Historic Tuscan Estate

Situated in exceptionally picturesque countryside, Montestigliano has all the characteristics of the classic Tuscan Great Estate: avenues of cypresses, vineyards, olive groves, woodlands and neat, cultivated fields. We have been renting this jewel of a Tuscan hamlet since the very beginning, in the 80s and it is still as beautiful today as it was then, albeit with more mod cons!

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italia > toscana > siena

Virginia B

Posti letto: 4
€ 800 - € 1100 a settimana.

italia > toscana > siena

Virginia A

Posti letto: 4
€ 980 - € 1600 a settimana.

italia > toscana > siena

Villa Luisa

Posti letto: 10
€ 1850 - € 3490 a settimana.

italia > toscana > siena

Villa Donati

Posti letto: 14
€ 2140 - € 4400 a settimana.

italia > toscana > siena

Ropoli Sotto

Posti letto: 6
€ 1000 - € 1850 a settimana.

italia > toscana > siena

Ropoli Sopra

Posti letto: 4
€ 840 - € 1300 a settimana.

italia > toscana > siena


Posti letto: 4
€ 1100 - € 1800 a settimana.

italia > toscana > siena


Posti letto: 6
€ 1150 - € 2070 a settimana.

italia > toscana > siena


Posti letto: 4
€ 1200 - € 2000 a settimana.

italia > toscana > siena


Posti letto: 3
€ 800 - € 1250 a settimana.

italia > toscana > siena


Posti letto: 4
€ 980 - € 1600 a settimana.

Aerial drawing of Montestigliano Dan Wrightson's sketch of Montestigliano

The estate buildings form a small complex with some farmhouses, the villa and agricultural buildings in a beautiful position on top of a hill. There are extensive views of the surrounding countryside. Wide, sandy, cypress-lined avenues traverse the forested hills of the estate, often terminating in belvederes at the most impressive viewpoints. Through the tangled woodlands, across the cultivated plain below, one can see Siena and the Chianti hills in the distance. The estate is surrounded by a rare abundance of wild flowers and animals. There is a wonderful article about Montestigliano on the Hole in the Donut. The author, Barbara Weibel, describes how:

... in 1985, a tourist agent in London convinced the family that many people would love to stay at a working holiday farm in Tuscany."

That "tourist agent" was my mother, and she wasn't in London, we lived about 20 minutes away near the village of Casole d'Elsa - but it was my mother's idea that the estate should start converting and renting out the empty farmworkers' buildings. We're proud to still be working with Montestigliano today and have seen families come to stay with their new-borns, and those same new-borns return, all grown up, to get married on the estate!

Perfect for families.

Some of the farmhouses on the vast Montestigliano estate have been very carefully converted into pleasing, comfortable houses and apartments. Guests on the estate share two swimming pools, one reserved for those who want peace and quiet, the other further from the houses, allowing free rein to summer holiday fun.

Wild swimming and Historic Cloisters

Guests at all the properties may wander at will all over the estate. Part of the lands front the River Merse, which has excellent swimming and is protected for bathers by the Sienese authorities. The tiny village of Torri, with its famous monastery and striped cloisters is two minutes away by car, while there are pizzerie and restaurants within a few minutes' drive. A very important extra here is provided by the charming owners who will unobtrusively keep out of your way or happily go out of their way to help you, providing endless extra services if you require them, from sending faxes, arranging balloon trips, providing touring information, to translating at the doctor's.

Cloister at Torri
The striped cloister of Torri, near Rosia and Siena

Summer Events

During the summer concerts and exhibitions are often organised in the ancient granary, an extraordinary lofty space (14 X 28 m.) spanned by great arches laced with tie bars.

This barn is also very suitable as studio space for art courses or conferences, and the rooms below, next to the estate offices, include a games room with billiards, TV, ping pong, a dining room, a catering kitchen and a small gift shop. The little restaurant provides delightful suppers twice a week.

Fantastic for weddings

We have numerous weddings here and it is a great venue. Large enough for 60 or 70 guests, with plenty of spaces for meals, ceremonies and dancing. Montestigliano has its own chapel too, to make the moment extra special.

And in case you're wondering, we've had plenty of same sex ceremonies here too - Italy is LGBTQ+ friendly and Montestigliano is doubly so.

This is the second time we have stayed there and it is a wonderful place. Tuscany is beautiful and this villa is in the middle of all this beauty. It is exactly what we were expecting from a Tuscan villa. Rustic feel; amazing family who own it and the manager Francesco is a wonderful host for anyone staying there. He is most attentive and looks after everyone. The views first thing in the morning over the valley are stunning, especially as the mist clears.

LB, NF and FriendsVilla Donati

Lovely villa. Plenty of space for the 10 of us. I loved the peace and tranquility of this place yet it was within easy reach of many nearby places of interest especially Siena which was only a few miles away. Car is really essential as location is right in middle of countryside. Beautiful views from villa of surrounding Tuscan hills.Family run holiday accommodation and all staff were friendly and helpful. Decor very rustic which gave an authentic feel to a tuscan villa.

Mrs LV and familyCasa Luisa

We had a fantastic stay - such a beautiful setting and really friendly, helpful people - many thanks!

Mrs AB and familyVirginia B

We loved it. The villa, the pools, the hosts, the location were all fantastic. We loved the nights in the piazza and enjoyed exploring Siena as well. It really was a fantastic week! R. W. Ropoli Sotto

Montestigliano from a distance This is Montestigliano seen from a distance Villa Donati Villa Donati’s facade shows its years, with faded yet still strong burnt sienna plaster

living room in Villa Donati Living room in Villa Donati The living room in Villa Donati has old world elegance

Quiet pool in Donati There are 2 pools – this is the quiet one

Virginia montestigliano Virginia A and B occupy the top floor of this ancient farmhouse

Contact us about Montestigliano