The hotels that you are speaking of, are on the island of Santorini......
Will you spend your 4 nights there? Where will you be coming from and where will you go next?

Most likely you will have to fly via Athens, have you taken this extra time into consideration? UNless you fly directly from Santorii to somewhere else, it will be advisable to spend the last night in Athens, just to have a buffer zone in case of a winds, delays or strikes.

From the 2 hotels that you mentioned i would recommend Atrina Houses, for being in a real village with real people.

Oia is the nicest village of the island, and there will be plenty of restaurants, cafes and nice shops, unlike Imerovigli ( the location of the other hotel)

Anastasis Apartments are not even located in the village of Imerovigli, but as i read on their website 20 minutes away by foot... Imerovigli i like less, for being an artificial place with many hotels, but no real people living....

Most amazing photos you have seen of Santorini were shut in Oia... this should give you the idea

Thank you for the response! Yes I should have mentioned these hotels are in Santorini. We will be flying from Boston into Athens on a Monday and then connecting to Santorini. Then we will fly out to Rome on Friday Morning, so we will only have 4 nights, but really only 3 full days. We are considering adding an extra night potentially.

You're both right.

Anastasis is in Imerovigli where you would have the best overall sunset/caldera views but there is a very small variety of shops and restaurants there. Fira, where all the best nightlife is located as well as an abundance of shops and restaurants, is about 1.5 miles away. You can walk there but walking back is all uphill. Of course there are buses and taxis available.

Atrina is in Oia where there are lots of shops, galleries and restaurants to choose from with easy walking distance. It's also the most beautiful and romantic village. Oia's nightlife is limited to a few mellow bars and cafes but the sea views are still wonderful. There will be lots of busloads of cruise ship passengers coming to Oia as part of their land tour of the island, so Oia gets almost as busy as Fira for a couple of hours in the morning and right around sunset.

Thanks for the information!

I think I am just torn between the value of being right in OIA vs the value of the Anastasis Apt which looks so beautiful!