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Santorini is pricey and finding an affordable hotel can be a challenge. When we booked our trip for early June, to be honest, we were shocked at just how expensive it could be. Think hotels in the $1500 a night price range. My advice is book for mid may or early October. You'll save TONS and still have great weather. We only went in June because we had some friends that invited us along and had already booked their dates. We decided a hefty price tag for spending a few days in Santorini with friends was sooo worth it...and we were right!