Island Lake Winter Rentals & Holiday Homes

Discover winter rentals Island Lake - We found 40 exact matches

About Island Lake Winter Rental on PickleTrip

Planning on a winter vacation in Island Lake? Discover 40 places to stay in Island Lake, for those traveling with their family, friends, in groups, or for a wedding retreat.

At PickleTrip™, we have a wide range of listings for accommodations in Island Lake, IL that are perfect for your winter trip or seasonal escape. Our listings have private vacation homes, cabins, condos, villas, resorts, or pet-friendly apartments that you would love. PickleTrip™ winter vacation homes have top amenities, including Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.

Island Lake winter accommodation starts at US $255, and the most popular properties in Island Lake are cabins, bungalows, and rental homes by owner. Planning snowboarding on your next winter vacation? We have many snowboard-friendly ski resorts, chalets, and cabins that are available for you to rent. These rentals are available for both short-term stays and long-term stays, whether you are traveling for a weekend, monthly, or a longer stay, PickleTrip will make your winter trip memorable.

PickleTrip™ offers a great deal for travelers planning on renting a place in Island Lake, to enjoy these benefits and to book your winter vacation homes, go to PickleTrip™ filter option, enter your travel date, check the filters to narrow down your property type and amenities, then choose from a long list of our winter vacation rentals without hassle. Our interactive map is also available, to view all places to stay in or around Island Lake and unlock even more amazing deals.

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Frequently Asked Questions About Island Lake Winter Rentals

There are a lot of options in Island Lake. If you plan on staying in the Island Lake area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Island Lake:

The average cost for winter rentals in Island Lake is $255 per night. PickleTrip has a wide list of great winter places to stay near Island Lake that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage/chalet rentals in Island Lake that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Island Lake on PickleTrip

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Island Lake to find what works for you.
As of 2025, the data from PickleTrip shows that there are over 40 private swimming pools or indoor pools accommodations near Island Lake along with other great amenities.

About 40 holiday rentals in Island Lake boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:

Yes, there are many luxury places to stay in Island Lake for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Island Lake with all the best amenities for your next trip.