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43+ Chesterfield Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Chesterfield

Discover more than 43 treehouse rentals in Chesterfield, perfect for your holiday adventure. Treehouse offers treetop accommodations with everything you need for a relaxing escape near Chesterfield, IN.

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 Chesterfield? 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 Chesterfield pet-friendly treehouse rentals and easily book your dream treehouse vacation rental in Chesterfield with TreeHouse.

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Frequently Asked Questions About Chesterfield Holiday Rentals

There are a lot of options in Chesterfield. If you plan on staying in the Chesterfield 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 Chesterfield:

There are many holiday rentals available in Chesterfield; however, here are a few of the most popular holiday homes listed in Chesterfield 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 Chesterfield to find one that works for you.
Yes, there are 43 self-catering family homes and holiday rentals in Chesterfield.
There are more than 43 luxury holiday homes in or near Chesterfield, according to 2025 data from Treehouse Rentals. Consider these homes for your next holiday:
Yes, there are 43 pet friendly rentals that are available in Chesterfield.