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Luxury villas, boutique Simpson Hotels and unforgettable holidays

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Luxury boutique hotels in Italy

Offering a standard of hospitality that’s second to none, our luxury hotels in Italy have earned their place amongst our carefully chosen collection of Simpson Hotels. Thoughtfully and stylishly finished, they give our guests access to the many pleasures that a holiday in this beautiful country can bring.

And a boutique hotel comes with many advantages, not least the personalised care and attention our guests receive from the hotel owners. Their passion for customer service and extensive local knowledge will help make your luxury hotel holiday the best it can be.

The many pleasures of a hotel holiday in Italy

In a country that prides itself on its wine and makes every mealtime a celebration of fresh, local produce, there’s much to savour on the local menus, alongside breathtakingly beautiful countryside and a myriad of hilltop towns and villages, all waiting to be explored. If you can tear yourself away from your luxury hotel pool.

Handpicked hotels with plenty to do

We chose our boutique hotels because they have something special about them – and that unique quality is created, in part, by the people who own them. However, it’s also about their location at the heart of Italy’s glorious landscapes giving you access to walking trails, horse riding, wine tasting and the rich history and culture in the form of art galleries, chic boutiques, local arts and crafts, museums, majestic cathedrals and peaceful churches. It’s what makes our luxury hotels in Italy the magical holiday destinations that they truly are.

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Masseria Amastuola

Puglia, Italy

Hotel | Bedroom 1 | Sleeps 2

  • Chic contemporary Partner Hotel
  • Vineyard setting
  • Wine tours and tastings on site
  • Excellent restaurant

Prices are based on 2 sharing for 7 nights on Saturday 22 October 2022

Accommodation Only

  • Suite & breakfast

Prices
from

$670pp Total price $1,339
View details
Reserve now for 2023 with a fully refundable deposit of $650

Use our Advanced Registration service to secure your 2023 holiday with a deposit of $650, fully refundable when prices are published

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Masseria Garrappa

Puglia, Italy

Hotel | Bedroom 1 | Sleeps 2

  • Charming Partner Hotel
  • Cookery courses available daily
  • Excellent restaurant
  • Short stays available

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

Accommodation Only

  • Suite & breakfast

Prices
from

$715pp Total price $1,430
View details
Reserve now for 2023 with a fully refundable deposit of $650

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Masseria Mongiò dell Elefante

Puglia, Italy

Hotel | Bedroom 1 | Sleeps 1-4

  • Stylishly restored Masseria in southern Puglia
  • Elegant restaurant and bar
  • Complimentary welcome dinner
  • Beautiful gardens and grounds

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

Accommodation Only

  • Suite & breakfast

Prices
from

$748pp Total price $1,495
View details
Reserve now for 2023 with a fully refundable deposit of $650

Use our Advanced Registration service to secure your 2023 holiday with a deposit of $650, fully refundable when prices are published

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Leonardo Trulli Resort

Puglia, Italy

Hotel | Bedrooms 1-2 | Sleeps 2-3

  • Converted trulli and masseria
  • Beautifully tended gardens
  • In the heart of the fashionable Valle d’Itria
  • Locorotondo 10-minute drive

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

Accommodation Only

  • Room & breakfast

Prices
from

$813pp Total price $1,625
View details
Reserve now for 2023 with a fully refundable deposit of $650

Use our Advanced Registration service to secure your 2023 holiday with a deposit of $650, fully refundable when prices are published

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Masseria Le Torri

Puglia, Italy

Hotel | Bedroom 1 | Sleeps 2

  • Elegant Partner Hotel
  • 9 stylish suites
  • One complimentary dinner for stays of 3 nights or more
  • Polignano and beach 15-minute drive

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

Accommodation Only

  • Suite & breakfast

Prices
from

$829pp Total price $1,657
View details
Reserve now for 2023 with a fully refundable deposit of $650

Use our Advanced Registration service to secure your 2023 holiday with a deposit of $650, fully refundable when prices are published

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Masseria Francescani

Puglia, Italy

Hotel | Bedroom 1 | Sleeps 2-3

  • Elegant Masseria in Southern Puglia
  • Beautifully renovated and elegantly appointed
  • Delightful garden and pool terrace
  • Exclusive restaurant

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

Accommodation Only

  • Suite & breakfast

Prices
from

$1,011pp Total price $2,022
View details
Reserve now for 2023 with a fully refundable deposit of $650

Use our Advanced Registration service to secure your 2023 holiday with a deposit of $650, fully refundable when prices are published

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Il Sogno delle Benedettine

Puglia, Italy

Hotel | Bedroom 1 | Sleeps 2

  • Partner Hotel in the historic centre of Ostuni
  • Beautifully renovated traditional building
  • Sophisticated interiors and stylish decor
  • Pretty courtyard garden

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

Accommodation Only

  • Room & breakfast

Prices
from

$1,055pp Total price $2,109
View details
Reserve now for 2023 with a fully refundable deposit of $650

Use our Advanced Registration service to secure your 2023 holiday with a deposit of $650, fully refundable when prices are published

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Reserve Now

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Reviews

Simpson Travel in the media

  • ‘[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

  • ‘The Simpson Travel check-in at Heathrow’s Terminal 5 was seamless.’ Author: Family Traveller, Katy Hill

  • ‘Where Simpson [Exclusive] really excels is in its first-hand knowledge of properties and destinations’ Author: House & Garden

  • ‘Simpson [Exclusive] delivers holidays that combine sunshine, five-star luxury and friendly service’ Author: House & Garden

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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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Menu

  • Destinations

    Destinations

    France

    France

    • Provence
    • The Dordogne & South West
    • Vendée
    • Aquitaine Coast
    • Ile de Ré

    Mallorca

    Mallorca

    • Fornalutx & Sóller
    • Pollença & Puerto Pollença

    Greece

    Greece

    • Corfu
    • Crete
    • Ithaca
    • Kefalonia
    • Lefkada
    • Meganissi
    • Paxos
    • Sivota
    • Zakynthos

    Turkey

    Turkey

    • Akyaka
    • Bozburun Peninsula
    • Islamlar & Uzumlu
    • Kalkan
    • Kaş

    Italy

    Italy

    • Tuscany
    • Umbria
    • Puglia

    Corsica

    Corsica

    • Calvi & The Balagne
    • Porto Vecchio & Bonifacio
    • The Valinco
  • Villas

    Villas

    • Villas with childcare
    • Luxury villas
    • Off the beaten track villas
    • Car-free villas
    • Large group villas
    • Villas together
    • Romantic villas for two
    • Family Favourite villas
    • Teen-friendly villas
    • Beachfront villas
    • Villas with heated pools
    • Villas near the beach
    • Villas near a restaurant

    Back

  • Hotels

    Hotels

    • Simpson Hotels
    • Partner hotels
    • Family hotels
    • Beachfront hotels
    • Adult-only hotels
    • Romantic hotels for two
    • Hotels with childcare
    • Car-free hotels

    Back

  • Holiday inspiration

    Holiday inspiration

    Holiday Types

    Holiday Types

    • Couples holidays
    • Beach holidays
    • Large group holidays
    • Car-free holidays
    • Twin Centre holidays
    • 10-night holidays
    • Countryside holidays
    • Honeymoons
    • Babymoons
    • Special Interest Holidays
    • Experiences and Activities

    Family Holidays

    Family Holidays

    • Holidays with childcare
    • Easter holidays
    • Half-term holidays
    • Multi-gen holidays

    Collections

    Collections

    • Simpson Exclusive
    • Simpson Secrets
    • Simpson Hotels
    • Simply Simpson
    • Simpson Kids
    • Simpson Bespoke

    Our Blog

    Our Blog

    • Where to go
    • What to do
    • What's new
    • Views and reviews
    • Family travel
    • 2022 holidays
    • Give the gift of travel
  • About us

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    • Why Simpson Travel?
    • Travel arrangements
    • Advance Registration
    • Our heritage
    • Awards
    • Reviews
    • Loyalty Club
    • Our Destination Specialists
    • Giving back
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    Back

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You'll also be able to enter into our new quarterly competition, with the chance to win a holiday

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