This can be a great idea, and lots of fun for everyone. There are several books available that list vacation spots, hotels, motels, and campgrounds where dogs are permitted. They may want to meet the dog in advance, especially if the dogs interact with each other at the facility. Trust your instinct. Dogs thrive on human contact.
Dogs are generally people creatures.
They crave human contact. Crating a dog is not cruel if done properly. The crate can be a safe haven for a dog for short periods of time, and it is especially useful during house-training. Crating your dog can be abused if it is used for punishment or to get the dog out of the way for hours at a time. The crate should never be used for punishment.