Winston Cottage Rentals & Holiday Homes

Find the best cottages in Winston - We found 91 exact matches

About Winston Cottage Rentals on SunSkiResorts

Searching for cottages to rent near Winston? SunSki features more than 91 cottages that are perfect for your next trip. Escape the snow and slopes and discover luxury cottage rentals just a few miles away from the lake or beach. These cottage rentals in Winston offer hot baths, are kid-friendly & family-friendly, and are situated near top local attraction spots, ensuring guests have the best travel experience possible. SunSki’s cottage listings come in all shapes and sizes, catering to large groups, friends, or couples in Winston.

Planning to travel to the lakeside, beach, or mountain area? SunSki’s cottage rentals offer a wide selection, providing direct access to the owners of these cottage rentals and offering you the best opportunity to find a good price.

SunSki boasts of 91 holiday cottages and places to stay in Winston. The site provides unique Airbnb, VRBO, ski-style cottages to fit your trip or getaway with your friends and family. Whether it's a weekend getaway, spring break, summer vacation, or annual holiday, all fit within your budget.

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Frequently Asked Questions About Winston Rental Cottages

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

The average cost for a cottage rental in Winston is $268 per night. SunSki has a wide list of great cottages near Winston that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage rentals in Winston that allow you to bring your pet:

See all pet-friendly vacation rentals in Winston on SunSkiResorts

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Winston to find one that works for you.
As of 2025, the data from SunSkiResorts shows that there are Over 91 private swimming pools or cottages with indoor pools in the Winston area along with other great amenities.
About 91 cottages in Winston boast of premium hot tubs. Some of the popular places to stay with hot tubs include:See all holiday vacation rentals in Winston on SunSkiResorts
Yes, there are luxury cottages in Winston. Find more luxury, lakefront, winter, & last-minute cottage rentals near Winston.