Chester Inn

note that there are new owners, so all reviews prior to this do not apply to the new owners (complaints about service in past reviews). not sure I'd stay here longer than one night, as it was directly on main street in the center of town, and a little busy for me. great for one night. the place is clean, furnishings nice, and new owners were helpful. I did not stay long enough to make a judgement about the overall service,. the only concern I had was the fact that this place is directly on Main Street, which is a major truck and commuter route and the trucks started rolling at 4:30AM. Prior to that it was dead silent between the hours of 8pm-4am. Also the house is occupied by a few long term residents, so it did not have that cozy comfort touristy vacation feel to it. Overall, h

We had an incredible snowy weekend. The parking lot was easy to access and the path was clear of ice. The room was warm,cozy, and spacious. Alli and Tyler answered all my questions with grace and kindness. The kitchen was respected and the residents were respectful of eachother. The Scottish pub and bakery within walking distance were highlights and the check in and out processes were simple and flawless. Incredible weekend away skiing with my fiancé. We will most definitely be back.

We enjoyed our stay at the Chester Inn which is a historic inn located across the street from some quaint stores in the town of Chester. Communication with property management was easy which allowed for easy entry on your own to the property and your room. A room key was left in your room but the lockbox next to your door with an additional key was great especially when you accidentally locked your key in your room!!! In addition to your room, there is a lovely sitting area along with a dining area and kitchen where you are welcome to use the toaster oven and dishes to make yourself breakfast or snacks. Coffee, tea, hot chocolate, and oatmeal is provided. Our room with a fireplace was well appointed including a coffee pot and coffee, a microwave and a refrigerator with a tray of ice cubes

We LOVED our spacious room and private bath during our 2 night Feb 2026 vacation. bedding & amenities in the room were excellent and cozy sitting area downstairs. walked across the street for dinner which was so convenient. 20 min drive to Okemo is the reason we chose this Inn

We had a great stay at the Chester Inn for a long weekend. Tyler and Alli were super responsive when needed. The room (#5) was spacious and comfortable and we were never without hot water!