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Some of our most characterful hotels are also some of our smallest hotels: historic Tuscan villas with Neo-classical gardens; boutique stays with individually decorated rooms; family hotels that run on Italian hospitality; rural trulli and masserie farmhouses; and even a sassi cave dwelling kitted out with modern minimalist furnishings. 

Browse our collection of small and boutique hotels to find a place that really gets you under the skin of Italy. They’re scattered all over the country, so you could wind up bedding down anywhere from sky-high Ravello to the deep south of Sicily.

 

The Hotel Villa La Vedetta is a boutique stay with some seriously luxurious extras, including a pool and terrace with views over Florence. 

The Hotel La Conca Azzurra is a showcase of local produce. Expect Vietri ceramics and dinners cooked using oil from the in-house olive groves. 

Mediterranean villa Botanico San Lazzaro has nabbed a hard-to-beat spot on the hillside above Maiori. Wide-angle bay views are a given. 

The Hotel Toro is more of a guesthouse than a hotel, thanks to the warm welcome that’s been extended to guests ever since the Schiavo family rolled out the red carpet in the 19th century. 

With its historic locale and vaulted dining room, the Hotel Villa Fraulo isn’t shy about showing off its medieval roots. 

The Hotel Villa Guiseppina is a country hotel with views straight across the valley to Ravello. You’ll catch the best vistas from the panoramic pool. 

The Masseria Montelauro is rural living done right. The 19th-century whitewashed farmhouse lays out a swimming pool, garden restaurant and mini spa on the outskirts of Otranto. 

Trulli Soave is your chance to stay in a traditional trulli house. Round rooms, archways and conical roofs are the theme – as well as little extras like al fresco hot tubs and rose gardens with hammocks.  

Ancient Greek temples overlook the five-star Villa Athena. In fact, this 17th-century hotel lays out its own private path leading through the ancient olive groves to a UNESCO-listed archaeological park. 

A one-time Benedictine abbey, the Relais Santa Anastasia has all the markers of a Relais & Chateaux hotel – including a gourmet Sicilian restaurant. 

Agriturismo Il Granaio pairs a luxury finish with spades of Sicilian charm. The rural surroundings inspire the farmhouse restaurant, which sources ingredients from the fields and gardens. 

San Giorgio Palace carves out a spot on the rocky hillside of Ragusa. A tunnel leads you to reception, rooms come with country views, plus it’s only a few minutes’ walk from Piazza Duomo. 

Ocean and vineyard views wrap the Capofaro Malvasia & Resort. You can even have a go at harvesting the local Malvasia grapes – or just sit back with a glass of the good stuff. 

Baglio La Porta deftly whisks together the old and the new. Golden stonework and wood-beamed ceilings pair up with a glass-wrapped restaurant with panoramic sea views. 

The Algila Ortigia Charme Hotel plants itself right on Mastra Rua, in the centre of ancient Ortigia. It’s elegant, too, with rooms and a restaurant filling out a richly restored townhouse. 

The 17th-century Villa Don Camillo burrows amongst the fruit orchards just outside Sorrento. Cooking lessons and limoncello-making classes get you right under the skin of the region. 

Clean lines and sharply dressed rooms make the Villa Fiorella Art Hotel a modern pick. And the views speak for themselves – pull up a lounge chair on the bar terrace for views over the Sorrento coast. 

The Sextantio le Grotte della Civita converts ancient sassi cave dwellings into 18 luxury rooms. Archaic features like wobbly stone floors and hand-woven bedcovers add to the atmosphere. 

The Hotel Le Renaie is a family-run hotel in the Chianti countryside. The nearby village peers out and up to the famous towers of hilltop San Gimignano.  

Fancy staying in a 16th-century Tuscan farmhouse? Il Borgo di Montereggi and Il Casale have been transformed into a collection of holiday apartments with plenty of original features.  

The terracotta-topped Zampugna Apartments balance between Montepulciano and Pienza, in a sweep of countryside that’s a poster child for rural Tuscan life.  

Giuseppe Moschi and his family look after the Casa Vacanze Le Cellole – a lovingly restored Tuscan farmhouse with vineyard views and a pool. 

The pilgrimage city of Assisi is practically within grabbing distance of the Country House Tre Esse. Sip a glass of Umbrian red at the bar or check out the country views from the pool. 

The family-owned Hotel Villa Pambuffetti has spades of old-school Italian charm. Expect cypress-shaded gardens and a dining room serving local Umbrian cuisine. 

The Relais Villa Monte Solare Wellness & Beauty has won a place on the prestigious ‘Small Luxury Hotels of the World’ list. Stay in the main villa or the charm-packed 17th-century outhouses. 

Italian herb gardens and vineyards wrap around the Locanda La Raia – a country mansion with just 12 rooms and centuries of history.