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The Winelands are sufficiently compact that you can make one hotel your touring base. Stellenbosch and Paarl, situated close to dozens of wineries and restaurants as well as the major highways to Cape Town, offer the most flexibility. Here bed-and-breakfasts and self-catering (with cooking facilities) options are often less expensive than hotels, and provide a better taste of life in the country.
Franschhoek is comparatively isolated, which many visitors consider a blessing. The West Coast, the Cederberg, and the Overberg are much more spread out, so you'll want to stay in one place for a day or two and then move on. During the peak season of December-January, book well in advance, and be prepared for mandatory two-night stays on weekends. Although the winter months of June-September are usually a lot quieter and bring negotiable rates, seaside towns get really busy (and booked up) when the whales arrive to calve. The same is true up the West Coast during flower season.