OR allows you to get search results that include any of the items in the OR search list. That is, this search would turn up both overpriced hotels and, separately, overpriced bed and breakfasts in Montauk, rather than searching for some sort of monstrous hotel-B&B hybrid.
Finally, there’s the NOT operator. Let’s say you burned some bridges last time you were in Montauk. You could search: Montauk AND (hotel OR bed and breakfast OR B&B) AND “too expensive” NOT (“Jerry’s Hotel” OR “House Of Fragile Cups”) That would keep you from getting results that might remind you of the incident, and prevent your honey from trying to book with Jerry again. Ugh, Jerry.