What is the best style doghouse to build for a medium size dog?
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Here is a good plan with pictures. If you live in a cold winter area consider adding some insulation and straw in the winter for warmth. I built dog houses for my large dogs and placed them inside 8 x 10 kennels situated on cement sidewalk blocks so they could not dig out.
https://www.wikihow.com/Build-a-Dog-House
I recommend an A-Frame-Rectangle house would be sufficient. Your dog won't care. It's just shelter to him. Notice what your dog likes to lay on in the house & take that & put that into the doghouse. It already has his scent on it & he would adjust more quickly to his new doghouse. If desired, you could build one to accommodate both dogs at the same time so they'll feel more secure being together.