89+ Windham County Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Windham County

Discover more than 89 treehouse rentals in Windham County, perfect for your holiday adventure. Treehouse offers treetop accommodations with everything you need for a relaxing escape near Windham County, CT.

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

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Frequently Asked Questions About Windham County Holiday Rentals

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

There are many holiday rentals available in Windham County; however, here are a few of the most popular holiday homes listed in Windham County 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 Windham County to find one that works for you.
Yes, there are 89 self-catering family homes and holiday rentals in Windham County.
There are more than 89 luxury holiday homes in or near Windham County, according to 2025 data from Treehouse Rentals. Consider these homes for your next holiday:
Yes, there are 89 pet friendly rentals that are available in Windham County.