Apartment
10.0(419 Reviews)
1 Bedroom
4 Guests
Parking
Pool
Ocean View
View
US $219/Night
7 Nights - US $1,532
Illinois Winter Rentals & Holiday Homes
Discover winter rentals Illinois - We found 7225 exact matches
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Compare Winter Rental in Illinois
10.0
Bed & Breakfast
10.0(24 Reviews)
4 Bedrooms
8 Guests
- Parking
Balcony/Terrace
Air Conditioner
Internet
US $247/Night
7 Nights - US $1,729
Bed & Breakfast
10.0(566 Reviews)
1 Bedroom
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $195/Night
7 Nights - US $1,364
Apartment
10.0(234 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $242/Night
7 Nights - US $1,695
US $208/Night
7 Nights - US $1,456
Condo
10.0(231 Reviews)
2 Bedrooms
9 Guests
Hot Tub- Parking
- Balcony/Terrace
Kitchen
US $458/Night
7 Nights - US $3,209
House
10.0(12 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $159/Night
7 Nights - US $1,113
Apartment
10.0(219 Reviews)
2 Bedrooms
8 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $455/Night
7 Nights - US $3,187
House
10.0(11 Reviews)
2 Bedrooms
4 Guests
Private Pool- Pool
- Air Conditioner
- Internet
US $133/Night
7 Nights - US $931
Condo
10.0(219 Reviews)
1 Bedroom
5 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $296/Night
7 Nights - US $2,073
Bed & Breakfast
10.0(9 Reviews)
5 Bedrooms
12 Guests
Breakfast- Parking
- Balcony/Terrace
- View
US $235/Night
7 Nights - US $1,645
House
10.0(108 Reviews)
1 Bedroom
2 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $168/Night
7 Nights - US $1,176
House
10.0(6 Reviews)
4 Bedrooms
12 Guests
- Parking
- View
- Air Conditioner
- Internet
US $358/Night
7 Nights - US $2,504
Apartment
10.0(103 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $349/Night
7 Nights - US $2,441
Apartment
10.0(92 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $151/Night
7 Nights - US $1,057
Apartment
10.0(89 Reviews)
1 Bedroom
3 Guests
- Hot Tub
- Parking
Spa- Balcony/Terrace
US $249/Night
7 Nights - US $1,743
House
10.0(85 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $277/Night
7 Nights - US $1,941
House
10.0(75 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $295/Night
7 Nights - US $2,062
House
10.0(74 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $321/Night
7 Nights - US $2,248
Condo
10.0(68 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $274/Night
7 Nights - US $1,916
Apartment
10.0(64 Reviews)
1 Bedroom
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $308/Night
7 Nights - US $2,155
Condo
10.0(63 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $526/Night
7 Nights - US $3,685
Apartment
10.0(62 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $492/Night
7 Nights - US $3,442
Apartment
10.0(58 Reviews)
2 Bedrooms
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $487/Night
7 Nights - US $3,407
About Illinois Winter Rental on BedroomVillas
At BedroomVillas, we feature a wide range of listings for accommodations in Illinois, IL that are perfect for your winter trip or seasonal escape. Our listings include hotels, private vacation homes, cabins, condos, villas, resorts, or pet-friendly apartments that travelers are sure to love. BedroomVillas winter vacation homes have top amenities, including Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.
Whether you are escaping the snow or running to it, BedroomVillas helps connect you to the best cabins, bungalows, lodges, and villas, as well as the best places to stay in both sun and ski resorts. BedroomVillas will make your winter getaway an unforgettable experience.
BedroomVillas offers luxury finds for travelers planning on renting a place in Illinois, to enjoy these benefits and to book your winter vacation homes, go to the BedroomVillas filter option, enter your travel date, check the filters to narrow down your property type and amenities, then choose from a long list of incredible winter vacation rentals without hassle. Our interactive map is also available, so you can view destinations spanning the globe or around Illinois and unlock even more amazing deals. Relax with BedroomVillas.
Winter Rental: Explore Top Destinations
Frequently Asked Questions About Illinois Winter Rentals
What are the top rated 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!
- Escape! Hot Tub, Fire Pit, 3 Decks, WiFi, Pool Table
- 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
- Picture Perfect Galena Getaway on Golf Course | 4 Bed 4 Bath | Hot Tub & FirePit
- 55th-Floor 3BR Duplex Penthouse Lake & City Views
- The Cottage on Lake Galena
How much does it cost to rent a place to stay near Illinois in the wintertime?
The average cost for winter rentals in Illinois is $389 per night. BedroomVillas has a wide list of great winter places to stay near Illinois that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Illinois that allow pets?
Yes, here are the top cottage/chalet rentals in Illinois that allow you to bring your pet or dog:
- 52nd Floor MagMile Penthouse Views Fireplace Pool
- Lamberson Guest House
- The Sono Chicago
- 51st Floor MagMile Penthouse Views Balcony Pool
See all pet-friendly vacation rentals in Illinois on BedroomVillas
Do you have any winter rentals in Illinois that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Illinois to find what works for you.
Are there winter accommodations in Illinois that have indoor swimming pools?
As of 2026, the data from BedroomVillas shows that there are over 7225 private swimming pools or indoor pools accommodations near Illinois along with other great amenities.
Do any winter holiday rentals in Illinois have hot tubs?
About 7225 holiday rentals in Illinois boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Illinois?
Yes, there are many luxury places to stay in Illinois for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Illinois with all the best amenities for your next trip.
