Registered with the Palm Beach Preservation Foundation as a historic landmark, the Chesterfield’s iconic white building has been used as a hotel since 1926. After a series of name changes—it was originally called the Lido-Venice—the property was dubbed the Chesterfield in 1989 when it was purchased by the U.K.-based Red Carnation chain. The hotel certainly has a British feel—particularly in public spaces such as the Churchill Cigar Room, where you can enjoy a smoke straight from the well-stocked humidor—but it’s truly pure Palm Beach, attracting Lilly Pulitzer–clad guests during both high and low season. Many of the 52 rooms are dressed in chintz and tartan and paired with modern streamlined furniture, and there’s a lush outdoor courtyard that’s a lovely place for a crisp Cobb salad with locally grown beefsteak tomatoes and a signature Courtyard pink martini. It feels more like a British estate than, say, an Art Deco hotel in South Beach—and that’s just how travelers like it.