We had stayed here twice before, about 12 years ago and then about 5 years ago. Both prior visits had been wonderful, so we were very excited about the chance to visit Prospect Hill again. However, our memories did not match what we found...
When we checked in at 6 pm, the innkeeper told us that he no longer offered dinner on weeknights as it was 'just so much work' and instead gave us suggestions for restaurants in Charlottesville, over 25 miles away. We were stunned - the website implies that dinner is available and the last thing we wanted to do was drive a rental car to an unfamiliar city to search for a place to eat.
We had booked the Boy's Cabin, having stayed there on our last visit. We knew it was small and intimate, so that was fine, but we were not prepared for the worn appearence. The room looked old and tired, with dull furnishings. The bed was unspeakable... there was a dip in the mattress that kept us squashed together uncomfortably all night. When we went to breakfast in the morning, the shabby and neglected appearence of the grounds was immediately apparent. Flower beds were bare or overgrown, planters sat empty or weed-filled and ivy was climbing over everything. Breakfast was tasty, but the dining room was again worn and tired. We asked for a new room because of the issue with the bed, and were offered the cabin next door. The bed was better, but this room was equally neglected. The bedskirt was soiled, the curtain rods were too short and fell down when touched, one chair by the fire was broken, with a metal bar secured inadequately over the break. There was a sad and depressing feeling of decay.
For the prices charged ($295 plus tax), the accommodations were simply inadequate. To top it off, when we checked out the next day, the manager told us that she had looked at the bed in the Boy's Cabin, and agreed that it was 'not good enough'. However, as it was 'too late in the season to justify buying a new mattress and box springs', she had placed a sheet of plywood between the two and it was now much better. We were stunned!
No doubt, you will read other reviews, both positive and negative. But it is hard to imagine that any traveller paying $300-400 a night will be satisfied with this property. Perhaps someday the money and passion will be available to restore this property properly.

What a wonderful surprise. We picked it from reading reviews from several sites and looking at it online. We arrived 30 minuets before the wine tasting and took a stroll around the grounds. (Go on a cooler day as we did. It would probably be pretty hot in the summer). The ambience at the main house dining area was very cozy and intimate and the dinner time was lead off with a prayer for the food, the travelers and those at war. What a fine gentleman Mr. Sheehan is. A very generous wine tasting at the start had us feeling pretty good by dinner time. Very timely and hot dishes served on the price fixe. All local products makes you really appreciate the variety that Virginia country has to offer for dining. Excellent desert and all just the right size portions that left you satisfied.

My husband's parents and aunt/uncle have come to Prospect Hill many times over the years, and highly recommended it for us when we wanted a get-away.

As I read over the trip advisor reviews, I saw a similar pattern emerge: some travelers had an amazing trip and others felt the way we did, disappointed. I'm not sure how this happens at the same place, but I'm sure the rooms, food, etc. all make for a different experience. Ours was not good.

We were doing very well until dinner. We arrived mid-afternoon, fell in love immediately with our room (The Boys Cabin), sat around reading and relaxing for hours next to the lovely fire in our room and eating the yummy snacks. We then dressed up and walked over to the main house for dinner. The wine was average before dinner, but that's to be expected since they want you to purchase wine with dinner.

OH, the dinner. It was just really not good. I know they change the menu frequently, but this menu did not match any of the ones they listed in our room. The main issue was that the food was not only not gourmet, it was just bad. The broccoli soup tasted like Campbells, with some extra salt and pepper dumped in. The main course was pork tenderloin, and I don't eat pork generally...but I gave it a try- the flavors were just blah, boring and...oh yeah, the soup! I had to run to the restroom mid-way through dinner to "get rid" of the soup course. Perhaps it just didn't agree with me, but nothing tasted good, the desert was ho-hum, and I felt terrible after eating (AND PAYING) for this meal. I can't even remember the salad, I think it was ok.
The service at dinner: The hostess came around multiple times to ask how people were enjoying dinner, and after my husband said we thought the soup was rather salty, she specifically avoided even coming near our table the rest of the night! I don't appreciate that when you answer their question truthfully, you then get poor service. Don't ask if you really don't care. I guess that's how I felt about the meals and service at Prospect Hill- they didn't care who liked it or not.

Also, breakfast was ok. They advertise breakfast in bed, by the way, but the woman who checked us in said that she was unwilling to bring the tray and didn't have her usual guy to do it, because it was too cold. Again, this wasn't a big deal until after the bad dinner and bad service we got at the dinner. Plus it ruined the whole relaxation part.

I LOVED the boys cabin, but will likely never return because I don't want to have to leave to go somewhere else for dinner, and we certainly won't pay to eat their meals again. We definitely had our expectations too high, so please consider this if you think about going there.

My husband and I recently spent 2 nights at Prospect Hill Plantation. We have traveled extensively, and have stayed in several inns in the Select Registry and been very well satisfied. Upon arrival, we couldn't help but notice landscaping. It has been very dry this summer, but there seemed to be no attempt at keeping it presentable. All of the planters around the property had either weeds or nothing in them, with a few exceptions of some very tired flowers in a few by the entrance. The landscaping was pretty overgrown. While the buildings are very old, they really needed some TLC. We stayed in the Boys Cabin (built in 1699). While it could have been charming, the interior seemed like it had been updated in the 1970's and nothing since. The bathroom had a wall mounted hairdryer that must not have worked because another one was next to it. The shower had a wall mounted soap dispenser that obviously had not been used in quite a while. We had a small, shabby porch on the back that overlooked the swimming pool, that also was pretty shabby. While the cabin was very old, it was in desperate need of a thorough cleaning. We noticed the fireplace was full of cobwebs.
On the plus side, we had a delicious dinner Friday night. The food was very good, but I couldn't help but notice a lot of the dishes were chipped. There was a complimentary wine reception before dinner. I asked the owner (who was serving the wine) if it was local wines, and he responded that Virginia wines had gotten more popular and expensive, so he was not serving them. The glass of chardonnay we were offered was bad (really bad, not just bad wine) so we did get another glass of a merlot that was ok.
The breakfasts were ok - we have been to several b & b's, and the breakfasts are usually wonderful. One morning was belgian waffles and sausage, the other a rather odd omelet with boursin herb cheese & sundried tomates, bacon and a muffin. Both days started with fresh fruit, that tasted like some of it had been frozen first, and also a glass of orange juice (not fresh). The coffee was good.
We paid $295/nite for staying here, which did not included dinner Friday night. I am sure the economy has hurt a lot of places, but even if we had paid half of that, i would not have been too happy. It was very disappointing - we debated on switching to a different place our second nite, but were concerned with being able to get a room as tit was a holiday weekend.