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I'd recommend Trinidad, Cuba. The town has hundreds of "casa particulares" (bed and breakfasts) for anywhere from $25 or 30 a night to even $15 a night. You can take a cab to the Ancon Beach (about 20 minutes away), or stay at one of the beach-front bed and breakfasts at the hamlet of La Boca (also about a 20-30 minute cab ride from Trinidad). Trinidad itself is an 18th Century city with its architecture and streets intact from that century. For hiking, drive to Topes de Callantes, in the Sierra de Escambrey, about an hour and a quarter cab ride north. There, you can stay at any one of several hotels or motels, most with pools, and mountain trails (usually to some natural feature, like a waterfall and pool) start w/in walking distance. Also, I really enjoyed the town of Sancti Spiritus, about an hour-and-a-half NE from Trinidad. Stayed at the Rancho Hatuey Hotel, with swimming pool, restaurant and bar, landscaped grounds, off an access road 1 km from highway, and about 6 km. from the town itself. It is like a self-contained resort, but only $23/night (off season, but probably not that much more in-season). Sancti Spiritus is also a colonial town where the architecture has largely been preserved (but without as many tourists). A river runs through it, with picturesque bridge. Nice park in center, and a 7 or 8 block pedestrian street through the center of town. I loved this town so much I prolonged my stay there by several days this past Sept. and Oct. Have a great trip!