114+ Chester Shores Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Chester Shores

Discover more than 114 treehouse rentals in Chester Shores, perfect for your holiday adventure. Treehouse offers treetop accommodations with everything you need for a relaxing escape near Chester Shores, NY.

Whether you're seeking luxury multi-level treehouses, rustic forest cabins, cozy off-grid retreats, or family-friendly treehouse lodgings, we can help you find the ideal place. Our rentals feature top-notch amenities such as private decks, fully equipped kitchens, fire pits, hot tubs, and Wi-Fi, ensuring your group enjoys a comfortable and memorable stay.

Planning a group getaway to Chester Shores? TreeHouse guarantees a unique and unforgettable experience with plenty of options for families, large groups, or private rentals for long or short stays. Explore our Chester Shores pet-friendly treehouse rentals and easily book your dream treehouse vacation rental in Chester Shores with TreeHouse.

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Frequently Asked Questions About Chester Shores Holiday Rentals

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

There are many holiday rentals available in Chester Shores; however, here are a few of the most popular holiday homes listed in Chester Shores on our website:
At Treehouse Rentals most of our places to stay are perfect for families. Check out the complete list of holiday homes in Chester Shores to find one that works for you.
Yes, there are 114 self-catering family homes and holiday rentals in Chester Shores.
There are more than 114 luxury holiday homes in or near Chester Shores, according to 2025 data from Treehouse Rentals. Consider these homes for your next holiday:
Yes, there are 114 pet friendly rentals that are available in Chester Shores.