Cypress Inn, Carmel, Calif gets my vote. It is owned by Doris Day and a partner. I just returned from a trip to Calif , including 3 nights at the Cypress Inn.
There is only one small section of the Restaurant and Bar that is off limits. That keeps the Health inspector satisfied. Everything else is open to dogs. We ate breakfast every morning , in a nice dining area just off the lobby, and Gracie joined us. We had dinner 2 nights there, and Gracie joined us. We had drinks served in the Hotel Library, in front of the fireplace, and Gracie joined us.
A few times there were a few brief barking sessions in the dining room, as one dog welcomed another to dinner, but they didn't last long, and were rare. Everyone smiled and continued eating and drinking.
The Hotel was Very Clean.
Gracie was welcomed all around town. Many restaurants had nice patios, some heated, where dogs could join the family for a meal.
We travel a fair amount, and always miss Gracie the dog when we leave her at home. She did great on the Delta flight ORF-ATL-SFO, but we'd love to find as pet friendly a destination and hotel , closer to the east coast.
Loews Annapolis will always stick out in my mind. My dog was celebrated by every employee we met. Treated more like a rock star than a dog And they had a big cuddly house Lab, who was evident throughout the hotel. Chef made a special doggie stew that you could get via room service. At least once a month, they had a cocktail hour get-together for guests and local dog lovers with drinks on the patio, various activities for the pooches and it was always a fund-raiser for a worthy shelter or rescue group. And fun, too. I was putting on a dog adoption promotion for the Annapolis shelter and they sponsored our stay and provided Loews stainless-steel water bowls for the gift bags, as well as space to assemble and store the gift bags. I was very impressed by ever goll-dog aspect of the hotel. Lovely area to walk a dog, too.