While reading your story, I remembered the time about 10 years ago when a prospective new boyfriend and I decided we should finally do a weekend together. We thought it would be cool to book a B&B or a room in a cute little hotel on the coast of Lake Michigan. We wanted sand dunes, waves, sunshine, nature, ... and the privacy to explore our relationship to see if we truly clicked.
I examined potential getaway sites by their outward beauty and suitability. He was more cautious, insisting we'd be really uncomfortable if the owners were unhappy with a gay couple sharing a room and a bed.
So we checked out gay publications in print and online to see who advertised. He figured that if a guesthouse was advertising with an LGBT publication, they'd be fine with us staying.
I know that tip isn't practical in every circumstance, but it worked out well for us. We stayed at a cute little place by the beach with about 20 cute rooms. While the place was not a gay resort, a couple other guests were obviously queer, and the staff were kind and helpful, even suggesting a local gay bar we might enjoy.
This might not feel unusual for folks used to big liberal cities, but this was rural western Michigan, where such a welcome is not usual.
I'm glad my friend suggested we take precautions!