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Holidays in historic towns and villages in Italy

For a holiday with the rich heritage of times gone by, you’ll find a wealth of interesting buildings and artefacts in the historical towns and villages of Italy. Even better, these engrossing locations are never too far away from our luxury villas in the Tuscany and Umbria regions.

Asked to compile a list of Italy’s most notable historical locations, many of us would include Rome, Florence, Pisa, Siena and Venice. While these cities can certainly help to bring history to life when you visit, there’s a multitude of smaller towns and villages across Italy that are also worth seeing.

For example, in Tuscany alone, Arezzo has an impressive Duomo and a tradition of gold-smithery that makes it one of the richest towns in the region. Also set within the beautiful Tuscan landscape, the hill-topping Cortona dates back to Etruscan times and was chosen by St Francis of Assisi as the site of his first monastery.

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Showing search results for 'Italy'. (15 results found)

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Tuscany, Italy

Accom only prices from £1,300 Help

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Villa | 3 bedrooms | Sleeps 6

  • Stylish and comfortable barn conversion
  • Extensive garden with small lake
  • Cooking classes available

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Tuscany, Italy

Accom only prices from £650 Help

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Apartment | 2 bedrooms | Sleeps 4

  • Beautiful converted apartment
  • 17th-century building
  • Private terrace with delightful views

La Madonnina

United by warm welcomes, excellent service and attention to detail, our handpicked Simpson Hotels include our unique Adult Only Collection and, for families, comfortable, versatile accommodation in locations well suited to guests of all ages.
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Tuscany, Italy

Accom only prices from £660 Help

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Hotel | 1-2 bedrooms | Sleeps 2-4

  • Delightfully small Simpson hotel
  • Stunning views
  • Beautiful gardens

Tuscany, Italy

Accom only prices from £750 Help

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Villa | 3 bedrooms | Sleeps 6

  • Comfortable refurbished villa
  • Set in an extensive manicured garden
  • Ideal for two families travelling together

Tuscany, Italy

Accom only prices from £750 Help

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Villa | 1 bedroom | Sleeps 2

  • Charming property for two
  • Comfortable and spacious
  • Stunning views across rolling hills

Tuscany, Italy

Accom only prices from £800 Help

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Apartment | 2 bedrooms | Sleeps 3

  • Contemporary and comfortable apartment
  • Ideally located to explore Chianti
  • Magnificent swimming pool

Tuscany, Italy

Accom only prices from £1,110 Help

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Villa | 1 bedroom | Sleeps 2

  • Charming bijou Chianti villa
  • 'Room with a view'
  • A romantic interlude

Tuscany, Italy

Accom only prices from £1,200 Help

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Villa | 5 bedrooms | Sleeps 10

  • Tranquil, spacious retreat
  • Stunning panoramic views
  • Comfortable interiors

Umbria, Italy

Accom only prices from £1,300 Help

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Villa | 5 bedrooms | Sleeps 6-9

  • Calming and welcoming country house
  • Spacious and comfortable
  • Captivating views

Tuscany, Italy

Accom only prices from £2,695 Help

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Villa | 7 bedrooms | Sleeps 13

  • Exceptional manor house
  • Spacious and comfortable
  • Set in the heart of Chianti