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117+ Chilmark Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Chilmark

Discover more than 117 holiday rentals in Chilmark. Casai holiday homes have everything you need to find a place to stay near Chilmark, MA.

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

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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 Casai.ca 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 117 self-catering family homes and holiday rentals in Chilmark.
There are more than 117 luxury holiday homes in or near Chilmark, according to 2025 data from Casai.ca. Consider these homes for your next holiday:
Yes, there are 117 pet friendly rentals that are available in Chilmark.