You have this huge river next to a small town at the base of a hill in which you can gaze at old architecture, tour historic landmarks, and eat at non-chain restaurants. There is this hotel on the side of the hill that looks down at the whole town while you are doing all of this. It is kind of like the "Hollywood" sign as you can spot it from almost every point in the town. The appearance, alone, makes you want to say, "hey, I want to stay there." So, my wife and I took part of a weekend trip and stayed at a room in the Hillside Inn.
The owners of the hotel could take an approach like, "We don't need to put much care into the facility as it is the most obvious place to stay in town. We can just charge outrageous prices to tourists and claim that you are paying for the view and history instead of getting a comfortable stay." But they don't. The room we had felt like one of the cleanest, updated places we have ever stayed at. The bed was comfortable, the bathroom was clean, the TV was clear, the air-conditioning worked, and the balcony was large. The breakfast was served in the large banquet room and had a continental breakfast as well as a waffle iron, bacon, and sausage. If you really want to pick apart the hotel and find something bad with it you can say that you occasionally hear the plumbing run from other rooms when you are in the bathroom. You may lose water pressure and temperature slightly while taking a shower, but these things were minor. We had no major problems staying in the room and it was quite comfortable.
The main reason to stay here and the unique factor comes in the private balcony. It is just cool to go on it and look out at the town, river, and bridge. That is the reason we stayed at this place. From the pictures on the wall it looks like the place was built in the 20's, but it had been extensively renovated to be unrecognizable to the original structure sometime in the 60's or 70's. As the years have rolled on the trees have gotten taller and I'm betting the views of the river are not as spectacular as they might have been in the past. From our first floor view we actually could not see the river except for at the bridge. Even the view downtown was blocked by a tree that stood alone in the front yard of the inn. But, the view we did have of the bridge, hills, and rest of the town was nice enough to not have me wander down to the front desk demanding another room (but I would suggest to others while booking the rooms to ask for higher floors).
I would definitely suggest people visit this hotel if they are staying in Madison, IN. And while they do not have some the amenities that other hotels provide like pools, restaurants, or gyms, the uniqueness and cleanliness of the hotel will leave you happy with your stay.
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.