Krone Regensberg is everything you want from a boutique hotel in a small medieval hilltop village. It’s been an inn for the better part of eight hundred years, but these days, the meticulously preserved timber exteriors betray not a hint of the luxe modern interiors that await inside.

Seven linked buildings comprise this spectacular property in Prague’s picturesque Malá Strana. The hotel’s oldest building, the Augustinian St. Thomas’s Monastery, dates to the thirteenth century. Several monks still live nearby, sharing the landscaped paths with guests, but these days things have gotten quite a bit more comfortable.

The Royal Abbey of Fontevraud isn’t just a popular tourist site — it’s a hotel as well. Set on the sprawling 12th-century complex where Eleanor of Aquitaine once lived (and where Richard the Lionheart is buried), Fontevraud L’Hôtel enables guests to see this historic and architectural treasure from a whole new perspective.

There’s no escaping the past in Venice; even the Venice Venice Hotel, dedicated as it is to “postvenezianità” — post-Venetian-ness — finds itself in the 13th-century Byzantine-style Palazzo Ca’ da Mosto, overlooking the Grand Canal and the Rialto Bridge. Its owners, however, have their sights set squarely on the future.

Spending a few nights at Viguier du Roy, in the riverside medieval village of Figeac, is a wonderful way to immerse yourself in French culture. From the charming stone courtyard to the decorative toile wallpaper, this boutique hotel — formerly a luxurious private residence — is grounded in seven centuries of local history and tradition.

Celebrity guests come and go, but it says something about Hacienda Zorita Wine Hotel & Spa that the name they drop most is that of Christopher Columbus, who paid a visit to this one-time monastery near Salamanca on his way to the New World just over half a millennium ago.

Perched on a hilltop surrounded by gently rolling hills, the Castello di Vicarello is an authentic 12th-century Tuscan castle, converted into a charming country house boutique by a couple of fashion types who moved down from Milan in search of the quiet life.

Time has a way of softening things; so it is with medieval castles converted into romantic getaways, like the lovely Pousada Castelo Óbidos. There’s quite a colorful history here involving falconry, fierce battles, and child brides. The castle had its moments back in the 13th century, but it’s quieter, and altogether more romantic, today.

City-center boutique hotels don’t get much greener than the Botanic Sanctuary Antwerp, set within the walls of the city’s botanical gardens. Here a monastery complex, some of whose buildings date back as far as the 12th century, has been transformed into a 21st-century luxury hotel, alongside a spectacular modern spa.

Set on a vast estate in the picturesque hills of Umbria, Castello di Reschio dates back all the way to the tenth century, which makes the decade-plus its owners, an architect and an artist, spent on careful restoration seem like the blink of an eye by comparison. Given the results you’d have to agree it was worth the wait.

If what you’re after is a picturesque medieval town, criss-crossed with canals, you should know that Bruges out-Amsterdams Amsterdam by some distance. And only in Bruges could you find a hotel like the Relais Bourgondisch Cruyce, which occupies a pair of gorgeous, delicate old timbered houses.