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37+ Bennington Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Bennington

Discover more than 37 StayAndPlay accommodations in Bennington, perfect for your golf getaway. StayAndPlay offers luxury golf resorts, private villas, and vacation rentals with everything you need for a relaxing escape near Bennington, IN.

Whether you're seeking upscale golf-front resorts, private luxury villas, spacious vacation homes, or family-friendly golf retreats, we can help you find the ideal stay. Our rentals feature top-tier amenities such as private pools, fully equipped kitchens, outdoor patios, hot tubs, and Wi-Fi, ensuring your group enjoys a comfortable and memorable stay.

Planning a group golf trip to Bennington? StayAndPlay guarantees a unique and unforgettable experience with plenty of options for families, large groups, or private rentals for long or short stays. Explore our Bennington pet-friendly golf accommodations and easily book your dream golf resort or villa rental in Bennington with StayAndPlay.

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Frequently Asked Questions About Bennington Holiday Rentals

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

There are many holiday rentals available in Bennington; however, here are a few of the most popular holiday homes listed in Bennington on our website:
At StayAndPlay most of our places to stay are perfect for families. Check out the complete list of holiday homes in Bennington to find one that works for you.
Yes, there are 37 self-catering family homes and holiday rentals in Bennington.
There are more than 37 luxury holiday homes in or near Bennington, according to 2025 data from StayAndPlay. Consider these homes for your next holiday:
Yes, there are 37 pet friendly rentals that are available in Bennington.