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118+ Chilmark Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Chilmark

Discover more than 118 treehouse rentals in Chilmark, perfect for your holiday adventure. Treehouse offers treetop accommodations with everything you need for a relaxing escape near Chilmark, MA.

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

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Frequently Asked Questions About Chilmark Holiday Rentals

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

There are many holiday rentals available in Chilmark; however, here are a few of the most popular holiday homes listed in Chilmark 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 Chilmark to find one that works for you.
Yes, there are 118 self-catering family homes and holiday rentals in Chilmark.
There are more than 118 luxury holiday homes in or near Chilmark, according to 2025 data from Treehouse Rentals. Consider these homes for your next holiday:
Yes, there are 118 pet friendly rentals that are available in Chilmark.