroom
1 Bath
2 Guests
900 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
CA $138/Night
7 Nights - CA $965
House
10.0(124 Reviews)
2 Bedrooms
1 Bath
4 Guests
700 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $319/Night
7 Nights - CA $2,235
