We stayed at the studio: full kitchen, nice bed, super cozy arm chair, great bathroom, close to the hot tub. We had delicious organic breakfasts (not the usual sausages and bacon). The owner, Annie, was very kind and went out of the way to make our stay comfortable. We hightly recommend this place and will come again! more

The innkeeper, Annie, is more like an old friend than an innkeeper. Her warmth and generosity, combined with the comfortable, pampering decor of the rooms, make the Hillside Inn a true gem. If you're looking for a true home-away-from-home, you'll find that and much more here. In my opinion, this has to be the best bed and breakfast in Bend! more

This is the place to be if you want a warm, comforting atmosphere with a personal touch and presidential amenities! Annie is your host and she is much more than that! If you are here to relax she will ask what kind of wine or sparkling cider you would like in your room when you arrive, and whether you like... more

We stayed at the Hillside B & B for one night in August. (that was the dissapointment as we should have reserved a longer stay) Annie was very helpful in providing information on things we should do whilst in town and places to eat (If you like steak you MUST go to Gregs). Our room was fantastic, a very comfortable... more

We booked 3 nights at the Hillside Inn, greatly influenced by Tripadvisor reviews, and the positive reviews were right on target! Lovely and quiet neighborhood, comfy room, sparkling clean hot tub, great bathroom amenities, plus Annie. Unlike most B&Bs, where it's "this is what we're serving for breakfast," at the Hillside Inn, Annie asks "what would you like for breakfast... more

Annie is a charming, knowledgable hostess and great cook who has thought of everything you could want. Absolutely the most comfortable bed we have ever slept in - we wanted to take it with us! We stayed in the Studio suite and didn't want to leave. The location is perfect, just a 5 minute walk from the river and Drake... more

My respite at the Hillside Inn in Bend Oregon was completely by accident due to the majority of the typical business accomodations in the area being sold out as a result of a local PGA tournament. So I went looking for alternatives and lucked upon the Hillside who had just happened to have a last minute cancellation to squeeze in... more

My daughter and I spent one night at the Hillside Inn. What a lovely place! Annie has thought of everything possible. Fresh fruit and drinks were waiting for us upon arrival. Detailed information about where to go and places to eat. Breakfast was fantastic! My teenage daughter is vegan and she went out of her way to accommodate her needs.... more

It was our second time to spend time with Annie, that's right....it's like visiting a great friend. The room we stayed in was the studio and it was truly outstanding. Spending the later part of the afternoons on the outside porch listening to the fountain and watching the birds and fish at play was so relaxing. Annie has made this... more