59+ Old Bennington Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Old Bennington

Discover more than 59 StayAndPlay accommodations in Old 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 Old Bennington, VT.

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 Old 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 Old Bennington pet-friendly golf accommodations and easily book your dream golf resort or villa rental in Old Bennington with StayAndPlay.

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Frequently Asked Questions About Old Bennington Holiday Rentals

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

There are many holiday rentals available in Old Bennington; however, here are a few of the most popular holiday homes listed in Old 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 Old Bennington to find one that works for you.
Yes, there are 59 self-catering family homes and holiday rentals in Old Bennington.
There are more than 59 luxury holiday homes in or near Old Bennington, according to 2025 data from StayAndPlay. Consider these homes for your next holiday:
Yes, there are 59 pet friendly rentals that are available in Old Bennington.