Find ski hotels & lodging in Chester, VT

"The town is super small and the rooms are clean but very outdated. It felt like camp 🏕️ which was what we were looking for. The pool and hot tub was amazing! I wish the rooms were more updated but overall it was great!!!"

"I enjoyed my stay at the Shire. It’s an odd mix of comfort, luxury, bargain and practicality. The room was clean and comfortable, if a bit worn. I sprang for a river front room, which was an excellent idea. The deck outside my door was right off of the lawn at the edge of the water, and it was a delight to have the soothing water sounds outside. In better weather, you can use the fire pits and Adirondack chairs to create a cozy vibe at the water’s edge. The drawback to the waterfront rooms is that you have to navigate a steep, rough staircase beside the building. The hotel’s location just minutes from downtown Woodstock was perfect. I even walked comfortably to Billings Farm, one of the town’s major sights. Be careful about closures out of season — many restaurants and shops were closed while I was there. But there’s a grocery store across the street that has a deli and prepared food. There’s a nice park (a reclaimed landfill) almost next door, with natural playground equipment and a walking trail. I visited friends at a higher-end resort down the street; they had an onsite restaurant, but I think my setting at the Shire was nicer!"

"easy parking"

"Amazing we arrived after business hours and they left the key and a note outside so we could get in when we arrived. The continental breakfast was great. Room was clean and well kept."

"My family enjoyed our stay very much! The outdoor pool and hot tub was a real treat before heading north to see the eclipse. My kids haven't stopped talking about our trip to Vermont! We will be sure to come back."

"Really loved the whole experience!"

"Great value "

"The staff were super friendly and really made the week worth while"

"It is an excellent ski hotel with friendly service and great beds. "