10+ results in the Western Cape
The Western Cape has the widest spread of small hotels in the country, and they sort roughly by landscape. On the Peninsula you are choosing between the Atlantic seaboard, the city under the mountain, and the old wine valley at Constantia. An hour inland, the Winelands put you on working estates where the wine and the food are the point. Further out, the Overberg, the Karoo and the Garden Route trade restaurants for space.
The character changes with the setting. A townhouse near the city puts galleries and dinner within walking distance. A Franschhoek or Paarl estate is a place to stay put for a few days. A Karoo village hotel is a stop that turns into the part of the trip you remember.
Most of these stays are request to book. You send your dates, the hotel confirms, and you pay in rand, with no guest service fee.
Both, if you can. Cape Town is best for the beaches, the mountain and eating out. The Winelands are better for a slower few days, and Franschhoek is a little over an hour from the city, so splitting the stay costs very little travel time.
December to February is warm, dry and the busiest time of year. March to May is still warm, quieter and harvest season in the Winelands. Winter, from June to August, is wet in the southwest but green, and it is when small hotels are easiest to book.
Yes. The Overberg coast has whales from roughly June to November, the Karoo has some of the clearest night skies in the country, and the Garden Route has forest, lagoons and beaches. Each has small hotels that make a good base.