47+ Chester Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Chester

Discover more than 47 treehouse rentals in Chester, perfect for your holiday adventure. Treehouse offers treetop accommodations with everything you need for a relaxing escape near Chester, MA.

Whether you're seeking luxury multi-level treehouses, rustic forest cabins, cozy off-grid retreats, or family-friendly treehouse lodgings, we can help you find the ideal place. Our rentals feature top-notch amenities such as private decks, fully equipped kitchens, fire pits, hot tubs, and Wi-Fi, ensuring your group enjoys a comfortable and memorable stay.

Planning a group getaway to Chester? TreeHouse guarantees a unique and unforgettable experience with plenty of options for families, large groups, or private rentals for long or short stays. Explore our Chester pet-friendly treehouse rentals and easily book your dream treehouse vacation rental in Chester with TreeHouse.

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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 Treehouse Rentals 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 Treehouse Rentals. Consider these homes for your next holiday:
Yes, there are 47 pet friendly rentals that are available in Chester.