Upper South Side Cottage Rentals & Holiday Homes

Find the best cottages in Upper South Side - We found 473 exact matches

About Upper South Side Cottage Rentals on Treehouse Rentals

Looking for enchanting cottages near Upper South Side for your next getaway? Treehouse Rentals offers more than 473 unique treetop escapes and forest hideaways, perfect for your family or group trip. Discover treehouses nestled amidst nature, featuring amenities like private decks, kid-friendly designs, and proximity to local attractions. These rentals provide an exceptional experience, catering to families, friends, couples, or adventurous travelers.

Planning a treetop retreat or a nature-based getaway for your group? Treehouse Rentals provides a variety of accommodations, including luxury treehouses, off-grid cabins, and cozy forest homes, connecting you directly with property owners to secure the best rates.

Explore 473 treehouses and exceptional nature-based accommodations in Upper South Side with Treehouse Rentals. Find unique Airbnb-style and VRBO-style treehouses perfect for your weekend escape, summer vacation, or romantic retreat, all within your budget.

Show more
Show less

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 Treehouse Rentals

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 Treehouse Rentals shows that there are Over 473 private swimming pools or cottages with indoor pools in the Upper South Side area along with other great amenities.
About 473 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 Treehouse Rentals
Yes, there are luxury cottages in Upper South Side. Find more luxury, lakefront, winter, & last-minute cottage rentals near Upper South Side.