Hillside Winter Rental
House
10.0(21 Reviews)
2 Bedrooms
1 Bath
5 Guests
Hot Tub
Parking
Internet
Child Friendly
US $264/Night
7 Nights - US $1,850
House
10.0(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
2002.09 ft²
Fireplace/Heating- Parking
- Internet
- Child Friendly
US $244/Night
7 Nights - US $1,708
Hotel
8.8(665 Reviews)
1 Bath
- Fireplace/Heating
Breakfast
Kitchen- Parking
US $175/Night
7 Nights - US $1,228
Condo
9.6(4 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
Balcony/Terrace- Kitchen
- Parking
US $223/Night
7 Nights - US $1,558
Hotel
8.8(383 Reviews)
11 Baths
400.22 ft²
Private Pool- Fireplace/Heating
Pool- Balcony/Terrace
US $164/Night
7 Nights - US $1,150
House
9.8(20 Reviews)
4 Bedrooms
2 Baths
10 Guests
2000 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
US $505/Night
7 Nights - US $3,535
Hotel
8.3(134 Reviews)
8 Baths
456.12 ft²
Spa- Fireplace/Heating
- Balcony/Terrace
Pet Friendly
US $218/Night
7 Nights - US $1,527
House
9.4(13 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $432/Night
7 Nights - US $3,027
Hotel
7.5(98 Reviews)
1 Bath
290.63 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $112/Night
7 Nights - US $784
House
8.8(49 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $294/Night
7 Nights - US $2,057
House
8.4(5 Reviews)
3 Bedrooms
2 Baths
6 Guests
1650 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $479/Night
7 Nights - US $3,351
House
8.0(1 Review)
1 Bedroom
2 Baths
8 Guests
- Pet Friendly
- Kitchen
- Parking
Air Conditioner
US $428/Night
7 Nights - US $2,996
Why Choose Rent By Owner for your Hillside 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 Hillside
How to Book Your Hillside 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 Hillside
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 Hillside, IL
South shore hospital
Frequently Asked Questions About Hillside Winter Rentals
1. What are the top Winter Rentals in Hillside?
There are a lot of options in Hillside. If you plan on staying in the Hillside area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Winter Rentals in Hillside:
2. How many Winter Rentals are available in Hillside?
Currently, the total number of properties listed by RBO in 2026 is over 31 in the Hillside area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in Hillside.
More Rentals You May Like Near Hillside
House
8.0(1 Review)
3 Bedrooms
2 Baths
6 Guests
1700 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $374/Night
7 Nights - US $2,621
House
4 Bedrooms
3 Baths
9 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $558/Night
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Condo
10.0(3 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $212/Night
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New
House
1 Bedroom
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
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House
10.0(2 Reviews)
3 Bedrooms
2 Baths
10 Guests
1249 ft²
US $485/Night
7 Nights - US $3,393
House
9.8(8 Reviews)
3 Bedrooms
2 Baths
6 Guests
2000 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $229/Night
7 Nights - US $1,606
House
9.0(6 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $378/Night
7 Nights - US $2,646
House
8.0(2 Reviews)
4 Bedrooms
2 Baths
8 Guests
1300 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $454/Night
7 Nights - US $3,176
House
4 Bedrooms
3 Baths
10 Guests
2347 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $454/Night
7 Nights - US $3,176
House
10.0(1 Review)
4 Bedrooms
2 Baths
7 Guests
1227 ft²
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- Pet Friendly
US $552/Night
7 Nights - US $3,861
House
9.6(5 Reviews)
2 Bedrooms
1 Bath
5 Guests
1089 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $217/Night
7 Nights - US $1,519
House
5.0(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Air Conditioner
US $139/Night
7 Nights - US $973
