Elizabethan House

Elizabethan House works well for families or groups wanting a proper base rather than a cramped rental. The four bedrooms and two bathrooms spread across three floors give everyone room to breathe—a king bed with ensuite, two singles, a double, and a single room mean flexible sleeping arrangements for seven. One dog is welcome. The whole place is yours alone, with free parking outside and enclosed front and rear courtyards to decompress in after a day out.

This is a 17th-century listed building that's been refurbished without losing its character: exposed stone, stripped wood floors, and timber beams throughout. Downstairs you get a living and dining space with a woodburner, plus a kitchen equipped for proper cooking—gas hob and oven, dishwasher, microwave. Essentials like heating, linen, towels and wi-fi are all covered. A cot and highchair are available if needed. Note that the stairs are steep and narrow in places, and there's one step at the entrance.

Portland sits 500 yards from Chesil Beach, the 18-mile shingle stretch that hosted Olympic sailing in 2012. Weymouth's traditional seaside attractions—amusements, restaurants, Sea Life Park—are a 15-minute drive. Locally, pubs and cafés dot the area; Quiddles Cafe is within reach. Portland Harbour's sailing waters are minutes away. No smoking throughout the property.