Booking a hotel is one of the most challenging parts of planning a trip to the Greek Islands. The local hotel scene is dominated by small family run hotels. Travel agents in Greece have a less than stellar reputation. And even when you find a good one, the fact that most travelers plan to visit many islands spread out across the country make it hard to work with any one travel agent. Typically an agent will have contacts and deals with a handful of hotel owners — that they aggressively promote —  but will be of little use if these are fully booked or not fit to your demands.

If you’re someone who needs (for peace of mind) to have a hotel booked in advance then hotelscombined is a great site for good deals and extensive listings.

How to book hotels at the best prices

Tips and tricks to finding and booking a hotel

—> If you’re traveling outside of the July and August high season, arriving on an island without a reservation and searching for accommodations on your own is a great way to save money. If you’re on a budget and need a room at the best possible price then this is the best way to go.

Almost all the islands have main towns (usually the port) that are very walkable and you’ll often be able to check out a half-dozen hotels in less than 20 or 30 minutes. If this plan sounds outside your comfort zone, you can book for your first night on every island and then find a better deal for the ensuing nights.

This type of flexibility fits great with Greek island hopping. If you don’t like your hotel, the town you’re in, or the island you’ve visiting, look for something else or jump on the next ferry heading to a neighboring island.

One caveat: If you’re on a very tight schedule with just a night or two on each island then searching for a hotel in this manner probably isn’t your best use of time.

—> Contact hotels directly. This is also a good way to find great deals. Travel agents and hotel consolidators are middle men and very rarely does adding a middle man to a transaction make for a better deal for the buyer.

A simple Google search will produce a couple dozen listings for hotels that should be easily contactable. (The reply time will obviously vary.)

If you see something from a different site that looks really appealing but out of your price range, simply do a search for the hotel’s name and the island it’s on, then send the hotel owners an email explaining that you saw the hotel for such and such a price and wonder if they could offer a better deal. The more days you book the better the discount will typically be.