I have rented over a dozen homes in Annapolis over the last 3 years and The Bennett House is definitely in the top 5.
We rented the entire home. We are USNA parents (3 couples) who were in town visiting our mids and attending the Navy/AF Football game.
I will review each floor separately.
The bottom floor was my favorite as far as the kitchen and living space. It's just roomier than upstairs. We hosted a dinner for our boys and another mid and his parents one night. We made food ahead of time, so didn't cook in the home, only reheated in the oven. The island is very large and plenty of seating. Everyone ends up in the kitchen, so having this space was really nice. The living room is open to the kitchen and is quite large. Spilling out from there is the deep front porch with the most comfortable porch swing. The space is just set up perfect for entertaining. However, there is just one bedroom here. Our friends said the bed was super comfy. And the bathroom is a rustic modern design.
The kitchen was so well equipped. Seriously everything you need is there. Top quality from the silverware to the coffee mugs. The Nespresso maker was awesome to have.
The upstairs apartment is a great space. It has one king, one double and a pull out queen in the living room. Don't let "pull out" scare you. My son slept on it two nights and said it was as or more comfy than any bed he has slept in. All the beds had top quality bedding. The bathroom has plenty of fluffy towels.
I adored this kitchen, and you could totally prepare a meal. It just doesn't have the space that the downstairs has. Most folks who visit Annapolis end up at the restaurants; but this kitchen also had everything one needs to prepare a meal.
Evidently the outdoor space in the back will be undergoing a facelift. As for now, there is a very nice table for six, umbrella, grill and a fire pit with a few chairs around it. We did sit outside one night and it was lovely. I'm sure the updates will be fabulous.
The spaces were incredibly clean. Nothing found to be out of order, stained, etc.
I would highly recommend staying here. The whole house, or either upstairs or down. It's a perfect place for a group. Right around the corner from all the fun on West Street and about a 15 minute walk to the Academy.
Downside is parking. No off-street, so need to park in the deck. It's close. No in/out privilege and ran us $17 for each 24 hours.