Chester House Inn

Definitely not worth the nightly rate. I picked the Chester House because of its location on the way down Scenic Route 100, figuring it for a good place to rest between Stowe and Boston. Reviews on Unilocal and trip advisor gave me the impression of a sleepy (quiet) country town. But it’s not. It’s a main thoroughfare with loud trucks all through the night. But if that doesn’t keep you up, the slamming doors, and creaky floors will.
That being said, besides the bathroom spider and his cousins spider web behind the beds, it is a fairly charming b&b. The room was big enough for mom, dad, and 3 kids. Breakfast was very good, but way too much food for the kids. And they charge for it (pp fees), so don’t feel guilty when the kids leave 90% on the plate. I tried being thoughtful by warning him that the kids wont eat all the great food, but felt like I was bothering him.
My biggest disappointment was not the noise or the spider webs, or the nightly rate. Rather, it was the inn keepers. I hate saying that, because you always want to like the ma and pa that run the joint. But I just felt like they really don’t like their retirement career. While very accommodating and cordial, one cannot shake the feeling that you are a burden to take care of. Not a lot of personality, or the kind of personable warm welcome you expect from a b&b.
To top it off, I made my reservation online for four people, knowing my little one wouldn’t need his own bed. I then talked to Bob on the phone and told him so. He said the 5^th person is an additional $ 29 because «he’s gonna eat isn’t he?» I responded by telling him he hardly eats, but its perfectly fine to charge the additional amount. Bob said, «Well, if he doesn’t eat a lot, I’ll let it slide.» «Are you sure, I said. Please do whatever is appropriate.» He said «it’s okay,».
Cool, off to a good start. He even set up an extra bed for my little guy, which was a nice surprise. Unfortunately, while I’m packing up my car the next morning, he gives my 10 year old the bill and tells him to tell me I owe $ 31 for the 5^th person and reminds me thatI I only made my reservation for four. I don’t have a problem with the extra $‘s… but to give it to my kid… that was the most disappointing part of our stay… and just as we were leaving.
Horrible way to end a so-​so experience when I was still trying to find the bright side of the Chester House, so I could remember it with some fondness.

The Inn was well kept, the room was cozy, the amenities were just right. The breakfast was excellent, and there are fresh baked cookies every day. The owners were beyond friendly and helpful.
This Inn is a short drive (15 min?) to Okemo and is located in a quaint town with a few restaurants within walking distance.
The rooms have a range of prices, and we stayed in one of the more expensive ones and I thought it was definitely worth it — hot tub, fireplace, bathrobes. It was perfect.

My wife and I stayed at the Chester House Inn while on a bicycling weekend in Vermont. It is a beautiful old inn, extremely well maintained. While the original part of the inn was built in the late 1700’s, it has been modernized tastefully. The living room features a huge fireplace which I imagine keeps the place nice and warm in the winter.
The inn keepers were very friendly and helpful in pointing out some of the better places to ride our bikes in the area. They were also very helpful in recommending some of the better restaurants in nearby Ludlow. The breakfasts were also very good. The food was plentiful and healthy. If we ever find ourselves in that area of Vermont again I would be happy to go back.