The Best Hotels to Book in Cortona, Italy

This pink-hued 17th-century pile majors in slow food and excellent wine, set against the bucolic backdrop of the Chiana Valley hills. It’s a glam affair: nine rooms of whitewashed beams and terracotta-tiled floors. Take a tour and tasting of the cellars, lined with barrels of cabernet and syrah, made from grapes fed by the clay-rich soil. The microclimate is a blessing – you can laze by the pool or day-trip to nearby Montepulciano, home to the bell towers visible from the Villa.

Make the glorious emerald pool your first port of call on reaching this fine 19th-century stone villa. Next, unpack in your rustic-chic room, two-bedroom suite or apartment with kitchenette – you’ve arrived. Expect lazy days sipping wine from the cellar, on one of the many stepped terraces, admiring the view of the hills. There’s nothing to stress about, but you might want to book a massage in a space near the pool. Eventually, you can drive the 7km (4mi) to marvel at the Duomo di Cortona.

A few days’ stay in this 15th-century vine-clad manor house in the Tuscan hills is pure indulgence. The place has pedigree, once the hunting lodge of Cardinal Passerini, who was loved by the Medici banking family/political dynasty. There is little to do other than stroll from your room, with its muted tones, to the sun-warmed pool. Or borrow a bike and explore the landscapes – you’ll be feeling super-fit thanks to the hotel-garden vegetables they serve, along with wild boar.

Check in at this 15th-century palace, in the historic heart of Cortona, for a holiday that’s grand yet cosy, all terracotta-tile floors, chintzy furnishings in regal reds, ornate bedheads and fancy rugs. Rooms range from singles to suites with bathrooms big enough to live in. The icing on the cake is the 15th-century tower-turned wellness area with hot tub: go double-bubble with a sunset prosecco, gazing over the romantic Tuscan landscape before a nightcap in the pretty bar.

The idea is to take very things slowly at this relaxing 17th-century farm villa. It is set in tranquil grounds of stone-paved paths, laden with fruit and olive trees. There’s an irresistible outdoor pool, flanked by smart loungers and parasols. If you’d like a little light exercise, go exploring the trails that lead to Cortona. The 14 rooms and five apartments are nicely meditative, with their tall vaulted ceilings.

This 17th-century mansion is an elegant affair – part villa, part chapel, part cottage, immersed in olives and vineyards in the Tuscan countryside 3km (2mi) from Cortona. Rooms, in a pretty palette of blue and white, come with grand marble bathrooms, while posh beds overlook the garden or the slopes beyond. Special occasion? Book the Winery Master Suite, with its vineyard-view terrace. And to aid relaxation further, there’s a spa and a Michelin-star restaurant.

An easy-going elegance prevails at this country house hotel, where rooms ooze style with white walls, terracotta-tiled floors and oversized damask headboards. For top privacy, try the junior suite, Diamante, in a cottage with a terrace looking across the Val di Chiana. Sunbathe around the pool in the gardens, framed by hills and olive groves rolling away to nearby Cortona. Inspired by dinner? Learn to whizz up stuffed tomatoes and pasta al ragù at a cookery class.

A 10-minute drive from Cortona, step back in time at this sprawling 18th-century estate. With its atmospheric rooms of exposed timber beams and stone arches, it’s a place for snoozing and lazing: the lush garden has a shady gazebo with views of vineyards, olive groves and Tuscan hill towns. For golfers, several clubs exist within a half-hour drive, but we’d rather settle in for relaxed dining poolside, then an in-room massage in our Spa Suite, with its hot tub for two.