Welcome to Bennington Properties - Vacation Rentals in Sunriver & Caldera Springs

You’ve spent the entire year saving up for this special trip. Months searching for the right destination – the perfect mix of recreation and relaxation that will allow you to reconnect with friends, family and loved ones. Now, you have one chance to get it right when choosing your home-away-from-home for the long weekend or week. Welcome to Bennington Properties. There’s something different about a vacation planned through Bennington Properties. It’s personal and unique.

As a small, family owned and operated business, we understand the concept of ‘togethering’ with the ones you love. Here, you’re family. We take pride in helping you plan and book your trip as if it was our very own. No detail is too small and nothing goes overlooked. The anticipation of your vacation begins to take shape the moment we answer the phone, and it doesn’t stop there. Our staff takes the time to get to know you and your travel partners in order to find out what you want – and what you don’t want- from the trip, and then make recommendations on the perfect house or condo for your experience.

We’re available to attend to every detail of your trip, from assistance in activity planning, to dining recommendations and tee times. Every one of Bennington Properties’ nearly 160 individual properties - each one unique and distinct in its very own way- is carefully screened to ensure it meets our demanding criteria. From hot tubs and complimentary bicycles in all units, to free move rentals, popcorn, and high-speed internet, we understand the little individual details that collectively make a big difference.

And because your dog is part of your family, they are just as welcome here as you are. We even go as far as providing an off-leash play area and on-site dog wash at our management offices for your dog to exercise or clean up after a day of frolicking in the wilderness. Whether you’re booking a romantic escape for two, a family getaway for four, or a reunion for 16, Bennington Properties is there every step of the way to help you create a lifetime of memories from a single vacation. Ensuring that perfect “Remember the time we went to Sunriver?” moment for your family, your friends and yourself.

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