When dreaming up weekend trips to Boston with Orvis, The Liberty Hotel has always been high on our list of places to stay. Friends of ours with dogs have long talked about how accommodating the hotel is to pets, especially on Wednesday evenings in the summer during the famed Yappier Hour. So, when we found out that I’d be speaking at a conference in Boston this past weekend and decided to bring Orvis along for the trip, we looked no further than The Liberty.

Housed in the former Charles Street Jail, The Liberty Hotel is easily one of the more unique settings in which we’ve ever spent the night. The stylish open main space, in the old jail’s central octagonal building, retains many of its original 19th century architectural details, including the cells inside Clink, the catwalk walkways, and the wrought-ironwork on the windows. But while the details are a constant reminder of the space’s past criminal “guests”, a night at The Liberty is far from a stint in The Slammer. The modern amenities, the comfortable rooms (many with amazing views of Beacon Hill and the Charles River), and the impeccable service are just a handful of reasons why we’ll be returning in the future, but possibly the greatest asset of The Liberty for our trio was just how dog-friendly it turned out to be.

We don’t always choose to bring Orvis along with us when we travel to cities – he’s always seemed to be happiest running wild in the country – but we couldn’t have been more pleased that he made the trip down to Boston. Walking around Beacon Hill, down to the South End, up and down Comm. Ave, and through the Public Garden with him at our side was something we’ll always remember fondly. From our research and the comments of friends, we expected a certain level of dog-friendliness at The Liberty prior to our arrival, but we were continually blown away by how well he was treated, both by the staff and by the other guests throughout our stay. He was encouraged to sit right next to us as we sipped our cocktails in the lobby bar, something which we rarely have the chance to experience with Orvis indoors. The image of a rather large, goofy dog in the middle of such a luxurious setting will always bring a smile to our faces, and we honestly cannot imagine planning another trip to Boston with Orvis that doesn’t include a stay at The Liberty – we all enjoyed ourselves way too much to not have an encore visit.

Photos taken by Meredith Perdue for Map & Menu.