4 Best Sights in The Southeast, England

It's hard to imagine a more romantic castle than this: a maze of turrets and battlements encircled by a water lily–bound moat filled with fabulous beasts (enormous Japanese koi carp) and nestled within rolling hills. The childhood home of Anne Boleyn, this is where the second wife of Henry VIII and mother of Elizabeth I was courted by Henry. He was enamored with her for a time but had her beheaded in 1536 after she failed to give birth to a son. He then gifted Boleyn's home to his fourth wife, Anne of Cleves.

Famous though it was, the castle fell into disrepair in the 19th century. When American millionaire William Waldorf Astor acquired it in 1903, he needed additional space to house his staff. His novel solution was to build a replica Tudor village, using only methods, materials, and even tools appropriate to the era. The result is more or less completely indistinguishable from the genuine Tudor parts.

Astor also created the stunning gardens, which today include a wonderful yew maze, ponds, playgrounds, tea shops, gift shops, plant shops—you get the picture. There's a notable collection of Tudor portraits, and in summer, activities are nonstop here, with jousting, falconry exhibitions, and country fairs, making this one of southern England's most rewarding castles to visit. In one of the Victorian wings, B&B rooms go for upwards of £175 per night for a basic room; there's also a four-bedroom holiday cottage available for £4,150 a week.

A grand Victorian mansion with a pond-dotted estate offering views over the surrounding countryside, Chartwell was the beloved private home of Sir Winston Churchill from 1924 until his death in 1965. Virtually everything has been kept as it was when he lived here, with his pictures, books, photos, and maps. There's even a half-smoked cigar that the World War II prime minister never finished. Churchill was an amateur artist, and his paintings show a softer side of the stiff-upper-lipped statesman; outdoor art trails show his work displayed at the points where he likely sat to paint them. Admission to the house is by timed ticket available only the day of your visit. To get here from Hever, head north on the B2027 and follow signs. Be sure to explore the rose gardens and take a walk in the surrounding countryside.

At the center of the adorable hamlet of Penshurst stands this fine medieval manor house, hidden behind tall trees and walls. Although it has a 14th-century hall, Penshurst is mainly Elizabethan and has been the family home of the Sidneys since 1552. The most famous Sidney is the Elizabethan poet Sir Philip, author of Arcadia. The Baron's Hall, topped with a chestnut roof, is the oldest and one of the grandest halls to survive from the early Middle Ages. Family portraits, furniture, tapestries, and armor help tell the story of the house, which was first inhabited in 1341 by Sir John de Pulteney, the very wealthy four-time London mayor. On the grounds are a toy museum, a gift shop, and the enchanting 11-acre walled Italian Garden, which displays tulips and daffodils in spring and roses in summer. Take time to study the village's late-15th-century half-timber structures adorned with soaring brick chimneys. To get here from Hever, take the B2027 east then follow signs to Penshurst.

A well-preserved family country house dating from the 1890s and set in a beautiful hillside garden, Standen typifies the Arts and Crafts movement. Designed by the influential architect Philip Webb (1831–1913), it contains a wealth of William Morris carpets, wallpapers, fabrics, and even original electric-light fittings. Look out for the particularly beautiful Mother of Pearl cabinet. The house is 12 miles southwest of Hever, just across the Kent–West Sussex county line.