Discover winter rentals Kenwood - We found 136 exact matches
About Kenwood Winter Rental on Vacation Cottage
At Vacation Cottage, we showcase a diverse array of accommodations in Kenwood, IL perfect for your winter retreat or seasonal escape. Our listings encompass hotels, private vacation homes, cabins, condos, villas, resorts, and pet-friendly apartments, ensuring travelers find their ideal accommodation. Vacation Cottage's winter vacation homes boast premier amenities such as Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.
Whether you're seeking to escape the snow or embrace it, Vacation Cottage facilitates your connection to the finest cabins, bungalows, lodges, rent-by-owner homes, and the best accommodations in both sunny retreats and ski resorts. Vacation Cottage ensures your winter getaway becomes an unforgettable experience.
Vacation Cottage presents luxury options for travelers seeking to rent a place in Kenwood. To access these benefits and book your winter vacation home, simply utilize the Vacation Cottage filter option. Enter your travel dates, refine your search with filters for property type and amenities, then choose from our extensive list of exceptional winter vacation rentals hassle-free. Our interactive map further enhances your experience, allowing you to explore destinations worldwide or within Kenwood and unlock incredible deals. Life is Better at the Cottage with Vacation Cottage.
Frequently Asked Questions About Kenwood Winter Rentals
What are the top rated Winter Rentals in Kenwood?
There are a lot of options in Kenwood. If you plan on staying in the Kenwood area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Kenwood:
- 1 mile walk to 43rd St .beach. In Historic North Kenwood. 6.3 miles to Navy Pier
- Penthouse, Lux stay near Downtown, McComick & Lake
- Gorgeous historic mansion on UChicago campus. Renovation with original detail.
- Large historic home minutes from downtown Chicago and the lakefront.
- Gather, relax, enjoy— in chic luxury home near Lake Michigan & McCormick Center
- The Woodlawn Oasis is an absolutely beautiful newly rehabbed apartment!
- Beautiful Bronzeville Duplex!
- The Hyde Park Haven
- Modern 4 Bed, 3.5 Bath Home | Near Sox & McCormick
- Spacious unit in historic gem
How much does it cost to rent a place to stay near Kenwood in the wintertime?
The average cost for winter rentals in Kenwood is $362 per night. Vacation Cottage has a wide list of great winter places to stay near Kenwood that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Kenwood that allow pets?
Yes, here are the top cottage/chalet rentals in Kenwood that allow you to bring your pet or dog:
- Penthouse, Lux stay near Downtown, McComick & Lake
- Parisian Retreat 6min to Main Quandrangle U of C
- Dubois Guest House Room 202
- Spacious unit in historic gem
See all pet-friendly vacation rentals in Kenwood on Vacation Cottage
Do you have any winter rentals in Kenwood that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Kenwood to find what works for you.
Are there winter accommodations in Kenwood that have indoor swimming pools?
As of 2025, the data from Vacation Cottage shows that there are over 136 private swimming pools or indoor pools accommodations near Kenwood along with other great amenities.
Do any winter holiday rentals in Kenwood have hot tubs?
About 136 holiday rentals in Kenwood boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Kenwood?
Yes, there are many luxury places to stay in Kenwood for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Kenwood with all the best amenities for your next trip.
