Find Dog-Friendly Hotels in Chester, VT

"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!"

"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."

"Overall decent room, spacious for the price, and bonus that it is pet friendly. I would stay again if I had my dog with me and was going to be out hiking and just needed a place to sleep."

"Great value "

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

"There was only one person able to check in people when we arrived before the big eclipse; it took over an hour to check in. We were told a worker was sick, but it was disappointing that there was not another staff member able to independently check in people. The hotel did make it up to us when we asked, but it was an unwelcome experience."

"The hotel was absolutely lovely. Spotlessly clean & the staff were so friendly & I loved that it was dog friendly. Also there are fire pits which you can use at night. We had a delicious breakfast in the hotel restaurant. ⭐️⭐️⭐️⭐️⭐️"

"Historic and comfortable country inn in the heart of charming Woodstock, and Red Rooster, their main restaurant, features the best dining in miles."