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 PickleTrip

Searching for cottages to rent near Upper South Side? PickleTrip™ features more than 476 cottages that are perfect for your next pickleball getaway. Plan your ultimate holiday and discover luxury cottage rentals that are a few miles away from the lake or beach and have access to private courts or nearby facilities. These cottage rentals in Upper South Side 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. PickleTrip™’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Upper South Side.

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

PickleTrip™ boasts of 476 holiday cottages and places to stay in Upper South Side. The site provides unique Airbnb, VRBO, pickleball-ready 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.

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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 PickleTrip

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 PickleTrip 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 PickleTrip
Yes, there are luxury cottages in Upper South Side. Find more luxury, lakefront, winter, & last-minute cottage rentals near Upper South Side.