Chess house was the highlight of our Santorini experience. The view was breathtaking. The area is very quiet and peaceful. Although it is away from Fira and Oia, we actually enjoyed it more since we were not surrounded by hoards of tourists 24/7. The cave house experience was super cool and a must while visiting the island, but we wouldn't recommend it to anyone who is over 6 ft (the bathrooms are tiny), or anyone out of shape (we also counted and it is exactly 60 steps). We were a group of 5, average height, young adults so it was perfect and great value for the area. We liked it so much we spent one of our nights staying in and watching Mamma Mia. We feel so lucky that we were able to stay at chess house!!
P.s. If you're a larger group you should definitely rent a car. Katerina was super helpful and hooked us up with a car rental company that picked up and dropped off the car.