644+ Chestnut Hill Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Chestnut Hill

Discover more than 644 holiday rentals in Chestnut Hill. Casai holiday homes have everything you need to find a place to stay near Chestnut Hill, MA.

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

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Frequently Asked Questions About Chestnut Hill Holiday Rentals

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

There are many holiday rentals available in Chestnut Hill; however, here are a few of the most popular holiday homes listed in Chestnut Hill on our website:
At Casai.co.za most of our places to stay are perfect for families. Check out the complete list of holiday homes in Chestnut Hill to find one that works for you.
Yes, there are 644 self-catering family homes and holiday rentals in Chestnut Hill.
There are more than 644 luxury holiday homes in or near Chestnut Hill, according to 2025 data from Casai.co.za. Consider these homes for your next holiday:
Yes, there are 644 pet friendly rentals that are available in Chestnut Hill.