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Rural retreats in Italy

For the ultimate ‘get away from it all’ countryside holiday, Italy’s abundance of unspoilt landscapes and picturesque villages offer the discerning traveller a taste of times gone – and an irresistible choice of rural retreats. Allow Simpson Travel to be your guide to the rolling hills and valleys of Tuscany and Umbria.

Of course, Italy’s fertile interior has more than scenery to savour: you’ll find freshly-grown local produce in the country markets across Tuscany, as well as numerous seasonal festivals celebrating everything from Chianti’s fine wines to steaks and chestnuts. It’s a taste of authentic Italy that you can take back to your cosy rural retreat for a meal bursting with traditional flavours

Umbria, sometimes known as ‘the green heart of Italy‘, offers similar delights. Not only is the countryside a feast for the eyes, it rewards you more literally with traditional delicacies such as truffles and cured meats, as well as its own collection of world-famous wines.

And after a day of exploration, your Simpson Travel luxury villa will be waiting for you: the perfect countryside retreat. Hand-picked for the quality of its finish and furnishings, and its tranquillity, your rural hideaway gives you the space to relax and re-charge, close enough to shops and restaurants to make life easy, secluded enough to give you the gift of perfect peace and privacy.

Then you’ll be ready to emerge again, all set for another adventure in the beautiful Italian countryside.

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La Canonica di Cortine Cottages

Tuscany, Italy

Villa | Bedrooms 2 | Sleeps 4

  • Five unique two-bedroom cottages
  • Part of a beautifully restored historic hamlet
  • Informal and friendly
  • Delightful views of Chianti countryside

Prices are based on 2 sharing for 7 nights on Saturday 28 May 2022

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  • Cottage

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$878pp Total price $1,755
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Casa al Colle

Tuscany, Italy

Villa | Bedrooms 5 | Sleeps 10

  • Elevated, spacious retreat
  • Stunning panoramic views
  • Comfortable interiors
  • Simpson family extras available

Prices are based on 2 sharing for 7 nights on Saturday 8 October 2022

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  • Villa

Prices
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$972pp Total price $1,944
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Villa Donatella

Umbria, Italy

Villa | Bedrooms 5 | Sleeps 6-9

  • Calming and welcoming country house
  • Spacious and comfortable
  • Captivating views
  • Excellent location to explore Umbria

Prices are based on 2 sharing for 7 nights on Saturday 15 October 2022

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  • Villa

Prices
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$1,374pp Total price $2,747
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Trulli Gianpaolo

Puglia, Italy

Villa | Bedrooms 3 | Sleeps 5

  • Enchanting trulli house
  • Val d’Itria location
  • Picturesque garden
  • Private pool

Prices are based on 2 sharing for 7 nights on Saturday 8 October 2022

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  • Villa

Prices
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$1,398pp Total price $2,795
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Villa Mille Desideri

Tuscany, Italy

Villa | Bedrooms 6 | Sleeps 11

  • Beautifully positioned villa
  • Breathtaking views
  • Comfortable and welcoming
  • Simpson family extras available

Prices are based on 2 sharing for 7 nights on Saturday 15 October 2022

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  • Villa

Prices
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$1,610pp Total price $3,219
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Colto dei Pallanti

Tuscany, Italy

Villa | Bedrooms 3 | Sleeps 6

  • Beautifully restored farm house
  • Stunning panoramic views
  • Heated pool
  • Simpson family extras available

Prices are based on 2 sharing for 7 nights on Saturday 8 October 2022

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  • Villa

Prices
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$1,613pp Total price $3,226
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Reserve now for 2023 with a fully refundable deposit of $650

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Villa Aia

Puglia, Italy

Villa | Bedrooms 4 | Sleeps 8

  • Stylish contemporary villa
  • Beautiful countryside views
  • Peaceful and secluded
  • Media room

Prices are based on 2 sharing for 7 nights on Saturday 15 October 2022

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  • Villa

Prices
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$1,681pp Total price $3,362
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Reserve now for 2023 with a fully refundable deposit of $650

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Masseria Borgo San Benedetto

Puglia, Italy

Villa | Bedrooms 4 | Sleeps 8

  • Imposing 18th century masseria
  • Spacious elegant interiors
  • Walled garden with pool
  • 5-minute drive to Conversano

Prices are based on 2 sharing for 7 nights on Saturday 15 October 2022

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  • Villa

Prices
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$2,048pp Total price $4,095
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Reserve now for 2023 with a fully refundable deposit of $650

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Villa Rosa

Tuscany, Italy

Villa | Bedrooms 4 | Sleeps 8

  • Historic 19th century building
  • Extensive private grounds
  • 16-metre swimming pool
  • Tower lounge with beautiful views

Prices are based on 2 sharing for 7 nights on Saturday 8 October 2022

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  • Villa

Prices
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$2,210pp Total price $4,420
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Reserve now for 2023 with a fully refundable deposit of $650

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Villa Vita

Umbria, Italy

Villa | Bedrooms 3 | Sleeps 2-6

  • Stunning contemporary villa
  • State-of-the-art design
  • Heated swimming pool and sauna
  • Exceptional countryside views

Prices are based on 2 sharing for 7 nights on Saturday 24 September 2022

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  • Villa

Prices
from

$2,340pp Total price $4,680
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  • ‘[Simpson Travel] specialise in the sort of magical, unspoilt destinations my family loves’ Author: The Telegraph

  • ‘So how did we find the near-perfection that was Villa Cabanellas in Mallorca? The first step was to approach… Simpson Travel… we needed expertise, not just blinding choice.’ Author: Sunday Times Travel Magazine, The Villas Handbook

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Travel advice

For up-to-date advice and information on travel from the UK, including passports, visas and health and safety, please visit the Foreign Commonwealth & Development Office website or call 020 7008 1500. For travel from countries outside the UK, please visit your corresponding government website.

The air holidays and flights shown are ATOL protected by the Civil Aviation Authority. Our ATOL number is ATOL 5858. ATOL protection extends primarily to customers who book and pay in the United Kingdom. Find out more about ATOL. Simpson Travel is the trading name of Far & Wide Ltd.

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  • Destinations

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    • Provence
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    • Romantic villas for two
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    Back

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