104+ Middlebury Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Middlebury

Discover more than 104 holiday rentals in Middlebury. Casai holiday homes have everything you need to find a place to stay near Middlebury, CT.

Whether you are looking for luxury villas in Middlebury, furnished homes, unique style condos, flats, cozy cottages for a romantic getaway, spacious apartments for family holidays, or stylish accommodations for a business trip, we can help you find the perfect place. Our holiday rentals include top amenities such as indoor/outdoor swimming pools, kitchen facilities, gyms, hot tubs, Internet connectivity, and more.

If you are planning to travel to Middlebury with a whole family or group, Casai holiday accommodations will make your trip memorable. We have plenty of places to stay in Middlebury for families, large parties, or private owner accommodations for long or short trips. Middlebury Pet-friendly holiday rentals are available. Book your favorite vacation rentals in Middlebury with Casai. Casai makes it easy to compare and book holiday rentals today.

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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 Casai.com 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 Casai.com. Consider these homes for your next holiday:
Yes, there are 104 pet friendly rentals that are available in Middlebury.