Upper South Side Cottage Rentals & Holiday Homes

Find the best cottages in Upper South Side - We found 476 exact matches

About Upper South Side Cottage Rentals on SunSkiResorts

Searching for cottages to rent near Upper South Side? SunSki features more than 476 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 Upper South Side 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 Upper South Side.

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 476 holiday cottages and places to stay in Upper South Side. 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 Upper South Side Rental Cottages

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

Yes, here are the top cottage rentals in Upper South Side that allow you to bring your pet:

See all pet-friendly vacation rentals in Upper South Side on SunSkiResorts

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Upper South Side to find one that works for you.
As of 2025, the data from SunSkiResorts shows that there are Over 476 private swimming pools or cottages with indoor pools in the Upper South Side area along with other great amenities.
About 476 cottages in Upper South Side boast of premium hot tubs. Some of the popular places to stay with hot tubs include:See all holiday vacation rentals in Upper South Side on SunSkiResorts
Yes, there are luxury cottages in Upper South Side. Find more luxury, lakefront, winter, & last-minute cottage rentals near Upper South Side.