104+ Middlebury Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Middlebury

Discover more than 104 treehouse rentals in Middlebury, perfect for your holiday adventure. Treehouse offers treetop accommodations with everything you need for a relaxing escape near Middlebury, 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 Middlebury? 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 Middlebury pet-friendly treehouse rentals and easily book your dream treehouse vacation rental in Middlebury with TreeHouse.

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Frequently Asked Questions About Middlebury Holiday Rentals

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

There are many holiday rentals available in Middlebury; however, here are a few of the most popular holiday homes listed in Middlebury 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 Middlebury to find one that works for you.
Yes, there are 104 self-catering family homes and holiday rentals in Middlebury.
There are more than 104 luxury holiday homes in or near Middlebury, according to 2025 data from Treehouse Rentals. Consider these homes for your next holiday:
Yes, there are 104 pet friendly rentals that are available in Middlebury.