53+ Chesterville Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Chesterville

Discover more than 53 holiday rentals in Chesterville. Rent By Owner holiday homes has everything you need to find a place to stay near Chesterville, ON.

Whether you are looking for luxury villas in Chesterville, furnished homes, unique style condos, flats, cozy cottages for a romantic getaway, spacious apartment for family holidays, or stylish accommodation 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 Chesterville with a whole family or group, RBO holiday accommodations make your trip memorable. We have plenty of places to stay in Chesterville for families, large parties, or private owner accommodations for long or short trips. Chesterville Pet-friendly holiday rentals are available. Book your favorite vacation rentals in Chesterville with Rent By Owner. RBO makes it easy to compare and book holiday rentals today.

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Frequently Asked Questions About Chesterville Holiday Rentals

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

There are many holiday rentals available in Chesterville; however, here are a few of the most popular holiday homes listed in Chesterville on our website:
At Rent By Owner most of our places to stay are perfect for families. Check out the complete list of holiday homes in Chesterville to find one that works for you.
Yes, there are 53 self-catering family homes and holiday rentals in Chesterville.
There are more than 53 luxury holiday homes in or near Chesterville, according to 2025 data from Rent By Owner. Consider these homes for your next holiday: