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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 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 16 October 2021

Accommodation Only

  • Suite & breakfast

Prices
from

$555pp Total price $1,110
View details
Go to property page

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 2 October 2021

Accommodation Only

  • Room & breakfast

Prices
from

$817pp Total price $1,634
View details
Go to property page

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 16 October 2021

Accommodation Only

  • Suite & breakfast

Prices
from

$828pp Total price $1,655
View details
Go to property page

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 3 July 2021

Accommodation Only

  • Suite & breakfast

Prices
from

$882pp Total price $1,764
View details

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Reviews

Simpson Travel in the press

  • ‘[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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Holiday ideas

  • Holidays in Corsica
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  • Villas in Italy
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  • Villas in Turkey

Travel advice from the Foreign Office

For up-to-date advice and information on travelling abroad, including passports, visas and health and safety, please visit the Foreign Commonwealth & Development Office website or call 020 7008 1500.

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

    Destinations

    France

    France

    • Côte d'Azur
    • Provence
    • The Dordogne & South West
    • Vendée
    • Aquitaine Coast
    • Ile de Ré

    Mallorca

    Mallorca

    • 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
    • Central Corsica
    • Porto Vecchio & Bonifacio
    • The Valinco
    • West Coast
  • 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 types

    Holiday types

    • 2021 Holidays
    • Couples holidays
    • Easter holidays
    • Half-term holidays
    • Holidays with childcare
    • Multi-gen holidays
    • Large group holidays
    • Solo Travel
    • Beach holidays
    • Twin centre holidays
    • Countryside holidays
    • Honeymoons
    • Babymoons
    • Experiences and Activities

    Back

  • Collections

    Collections

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

    Back

  • About us

    About us

    • Simpson Safe
    • Why Simpson Travel?
    • Travel arrangements
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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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