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Thinking ahead a little here. I am planning to take my new dog (currently 4-mo pup) to the family cabin in another month or two, and that will probably be our vacation for this year.

But something I'd love to do next year is check out a nice paid hotel-type getaway where it's fun for the dog, too.

I have stayed in a hotel that allowed small dogs, but there wasn't much around the hotel that would've qualified as fun for either of us, so I guess I mean more of a cabin or resort or something more than just the place to sleep.

Any thoughts or suggestions?

Can you give us a region where you are thinking of going? I only know of dog friendly places in this world

Sorry I didn't specify locale, I'm in Central PA and would first consider something within a day's drive. The family cabin is 4.5 hours away by car, near Ithaca, NY, just as an example. I'm not ready to take pup on a plane trip just yet

So here in PA, also Michigan, OH, NY, NJ, Delaware, VA, WVA, probably other places I've never been beyond those states.

Nemacolin Woodlands resort in the laurel mountains has a pet spa. It is pricey but there are many packages at various times of the year. It is 4 season friendly with many activities.

Love this idea!!

I bet there are tons of cabins/beach homes in Michigan you could rent that would be pet friendly and then pup could play on the beach!!

Barkwells in Asheville, NC.

Asheville is a fabulous city and Barkwells is a great place to stay. We have stayed there several times and are always delighted.

I saw a lot of cabin rentals that were pup friendly in the Blueridge mountains. Beautiful places too. Do a search on VBRO and choose "dog friendly" to narrow your choices.
I think if you go that way you can find dog friendly rentals in many locations. I saw them in the Florida Keys and Lake George/Lake Placid as well.

I will be in the same boat as you soon
We typically go to Walt Disney World but cancelled this summers trip in favour of a puppy. We'll take him to my parents cottage that week instead.

I know Disney has a kennel with boarding but I don't think that's what you had in mind and that's not we'll do either. We're lucky in that my dog loving sister and mother in law have already offered to puppy sit for winter vacation