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Cortona is in a great position, overlooking some of the most beautiful views of Tuscany spread out in all directions below it. Cortona's streets are steep and narrow, so this is a town best explored on foot. Some of the our Guru's recommendations for the best places to stay in Cortona are actually outside the town, but they offer similarly wonderful views over vineyards, olive groves and more beautiful hilltop towns. And that's the really incredible thing about Cortona, there are just so many beautiful rooms with views.
The Piazza della Repubblica is probably the most famous square in Cortona, and a good place to start your explorations. The Piazza Signorelli is right next door, and this is where you'll find the wonderful Sunday flea market and antiques fair, and Cortona's theatre.
You should also see the churches, but that's really a given in Tuscany, the main ones being the Duomo, the Eremo Le Celle a Franciscan hermitage, the Basilica de Santa Margherita - right at the top of the town, and the Chiesa de San Domenico, a 15th Century church home to some wonderful artworks.
Cortona is a great place for walkers - especially those who enjoy a hilly challenge. In the surrounding region you can stroll the old Roman roads of Torreone or Monte Maestrino, or just walk among the vines, and stop for a glass of Chianti in the vineyards dotted around the hills.
Don't forget to book early if you want a bed in one of best places to stay in Cortona during the busy summer months - the town is absolutely heaving in July and August. But if you plan your visit in May, June or September, you'll still have lovely weather (probably better because it won't be so hot), but the streets will be your own.
- Il Falconiere is a one of the best hotels in Tuscany, a haven of fine antiques, beautiful views and a Michelin starred restaurant. The 22 rooms are spread within the main building and a collection of private outbuildings surrounded by picturesque grounds, vineyards and olive groves.
- Fontelunga Hotel & Villas is a wonderfully traditional red Tuscan villa with stunning views from its collection of nine rooms and suites, and from the sunny terraces and beautiful grounds. There's also a pool and tennis court if you'd rather stay home for the day.
- Now a relaxed, family-friendly hotel the Villa di Piazzano begun life as a hunting lodge belonging to the Medicis. A perfect Tuscan retreat within a short distance of many local highlights the Villa de Piazzano also has its own great restaurant and lovely grounds.
On a budget
- The Relais Villa Baldelli is a 15 room villa just outside Cortona. It's a striking building with an enormous pool and wonderful sun terrace and garden. And it also offers cookery lessons and wine tastings. Rooms start at under £90 per night.
- The Relais Villa Petrischio is a stunning country house hotel in the hills of Chianti. Square and stone, but very cosy inside, this is a wonderfully traditional villa with a collection of 18 rooms, suites and apartments. Prices start from just €140 per night B&B.
Still not sure which to book? Browse through our list of all the best places to stay in Cortona, or contact one of our friendly Gurus for advice. Alternatively widen the net and check out all our recommendations in Tuscany.
Best Hotels in Cortona
Relais Villa Petrischio 18 rooms from $109Cortona,, Tuscany
A stunning country house set in the hills of Chianti. Traditional and cosy interiors have wooden beams, brass bedsteads, stone floors, and antiques. A selection of rooms, suites, and apartments. Fabulous views from the pool area, restaurant, and bar. Cooking lessons and a large wine list.Views - Stunning views over the Valdichiana hills.Families - One apartments sleeps 4.Country EscapeSights nearby - Tenuta Valdipiatta and Church of S. Francesco.
Relais Villa Baldelli 15 rooms from $113Cortona
A striking country house hotel just outside Cortona. Plenty to do; expert cooking lessons, wine tasting, sunbathing by an enormous pool, or strolling through the gardens. Dreamy rooms and suites are traditional and decorated with romance. A great choice for a couple as well as foodies.Romantic Break - Sunbathing, cooking lessons, wine tasting, and general relaxation.Romantic - Stunning rooms and serene surrounds make for a romantic spot.Views - Great views from hotelCooking classes - Excellent cooking classes to discover the roots of the regional cuisine.
Villa di Piazzano 21 rooms from $203Cortona (Tuscany)
This former Medici hunting lodge is now a magical Tuscan family-run hotel. Retreat to the romantic rooms, relax by the pool, stroll around the beautiful gardens, and feast on delicious Tuscan food and wine. The perfect country escape for all to explore Tuscany. Foodies will love the cooking classes.Great walks - The Umbrian countryside is simply stunning and offers plenty of walking trails.Sights nearby - Hop in the car to Lake Trasimeno. Take a picnic and make a day out of it.Cooking classes - Cooking classes avalaible for all guests. Enquire before arrival.Swimming Pool - Outdoor Pool
Fontelunga Hotel & Villas 8 rooms from $205Pozzo della Chiana Arezzo, Tuscany
Attractive red brick Tuscan villa with stunning views. Sun-soaked walls and terraces, contemporary designed rooms and suites, plus swimming pool and tennis court. Great for couples or for groups to rent exclusively.Sights nearby - Plenty of Tuscan hilltop towns and villages in the surrounding areaViews - Panoramic views across the countryside to CortonaSwimming Pool - Outdoor pool set amid the olive grovesDesigner - Uniquely designed interiors.Recommended by - Mr & Mrs Smith, Tablet, I Escape
Il Falconiere 22 rooms from $492Cortona, Tuscany
Romantic setting for food lovers. Dine at a Micehlin-starred restaurant in a stunning 17th Century Tuscan manor. Beautiful, spacious rooms are a perfect blend of homely meets luxury. Relax by the pool or at the spa. Dining is top class plus you can take part in cooking classes and wine tasting.Sights nearby - Take a picnic to Lake Trasimeno and spend a summers day in the water.Cooking classes - On site cookery school, led by Chef and owner Silvia Baracchi.Swimming Pool - Indoor PoolFull of characterRecommended by - I Escape, Tablet, Relais & Chateaux