I will be traveling to Santorini for the first time in May- arriving May 7th. I am looking for accomodations for 4 nights, two people. We are looking for a hotel in Oia for around $100 per night. We do not need a pool but would love to have a private terrace with good views in a convenient location. Cleanliness is very important.

We will move to Naxos for 2 nights before returning to Athens. Suggestions there would also be appreciated. I have always been very pleased with the responses on this forum and look forward to your thoughts on the matter.

Check Delfini Hotel, Villa Kallisti, Casa Sofia, Thea Studios, Fotinos Houses and Stelios Rooms.

On Naxos focus your hotel search on St. George Beach.

Depending on how when your arrive on Santorini you may want to consider just getting to Fira and trying a walk up approach. Many of the hotels will have just finished 6 months with no cash flow and their rack rates mean nothing when they are empty in the pre season. It is very possible you can get a great price in a good hotel in early May. On the other hand if you arrive later at night no one is likely to negotiate with you.
In Naxos I totally agree with Brotherlee. St George is the place to be. It is on a good beach but just adjacent to Naxos town where you will find lots of activity, shopping dinning, a lovely waterfront and some antiquities. You get the best of a beach locations and the city attractions but it is quiet at night for sleeping. There are lots of good hotels in St George. We always stay at hotel Glaros which is a small simple family run hotel. There are better more expensive options nearby including Naxo Resort Beach Hotel which should cost around 120 euros a night whereas Glaros is a budget hotel at around 60 a night.
Here are some pictures of Naxos
http://travel.webshots.com/album/552001505EYxVYT
Have fun planning.

I've stayed at Stelios Rooms in Oia and wouldn't recommend it.

In St George on Naxos I've stayed at Argo Hotel http://www.argo-hotel.gr/ several times, and it's fantastic value for money. The hotel is one street away from the beach, and ten minutes walk into Naxos Town. The hotel is run by a very friendly Greek-Swedish family, is immaculately clean, and has spacious rooms with good showers. Last time I stayed there (in June a few years ago), I paid €20/night plus an optional €5 for breakfast.

We stayed at Old Oia houses in Oia although we opted for a bigger house which cost a few EUR more, it was worth it for the extra space. It is run by an English lady and her Greek husband, they have several properties, the one we stayed, if my memory is correct, is opposite Zoe's Houses but they have other accommodation near to the Museum hotel. The location of our accommmodation was better IMO. Some of the rooms were quite near a main path, I would recommend asking for a room lower down the terrace as they are more private esp during the evening rush to see the sunset.

The terrace had a fabulous caldera view, the room had a kitchenette, large seating area, a separate bedroom and bathroom (carved into the rock), essentials were provided eg coffee, fruit juice and fresh bread was delivered every morning, although I went to the bakery as I didnt like the bread.

The rooms were cleaned every day, bedding and towels changed every other day. Location was very good, right in Oia and not far to walk to see the sunsets and walk down to Amoudi, not far from parking, bus stops or restaurants.

Since you are going in May, I would look to higher category accomodation eg Delfini since it might come into your budget in low/mid season.

Thanks, I'll start looking at your suggestions!

Check Lava Oia www.lavaoias.gr

Quaint accommodations, large terrace with beautiful views, a short walk to center of town which was nice because it was away from the crowds.

I second Lava Oia's. We stayed there and loved it! Pepitsa, the owner, is an architect and she bought and refurbished these cave houses. She's a wonderful host. It's in a quiet area with gorgeous views. I would think you could get one of her smaller houses for that price since it's the off season.

A lot of the suggestions are very good though.

In Oia, look at hotel LAUDA; Never stayed there, but good reviews has a pool ... I took a good look at it when I was in Oia last May. I think it was around €100 ($129 currently) ... and VERY handy... if I wanted to stay in Oia & had the $129, that would be my choice - http://www.lauda-santorini.com/

We stayed at San Georgio Villas [www.sangiorgiovilla.gr/ E-mail: [email protected]] 50€ night/ double. Wonderful place to stay in Fira. Clean, nice size rooms with AC, fridge, TV, free wi-fi, hairdryer. George arranges pick up and drop off from airport or ferry port (extremely useful since finding it for the first time would be challenging). It’s on the other side of the main road from the caldera and the labyrinth shopping streets but still only a five-ten minute walk to the caldera, the bus station, etc. George is extremely helpful and gives loads of accurate info on where to go and what to do. There is no caldera view obviously, but there are plenty of places to view the caldera for free. We had a tiny balcony where we had our Greek yogurt and fresh fruit breakfast each morning. There were plenty of places within five minutes walk to buy groceries like this for breakfast and snacks.

Naxos – Anixis Hotel, www.hotel-anixis.gr [email protected] 45€ (breakfast available for 5€ per person). Very nice hotel in a great location ONCE YOU FIND IT. Which is incredibly difficult to do. It is deep in the labyrinth of stepped tiny arcaded corridors that are called “streets” in Naxos. Delightful to wander around, but not with your bags (and we only had one 18 inch each) looking for a hotel. They need to either give guests good directions or mark it better. Once there, the rooms are spotless, spacious and have TV, AC, Fridge, and your own terrace. The rooftop terrace (where breakfast is served) is available all day and has great views of the cathedral and whole town including the portara. They do have free wi-fi too but the signal strength was usually so low that it didn’t work. Here’s how to find the Anixis – from the promenade along the harbor enter the old town where it says “old market” and then look for signs for Hotel Panorama which is very well marked. Just keep following those signs till you are in front of the Hotel Panorama, then look past it one street to see the sign for the Anixis. Alternately take the road (car road, tiny sidewalk) from in front of the ferry dock a couple of blocks till you see the grocery store/fruit market, and bear right which brings you to the cathedral in another half block. From in front of the cathedral enter the old town, go up the steps to the next tiny square where you have to turn right or left – turn right, immediately left, next left, next right and it’s just ahead. Each of these turns is about a half minute walk.

These are from my trip report which is at - http://www.fodors.com/community/euro...rip-report.cfm