La Madonnina

Tuscany, Italy

Part of theSimpson Hotels collection

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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  • Delightfully small Simpson Hotel
  • Stunning views
  • Two 2-bedroom suites, one cottage
  • Beautiful gardens
  • Local bar and grocery shop 10-minute stroll
  • Castiglion Fiorentino 10-minute drive
Book this much-loved Simpson Hotel as part of our Tuscan Wandering programme and we’ll treat you to a complimentary two-hour cookery lesson to discover the art of perfect pasta. Find out more about Tuscan Wandering.


At the end of the drive leading up to this charming Simpson Hotel is the small 17th-century shrine to ‘The Little Mary’ who gave the house its name. As recently as the late 1980s, visitors came to make offerings there, but now, in this beautiful Tuscan landscape of vineyards, olive groves and the Val di Chio, we suggest a different kind of pilgrimage is in order. Whether you’re on a quest for relaxation for two or a family retreat in the school holidays, this is a destination that restores calm and invites exploration in equal measures. With two well-designed two-bedroom suites (Gli Avi and La Nonna) which include kitchens, this small, peaceful hotel accommodates families and couples alike, although for those seeking a romantic retreat, it offers La Capannina, a sweet little studio set apart from the main building with its own al fresco dining area. Each is decorated in typical country style with a light touch – exposed beams and brickwork offset by white painted walls – very much in keeping with the relaxed atmosphere and homely feel created by the owners Maria and Rinaldo.

The property has been in the family for generations and, in 2016, working closely with the Simpson Travel team, the couple transformed it to reflect the style and ambience of our own unique Simpson Hotels, with Rinaldo’s signature sculptures dotted around the garden and large stone fireplaces. We couldn’t be happier with the results.

Although Gli Avi is the larger of the two suites with a private terrace to match, the stunning views are for everyone, as is the shared swimming pool and the lovingly tended gardens where you can breathe out stress and just relax.

As with all our Simpson Hotels, breakfast is provided, but Maria’s generosity of spirit and culinary flair extends to more than a delicious start to the day. A complimentary light welcome dinner is also included (excluding Tuscan Wandering bookings), and you can pre-order other meals, created from fresh, seasonal produce, and pay for them locally – or even take a cookery course. She’s also a mine of local information and is never far away if you’re looking for inspiration or a well-informed and passionate local perspective on the region’s very best attractions.

The local area

The nearest local bar and a basic grocery store are just a 600m stroll away. For everything else, there’s Castiglion Fiorentino, a ten-minute drive away or 6km along a footpath and cycle track. This impressive Renaissance town rises above the Valdichiana Plain and has banks, shops and chemists, as well as atmospheric bars, traditional squares, open-air restaurants and culture aplenty – the old Gothic church of San Francesco and the Madonna della Consolazione temple are worth a visit. The town also hosts a number of lively festivals, including an eight-day medieval festival at the end of May/beginning of June, complete with traditional food, costumes, parades and fireworks.

For walkers, this region is flanked on one side by the Pratomagno Mountains and on the other by the attractive Alpe di Catenia and, being near the Umbria-Tuscany border, you’re well placed to explore both regions. 

For day trips, Florence is easily accessible by train and Cortona, Lake Trasimeno and Perugia are also within easy reach.


Accommodation

Layout

  • Two 2-bedroom suites (sleeps 2-4)
  • Studio cottage (sleeps 2)

Gli Avi

  • 2-bedroom suite
  • Open-plan sitting/dining/kitchen area with open fireplace
  • Kitchen includes hob, gas oven, fridge; French door leads to large terrace for dining al fresco
  • Stairs lead up to double bedroom
  • Twin bedroom (can be configured into a double if required)
  • Shower room

La Nonna

  • 2-bedroom suite
  • Open-plan sitting/dining/kitchen area with open fire place
  • Kitchen includes hob, gas oven, fridge; French door opens to small terrace
  • Stairs lead up to double bedroom
  • Twin bedroom (can be configured into a double if required)
  • Shower room

La Capannina

  • Studio cottage
  • Double bedroom with en-suite shower room
  • Outdoor seating/dining area

General

  • Air-conditioned bedrooms
  • Complimentary WiFi
  • Breakfast included
  • Complimentary light welcome dinner (excluding Tuscan Wandering bookings)
  • Tea and coffee making facilities
  • Upgrade to half-board available (payable locally – pre-booking recommended)
  • Menu
  • Hairdryer
  • Laundry room (first wash is complimentary, thereafter payable locally)
  • Pool towels provided
  • Shared swimming pool 6m x 12m (depth 1.40m throughout)
  • In Italy, a daily tourist tax applies for the first week of your stay only, which means that an average of €1.50 per person (12+ years) may be charged. This should be paid in cash to the owner during your stay.
  • Due to the cooler temperatures, the swimming pool will be closed from 30 September until the end of the season

WiFi

  • All properties with WiFi are able to support basic functionality such as web browsing and checking emails*

* We aim to offer an uninterrupted service but sometimes due to factors beyond our control reliability can be affected.

Access times

  • Check in time – 4-8pm
  • Check out time – 10am

Location

  • Localitá Santa Cristina (bar and grocery shop) 10min walk
  • Castiglion Fiorentino (shops/restaurants) 10min drive
  • Cortona 30min drive
  • Arezzo 40min drive
  • Siena 1hr 10min drive
  • Florence 1hr 30min drive
  • Pisa airport 2hr 15min drive
  • Rome Fiumicino airport 2hr 30min drive

Flights

Below are the flight options available, including the most convenient airports in Italy to help you reach your destination as quickly and easily as possible. Please be aware that flight supplements may apply, subject to availability. 

Pisa

Departure airport Airline Flight days Seasonality
London Heathrow British Airways Saturday All season
London Gatwick easyJet Saturday All season
London Gatwick British Airways Saturday All season
London Stansted Ryanair Saturday All season
Luton Airport easyJet Saturday All season
Manchester Jet2 Saturday All season
Manchester easyJet Saturday All season
Bristol easyJet Saturday All season

Florence

Departure airport Airline Flight days Seasonality
London City British Airways Saturday All season

Rome

Departure airport Airline Flight days Seasonality
London Heathrow British Airways Saturday All season
London Heathrow Alitalia Saturday All season
London Gatwick British Airways Saturday All season
London Gatwick easyJet Saturday All season
London Gatwick Vueling Saturday All season
Manchester Jet2 Saturday All season
Birmingham Monarch Saturday All season
Bristol easyJet Saturday All season

Car hire

Car options

Based on the number of people travelling, the following hire car(s) are included in the package price of your holiday:

  • 2 guests – 1 group B, Fiat Panda or similar*
  • 3 guests – 1 group C, Lancia Ypsilon or similar*
  • 4 guests – 1 group D, Volkswagen Golf or similar*

* All our cars include comprehensive insurance with zero excess. For this particular destination, the undercarriage is not included in the cover.

Car specifications

Group B – 1.2 litre engine, 2 small suitcases*

Group C – 1.2 litre engine, 2 medium suitcases*

Group D – 1.6 litre engine, 3 large suitcases*

The following cars are available as alternatives on request (supplements apply). Please call our travel specialists for details.

Group F – Volkswagen Golf AUT or similar, 1.6 litre engine, 3 large suitcases*

* Suitcase sizes are based on a large suitcase being approximately 75cm x 41cm x 31cm, a medium suitcase of approximately 65cm x 46cm x 29cm and a small suitcase of 55cm x 40cm x 20cm.

Customer feedback

La Madonnina is a perfect venue for a relaxed time away. Maria and Ronaldo are excellent hosts and the style of their relationship with their guests is most welcoming and warm. The surroundings are picturesque and delightful and within reach of many of the best cultural sites in Italy.
Barry & Pat – September 2018

La Madonnina was a lovely, peaceful place to stay. Maria was an excellent, friendly host and couldn't do enough for us. It's a quiet location which is wonderful for relaxing, but Florence, Arezzo and Sienna are within easy reach. There are good restaurants in Cortona and Castiglion.
Mr Spence – La Capannina – August 2018

La Madonnina is a perfectly lovely property which we would visit again and again.
Diane – La Capannina – August 2018

Four of us had a relaxing, hot and sunny week at La Madonnina. Gli Avi is a comfortable base with a welcoming and very friendly hostess (and characterful puppy, Eva). Breakfasts were open air and tasty and the two dinners that Maria cooked and served were excellent. The views from the terrace are magnificent and the pool inviting. The area is very attractive. Just perfect!
R Shaw – August 2018

We spent a lovely week at La Madonnina. Castiglion Fiorentino is a great town with really nice places to eat. If you don’t fancy going out, Maria cooks a fabulous meal and there is loads to eat. Maria is a wonderful host and nothing is too much trouble.
The Holder Family – Gli Avi – July 2018

Lovely region, lovely tours, fabulous property, really enjoyed conversing in broken Italian/English with Maria and Ronaldo. It’s a gem of a spot and we won’t forget it. Well done Maria. Well done Simpson Travel.
John, Skye & Kara– La Nona – July 2018

We had an amazing time, thank you so much. Maria’s cooking was fabulous and was a real treat to sit on the terrace enjoying amazing food. We loved the area and enjoyed re-visiting many places that we have visited before.
Karen & Gary – La Nona – July 2018

We had a wonderful stay at La Madonnina and Maria was a fantastic host. The breakfast view will live with us forever. We really enjoyed visiting Cortona and our trip to the lake.
Janine & Martin – La Capannina – July 2018

What a wonderful place to relax and enjoy the amazing views. Maria cooked us two fabulous meals and we were joined by the others also staying there. Many thanks to Maria and Rinaldo for making our stay at La Madonnina so special.
Rowena, Martin & Gaby – Gli Avi – July 2018

We book with Simpson Travel as we know what we will get – out of the ordinary in every way, great locations, fabulous hosts and kindred spirits. Both our selected properties in Tuscany, La Madonnina and La Canonica di Cortine, had so much to recommend them whilst being totally different – a great combination.
Martin Sims – Gli Avi – July 2018

We thoroughly enjoyed our stay at La Madonnina. Our host, Maria, was friendly, helpful and went out of her way to make us feel welcome. The breakfasts each morning were fresh and plentiful and our welcome evening meal was so delicious that we had another one on our last evening! All three accommodation options were beautifully presented and well appointed. We loved our holiday.
Mrs Hatton – La Capannina – July 2018

We had the most wonderful time. One week at La Madonnina was not enough to explore such a beautiful location – the only option is to return! One of the highlights for us was learning to make pasta with Maria. We can’t recommend it enough. She is a superb cook and we enjoyed one of her meals on our last night. We were so sad to leave. We loved Cortona, Arezzo and Florence. Travelling by train was easy…. Thank you very much Maria and Ronaldo.
Vikki & John – La Capannina – June 2018

Maria has been a wonderful host at La Madonnina, and despite our limited Italian and Maria’s limited English, we managed to have lots of happy conversations together. Maria welcomed us into her home to watch England play in the World Cup and also prepared a delicious meal on our first evening. The local area is stunning and with lots of interesting places to visit – Cortona and Arezzo are both within easy reach.
Mike & Geraldine – Gli Avi – July 2018

One of our best holidays in Italy – the perfect setting, good weather and such a warm and generous welcome from Maria, who could not have been more helpful. We did not need to venture very far (though Cortona is delightful), and we spent most of our time painting and pottering locally. Maria and Rinaldo are such good hosts. We will miss La Madonnina.
Su & Jon – Gli Avi – June 2018

We had a great time at La Madonnina. Maria and Rinaldo could not have been more hospitable and we came away feeling that we had experienced a slice of authentic Italian life. If you get the chance to make pasta with Maria it really is an opportunity not to be missed – we thoroughly enjoyed it. I can also recommend sampling her home cooking – delicious. It’s in a central location from where you can explore the beautiful region of Tuscany. I can recommend taking the train to Arezzo and Florence, which we found very straightforward. There is much to do and see within easy reach and we particularly enjoyed Cortona which is only 20 minutes or so by car.
Mr & Mrs Fletcher – La Capannina – July 2018

Tranquillity is what we look for on a holiday and La Madonnina provided this and more. It was wonderful to see the roses at their very best. We were two couples staying in La Nonna and we loved our little cottage, especially the cosy terrace. Our day trips included Cortona and Arezzo. Ask Maria for some of their olive oil and the neighbour’s red wine!
Rosie, Jozef, Jan & Aad – June 2018

La Madonnina has been a wonderful place to stay and experience the beauty of Tuscany. It has been made even more relaxing by the stunning surroundings, the delicious food, the local wine and the generosity of Maria. Cortona, Castiglion Fiorentino, Montepulciano, Florence and Arezzo were beautiful places to visit and the wild flowers at this time were wonderful.
Lucy & Pete – Gli Avi – May 2018

This is my 3rd or 4th holiday with Simpson Travel and I cannot fault them. It is so nice to deal with a company that speaks to you regularly and sorts out any problems and is so knowledgeable about their properties. I run my own business and if my staff were half as friendly and attentive I would be very happy.
Mr Beese – May 2018

This has been a wonderful place to stay and experience the beauty of Tuscany. It has been made even more relaxing by the stunning surroundings, the delicious (squisito) food, local wine and Maria’s generosity. Cortona, Castiglion Fiorentino, Montepulciano, Florence and Arezzo have been beautiful places to visit and the wild flowers at this time have been wonderful. Thank you.
Mr and Mrs C – May 2018

We’ve had an amazing week at La Madonnina. Trips to Siena, Rome and Cortona, winemaking at the vineyard down the road and a lot of relaxing by the pool. Maria was incredibly helpful and hospitable and all these things combined made it a memorable time.
Mark Wright & Kay Steven – La Nonna – May 2018

What a wonderful place, so beautiful and peaceful. The apartment is lovely and the beds so comfortable. Maria has been so kind and the breakfasts have been amazing. She also brought us some treats in the evening! We drove to Cortona which was fascinating and took the train to Arezzo. Unfortunately we did not stay long enough to do a few more trips, but at least we had a very restful time. We will remember the stunning views.
Pat & Brian D'Olier – La Nonna – May 2018

 

Just like everyone else that has stayed here, we have had an amazing week! Maria and Ronaldo have looked after us so well. Maria’s cooking is amazing and we managed to get the rest we so desperately needed.
Penny & Mick – Gli Avi – May 2018

Thank you Maria and Rinaldo for looking after us so well. We had a lovely time.
Roger and Jane – September 2017

We've had a wonderful stay here. Maria has been a fabulous host. Breakfast has been delicious and Maria was flexible on times when we wanted an early start to catch the train to Florence. We visited Cortona and Lake Trasimeno, both easily reachable by car. Siena is just over an hour by car and is a fabulous city to visit and explore. This is our last evening in this very tranquil and relaxing place. Maria fetched us pizza to eat on our balcony – perfect with a bottle of local red wine! Thanks for an excellent holiday.
Dave & Linda Hendrey – June 2017

We've had a brilliant time here at La Madonnina. Beautiful place and wonderful hosts. Nothing is too much for Maria – a truly lovely person!
John and Sara Coghler – May 2017

Thank you very, very much for welcoming us at La Madonnina! We enjoyed the beautiful views, the pool and visiting the nearby villages. Maria is a wonderful host, always ready to help or play with the children. Thank you!
Stefan, Maria, Abel & Pierre – August 2017

Thank you for a truly relaxing stay at La Madonnina. It has been a perfect setting to enjoy the wonderful breakfasts, lazy lunches and hours of fun in the pool. We loved our week here in Tuscany. Thank you Maria and Rinaldo for welcoming us into your home.
Simon, Lesley, Phoebe & Ted – August 2017

We have spent two very happy weeks at La Madonnina in the care of Maria and Rinaldo. We loved the area – sitting on our terrace looking at the views is such a splendid way to pass time! We have been to see lots of wonderful places including Siena, Montepulciano, Montalcino, Cortona, Arezzo, not forgetting our local special town of Castiglion Fiorentino. We have eaten and drunk well – the Tuscan food and wine is delicious. Oh some more time here!
Jan and Norman – September 2017

We’ve had a wonderful first family holiday here with our baby. Maria is a marvel – do sample her delicious cooking and see how she makes pasta. Remember to visit Cortona – we had a lovely lunch at Logetta (on the terrace overlooking the square). La Madonnina is obviously in a beautiful serving, but Maria’s hospitality and warmth made it extra special. We would love to come back.
Rebecca, Ross and Edward – September 2017

Very much enjoyed staying at La Madonnina and thank you to Maria for her hospitality throughout. I can now make pasta like an Italian! So many lovely places but loved Arezzo and natural spring spa at Rapolano and the Chianti Run.
Andrew and Lorraine – September 2017

Thank you so much Maria for making our stay so welcoming. We had a lovely week with fantastic weather and enjoyed seeing Arezzo and Cortona.
The Crowns – September 2017

A delightful week at La Madonnina! Maria is the perfect hostess and made us feel instantly at home in our comfortable apartment. We greatly appreciated her cooking after a day's sightseeing in this beautiful part of Tuscany. The breakfasts on the terrace gave us the opportunity to meet our fellow guests and compare notes on our excursions.
The McClelland's – September 2017

Thank you so much for the welcome at La Madonnina! We have enjoyed a fantastic week here in Tuscany. Maria, Rinaldo and Jack have been amazing hosts and have made our stay so much better. It is a wonderful location to explore with Sienna and Florence so accessible by rail and car. This has been our first family holiday to Italy and we will definitely be back for more!
Colin, Alison, Cadi, Matthew & Nan – September 2017

We had a brilliant stay here, thank you so much for all the places you recommended. Thank you for making this such an enjoyable stay (especially Maria). The site was peaceful however it was only a short drive to a number of restaurants and activities. Thank you.
The Wolstenholme family – August 2017

What a wonderful place to stay! Maria and Rinaldo, you have been excellent hosts! Thank you so much! Siena really worth the drive and Cortona was one of the best towns we have visited in Italy! So gorgeous in the evening too. An absolute delight.
Lavina, Simon, Sam and Max – August 2017

We had a wonderful time at La Madonnina. Beautiful place and scenery. Maria and Rinaldo are amazing hosts,couldn't do enough for us as a family.
Mrs Colbert – August 2017

This is my third time in Italy and I loved it. Every night the view is amazing. I loved all the food and it was fun to play with Jack.
Issy, aged 9 – August 2017

We had a fabulous week at La Madonnina. Maria is a wonderful host and we enjoyed the lovely home-cooked meals on several occasions. La Nonna is extremely comfortable (especially the beds!) and the pool is delightful with fantastic views across the valley – not to mention lovely and cool as we have dodged the 40+ temperature this week. We enjoyed Assissi and Corbana particularly and the Tuscan countryside in general. Thank you Maria, Rinaldo and Jack for a lovely relaxing week.
Bronwen, Steve and Sam – August 2017

We have spent a wonderful two weeks here as a family of four – as we sit on the terrace on our last evening, having enjoyed yet another of Maria's fabulous home cooked meals. We are very sad to be leaving especially Maria, Rinaldo and Jack! This is such a special place and the hospitality offered by Maria is second to none – she treats you as family, welcoming you in her home and we have certainly felt adopted by her! La Madonnina is a great place in which to relax and retreat to after busy days spent exploring Tuscany. As other guests have suggested – the train is great – local, fairly priced, easy to use and free parking at the station, which makes it a good alternative to driving into the cities. In spite of the wide choice of restaurants, our favourite meals have certainly been cooked by Maria – truly wonderful! Thank you Maria and Rinaldo for a wonderful and holiday and making our first Italian family holiday so memorable.
Karen, Graham, Amelia & Olivia Potts – July 2017

Wonderful stay at La Madonnina. Maria was an amazing host. If you are lucky enough to have her home-cured prosciutto and salami you are in for a treat. Castiglion Fiorentino is a wonderful local town. We ate at Silla’s Bistro and Muzzicone – both very good especially the steak at Muzzicone. There is so much to see in Tuscany but don’t overlook Cortona and Arezzo (by train) as local trips.
Peter & Jo – July 2017

Just wanted to confirm what you described as a fabulous holiday location – Maria at la Madoninna is just fabulous. We wanted to share our delight of what we've experienced so far – we only arrived last night!! Fabulous location, amazing hospitable hosts – perfecto!
The Potts Family – July 2017

We had a lovely holiday at La Madonnina... The host was superb and the accommodation was a lovely rural Tuscan experience. Very peaceful and relaxing.
Audrey Riddle – July 2017

Maria at La Madonnina was really lovely. Very helpful and friendly.
Barbara Sedgwick – July 2017

We enjoyed our stay very much and the owner of the property (Maria) was extremely helpful and could not do enough to ensure our comfort. I have no criticism whatsoever and would not hesitate to go back.
Donald Heath – June 2017

Our choice of Italian properties is diverse, ranging from simple charm to genuine luxury and style. Much of our portfolio is privately owned, and price alone is therefore not a universal guide. We contract all our accommodation in person, and each property has its individual appeal.

To help you make the right choice based on your own priorities, we have devised a simple grading guide to be considered in conjunction with each individual property description, awarding up to a maximum of five stars for the below categories.

Grading Help

Property Grading Key:

  • 5/5

    Excellent

  • 4/5

    Very good

  • 3/5

    Good

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  • Location

    4.5/5

    Position, view, serenity, privacy

  • Comfort

    4/5

    Space, style, overall furnishings

  • Facilities*

    4/5

    Property enhancements

  • Amenities*

    4/5

    Proximity to beaches, restaurants and shops

* For further clarification on Facilities and Amenities, please view the 'Details' tab for each property or speak to one of our experienced sales consultants.

Tuscany gives you permission to indulge in life’s simple pleasures – world-famous wine, indulgent food and hours consumed by epic histories. Each of Tuscany’s ten provinces has its own unique personality, but wherever you stay, you’ll find yourself surrounded by a verdant patchwork of olive groves, cypress trees and vineyards. From the birthplace of the Renaissance, Florence, to the narrow streets of hilltop San Gimignano, Tuscany makes for a stunning escape. 

To complete the picture, explore our collection of handpicked villas, boutique Simpson Hotels and charming apartments.

Read more on our Tuscany region page



La Capannina

  • 2
  • 1
  • 1

Full details

  • Studio cottage
  • Double bedroom with en-suite shower room
  • Outdoor seating/dining area
  • Small fridge

Gli Avi

  • 4
  • 2
  • 1

Full details

  • 2-bedroom suite
  • Open-plan sitting/dining/kitchen area with open fireplace
  • Kitchen includes hob, gas oven, fridge; French door leads to large terrace for dining al fresco
  • Stairs lead up to double bedroom
  • Twin bedroom (can be configured into a double if required)
  • Shower room

La Nonna

  • 4
  • 2
  • 1

Full details

  • 2-bedroom suite
  • Open-plan sitting/dining/ kitchen area with open fire place
  • Kitchen includes hob, gas oven, fridge; French door opens to small terrace
  • Stairs lead up to double bedroom
  • Twin bedroom (can be configured into a double if required)
  • Shower room

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