Chicago Cottage Rentals & Holiday Homes

Searching for cottages to rent near Chicago? Top Winter Vacations features more than 5 cottages that are perfect for your next trip. Discover luxury cottage rentals that are a few miles away from the lake or beach. These cottage rentals in Chicago have hot baths, are kid-friendly & family-friendly, and are near top local attraction spots, to give guests the best travel experience they could ever wish for. Top Winter Vacations’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Chicago.

Are you planning to travel to the lakeside, beach, or mountain area? Top Winter Vacations’s cottage rentals offers a wide selection, giving you direct access to the owners of these cottage rentals, and offering you the best opportunity to find a good price.

Top Winter Vacations boasts of 5 holiday cottages and places to stay in Chicago. The site provides unique Airbnb, VRBO, Top Winter Vacations-style cottages to fit your trip or get away with your friends and family. This can be a weekend getaway, spring break, summer vacation, or annual holiday -- all fitting within your budget.