47+ Chester Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Chester

Discover more than 47 holiday rentals in Chester. Casai holiday homes have everything you need to find a place to stay near Chester, MA.

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

Show more
Show less

Frequently Asked Questions About Chester Holiday Rentals

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

There are many holiday rentals available in Chester; however, here are a few of the most popular holiday homes listed in Chester 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 Chester to find one that works for you.
Yes, there are 47 self-catering family homes and holiday rentals in Chester.
There are more than 47 luxury holiday homes in or near Chester, according to 2025 data from Casai.co.za. Consider these homes for your next holiday:
Yes, there are 47 pet friendly rentals that are available in Chester.