Historic Estate01
Villa San BartolomeoMontepulciano · 12 guests · 6 bedrooms
From €13,125 / week
Spa · Infinity pool
The only villa in the Val d'Orcia with a private wellness centre of its own: an indoor pool heated to 38°C with hydromassage…
Villas near Cortona and the Val di Chiana
Our villas near Cortona and the Val di Chiana give you Tuscany and Umbria in one week.
3 villas
Historic Estate02
Casale di Sant'AndreaCortona · 12 guests · 7 bedrooms
From €20,700 / week
Private chef · Infinity pool
More than seventy fenced acres of its own, meadows, olive groves, a deer park, woodland walks and a private lake.
Historic Estate03
Villa della CappellaCortona · 18 guests · 9 bedrooms
From €10,150 / week
Private chapel · Frescoed interiors
A genuine 17th-century restoration: frescoed vaulted ceilings, painted walls and terracotta floors across more than 1,000 square…
Choosing the right villa
Cortona sits on its hill above the valley floor, Lake Trasimeno is about twenty minutes away, and Montepulciano is across the valley to the west. Perugia airport is about an hour away, Florence airport about 1 hour 45 minutes.
The villas
Casale di Sant'Andrea sleeps 12 on more than seventy fenced acres of its own, with olive groves, a deer park, woodland walks and a private lake.
Villa della Cappella sleeps 18 in a seventeenth-century house with frescoed vaulted ceilings and a private chapel.
Villa San Bartolomeo, near Montepulciano on the western side of the valley, sleeps 12 and has its own wellness centre with an indoor pool.
Why stay on the eastern side
This is the one part of Tuscany where Umbria is a short drive, not a long day: Lake Trasimeno, Perugia and Assisi are all within reach, alongside Cortona, Arezzo and Montepulciano on the Tuscan side. The valley is chianina cattle country, so the bistecca is local. Our Tuscany vs Umbria guide explains why this border is the answer to choosing between them.
Frequently asked
- Where is the Val di Chiana?
- In eastern Tuscany, a broad valley running from Arezzo south towards Chiusi, with Cortona on its eastern side and Montepulciano on its western edge. Umbria and Lake Trasimeno lie just to the east.
- Which airport is closest to Cortona?
- Perugia (PEG), about an hour by car, with a small European route network. Florence (FLR) is about 1 hour 45 minutes, and Rome Fiumicino (FCO) about 2 hours.
- Can you visit Umbria from a villa near Cortona?
- Yes. Lake Trasimeno is about twenty minutes from Cortona, and Perugia and Assisi make easy day trips.
See also
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