Pousada Forte da Horta
Located inside a 16th-century fort perched directly on the harbor’s edge, this atmospheric hotel offers rooms with balconies overlooking the military cannons positioned next to the fort’s walls. There’s a good-sized outdoor swimming pool with the same gorgeous views from the lounge chairs. Modern rooms are comfortable but a bit on the small side; the sea view rooms are the way to go. The on-site restaurant Sal & Pico serves lunch and dinner, and guests are also a short walk away from a large choice of tempting places to dine in Horta itself.