Near North Side Winter Rentals & Holiday Homes

Discover winter rentals Near North Side - We found 213 exact matches

About Near North Side Winter Rental on BedroomVillas

At BedroomVillas, we feature a wide range of listings for accommodations in Near North Side, 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 rent-by-owner homes, 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 Near North Side, 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 Near North Side and unlock even more amazing deals. Relax with BedroomVillas.

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Frequently Asked Questions About Near North Side Winter Rentals

The average cost for winter rentals in Near North Side is $701 per night. BedroomVillas has a wide list of great winter places to stay near Near North Side 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 Near North Side that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Near North Side on BedroomVillas

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Near North Side to find what works for you.
As of 2025, the data from BedroomVillas shows that there are over 213 private swimming pools or indoor pools accommodations near Near North Side along with other great amenities.

About 213 holiday rentals in Near North Side 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 Near North Side for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Near North Side with all the best amenities for your next trip.