1. USA
  2. Oregon
  3. Roseburg
  4. Winston
  5. Cottage Rentals

Winston Cottage Rentals & Holiday Homes

Find the best cottages in Winston - We found 5 exact matches

About Winston Cottage Rentals on Casai.com

Searching for cottages to rent near Winston? Casai 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 Winston 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. Casai’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Winston.

Are you planning to travel to the lakeside, beach, or mountain area? Casai’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.

Casai boasts of 5 holiday cottages and places to stay in Winston. The site provides unique Airbnb, VRBO, Casai-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.

Show more
Show less

Frequently Asked Questions About Winston Rental Cottages

The average cost for a cottage rental in Winston is $137 per night. Casai 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 Casai.com

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 2026, the data from Casai.com shows that there are Over 5 private swimming pools or cottages with indoor pools in the Winston area along with other great amenities.
About 5 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 Casai.com
Yes, there are luxury cottages in Winston. Find more luxury, lakefront, winter, & last-minute cottage rentals near Winston.