Countryside Classic01
Villa VetrichinaVal d'Orcia · 12 guests · 6 bedrooms
From €7,875 / week
Infinity pool · Pizza oven
Complete seclusion at the end of a white road through oak woods, two kilometres from San Casciano dei Bagni and its thermal…
TuscanyArea guide
Villas in Val d'Orcia, Tuscany
Rolling hills south of Siena, with Pienza, Montalcino and Bagno Vignoni among the places to visit.
16 villas in Val d'Orcia in our collection, sleeping 4 to 26 guests; 14 have a private pool and 13 list a heated pool. The largest, Tenuta La Barricaia, sleeps 26. A private chef can be arranged at every villa.
16 villas in the collection4 articles in the journal
Exclusive Villas in Val d'Orcia
The whole collection16 villas
Wellness Estate02
Tenuta La BarricaiaVal d'Orcia · 26 guests · 13 bedrooms
From €22,344 / week
Spa · Infinity pool
Thirteen en-suite bedrooms for up to twenty-six, eight in the main villa, five in a guest annex just metres away…
Countryside Classic03
Villa AgrestoCastiglion del Bosco · 12 guests · 6 bedrooms
From €91,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Spa · Heated pool
Six en-suite bedrooms for twelve, with a self-contained guest annex and kitchenette, room for a large family or group.
Countryside Classic04
Villa delle SorelleVal d'Orcia · 12 guests · 6 bedrooms
From €14,150 / week
Heated pool · Gym
A 360-degree view over the Val d'Orcia, with Pienza on the skyline and the sun setting straight across the pool.
Restored Borgo05
Casa del VescovoCastiglion del Bosco · 5 guests · 2 bedrooms
From €35,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
A 200 m² two-bedroom suite in the heart of the borgo, in timeless Florentine style.
Countryside Classic06
Villa Casa del FiumeCastiglion del Bosco · 8 guests · 4 bedrooms
From €70,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Heated pool · Pizza oven
Four en-suite bedrooms for eight, including a pool house with its own living room and bedroom.
Restored Borgo07
Casa FontacciaCastiglion del Bosco · 4 guests · 2 bedrooms
From €56,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
A detached two-bedroom suite in the heart of the borgo, with its own private entrance.
Countryside Classic08
Villa BiondiCastiglion del Bosco · 10 guests · 5 bedrooms
From €112,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Heated pool · Working vineyard
The estate's largest villa, 726 m², with five en-suite bedrooms for ten and a separate pool house.
Countryside Classic09
Villa OlivieraCastiglion del Bosco · 6 guests · 3 bedrooms
From €77,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Infinity pool · Heated pool
Three en-suite bedrooms for six, an intimate, refined house at the edge of the borgo.
Countryside Classic10
Villa GauggioleCastiglion del Bosco · 8 guests · 4 bedrooms
From €98,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Heated pool · Gym
Four en-suite bedrooms for eight, three in the main house, one in a private guest annex with its own shaded pergola.
Countryside Classic11
Villa Sant'AnnaCastiglion del Bosco · 10 guests · 5 bedrooms
From €101,500 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Heated pool · Tennis court
Five en-suite bedrooms for ten, with a separate pool house and a home-theatre room.
Countryside Classic12
Villa StabbiCastiglion del Bosco · 11 guests · 6 bedrooms
From €108,500 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Heated pool · Panoramic view
Six en-suite bedrooms for eleven, across the main house, a guest annex and a pool house.
Historic Estate13
Villa CastelloCastiglion del Bosco · 6 guests · 3 bedrooms
From €84,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Infinity pool · Heated pool
Built on medieval castle ruins, a three-storey house of real character, with a top-floor primary suite and panoramic views.
Countryside Classic14
Villa OddiCastiglion del Bosco · 12 guests · 6 bedrooms
From €91,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Heated pool · Tennis court
Six en-suite bedrooms for twelve, across the main house and a pool house, generous space for a large group.
Countryside Classic15
Villa ChiusaCastiglion del Bosco · 8 guests · 4 bedrooms
From €94,500 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Infinity pool · Heated pool
Four en-suite bedrooms for eight, including a private guest annex, and a separate pool house with a kitchenette.
Countryside Classic16
Villa AlbaCastiglion del Bosco · 6 guests · 3 bedrooms
From €63,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Heated pool
Three en-suite bedrooms for six, the most intimate of the estate's countryside villas, with a private guest annex.
On Val d'Orcia
Val d'Orcia,
from Smaranda.
The Val d'Orcia is the open country south of Siena that gave the world its idea of a Tuscan landscape, bare clay hills, single cypresses on geometric ridges, farmhouses where the painters of the Sienese school went to learn perspective. UNESCO inscribed the whole valley on the World Heritage List in 2004 not for any single monument but for the landscape itself, the only cultural-landscape inscription in Italy at that scale.
Our villas here lean grander. The Val d'Orcia is where the largest historic estates in the collection sit, fattorie of two hundred hectares with private chapels, wine cellars that doubled as defensive structures in the fifteenth century, kitchens built around dining tables that seat thirty. Contemporary studios also work seriously in the valley, and several of our Architectural Landmark listings are restorations carried out here by named practices. Several villas sit on the eastern ridge, as much Val di Chiana as Val d'Orcia, with Montepulciano and Cortona as their market towns; anyone looking for exclusive villas in the Val di Chiana will find them on this page.
Where to Stay in the Val d'Orcia
The valley organises itself around three bases, and the choice sets the tone of the week. Montalcino, on the western rise, is the Brunello town and the right anchor for a wine-led stay. Montepulciano, higher and cooler on the eastern edge, is the Vino Nobile town and the better base for the Chiana valley and Cortona. Pienza and San Quirico d'Orcia sit in the soft middle, closest to the iconic cypress-and-chapel views and the most central for moving between the two wine zones.
Our largest estates tend to sit out in the open country between these towns, on their own land with no near neighbour, which is much of the point. Tell us whether your week leans toward wine, walking or simply the view, and we will place you on the right side of the valley.
The Wine: Brunello and Vino Nobile
The valley holds two of Italy's most serious reds, and they reward scheduling rather than dropping in. Brunello di Montalcino sits on the western slope; Vino Nobile di Montepulciano on the eastern. Both are Sangiovese-based, both DOCG, both built to age. For producers worth booking a visit with: Soldera Case Basse and Biondi-Santi in Montalcino, Avignonesi and Boscarelli for Vino Nobile. For lunch between cellars, the Osteria di Casa Chianti at Castiglion del Bosco; the Locanda dell'Amorosa for an evening. We arrange the appointments, including at estates that do not take public bookings.
The Thermal Springs, and Pienza
The hot springs at Bagno Vignoni, a thermal-water village square built around an open pool dating to the Roman era, and the wilder springs at Bagni San Filippo, free, in a stream, no ticket, are within twenty minutes of every Val d'Orcia villa we hold. They are the valley's great late-afternoon habit.
Pienza, Pope Pius II's Renaissance ideal-city, is the prettiest small town in any sub-region we cover, worth a Saturday-morning walk and a pecorino bought from the cheese shops along Corso Rossellino. It is also the one place in the valley that fills at midday; come early or late.
When to come
Late April through May for the green; the valley turns gold in June. September into October for harvest and softer light. Avoid late July to mid-August unless you want company.
Towns worth knowing
- Pienza
- The Renaissance ideal-city; pecorino, vespers in the Duomo, the panoramic balcony.
- Montalcino
- The Brunello town. Vertical tastings, the Fortezza, the slow afternoon.
- Montepulciano
- Higher and colder than Montalcino; the Vino Nobile town.
- Bagno Vignoni
- Eight buildings around a Roman thermal pool. Closed early, magic at dusk.
- San Quirico d'Orcia
- Smaller than Pienza, less visited, the right place for a long lunch.
Best for
- Multi-generational family stays at the largest estates
- Serious wine weeks split between Montalcino and Montepulciano
- Photography trips and quiet anniversaries
- Returning visitors who want a different rhythm from Chianti
Plan your stay
For a golf holiday, explore Castiglion del Bosco’s estate villas and golf arrangements. Exclusive course access is a benefit of staying in a Rosewood villa; a villa elsewhere in the Val d’Orcia does not carry the same access.
Practicalities
Florence (FLR) is ninety minutes by car; Rome Fiumicino (FCO) is two hours and often the easier flight for transatlantic guests. Internal trains stop at Chiusi-Chianciano on the line from Florence to Rome.
Frequently asked
- How many villas do you have in Val d'Orcia?
- 16: Villa Vetrichina (sleeps 12), Tenuta La Barricaia (sleeps 26), Villa Agresto (sleeps 12), Villa delle Sorelle (sleeps 12), Casa del Vescovo (sleeps 5), Villa Casa del Fiume (sleeps 8), Casa Fontaccia (sleeps 4), Villa Biondi (sleeps 10), Villa Oliviera (sleeps 6), Villa Gauggiole (sleeps 8), Villa Sant'Anna (sleeps 10), Villa Stabbi (sleeps 11) and 4 more.
- Which villas in Val d'Orcia have a private pool?
- 14 of 16: Villa Vetrichina (Private 15 × 8 m infinity pool with a walk-in step entrance, fully…); Tenuta La Barricaia (Private infinity pool (15 × 5 m) above the vineyards, plus a heated…); Villa Agresto (heated private pool and outdoor Jacuzzi); Villa delle Sorelle (Private 18-metre heated saltwater pool — once the farm's animal…); Villa Casa del Fiume (heated private pool, with a pool house); Villa Biondi (heated private pool, with a pool house); Villa Oliviera (heated infinity pool); Villa Gauggiole (heated private pool, with a pool house and fitness room); Villa Sant'Anna (heated private pool, with a tennis court and pool house); Villa Stabbi (heated private pool, with a pool house), and 4 more. Tell us your dates and we will confirm which are free.
- When are the pools open in Val d'Orcia?
- Most villa pools in Tuscany open from May to late September; heated pools usually extend the season from April into October. 13 of the villas here list a heated pool (Tenuta La Barricaia, Villa Agresto, Villa delle Sorelle, Villa Casa del Fiume, Villa Biondi, Villa Oliviera and 7 more); heating can carry an extra charge, so we confirm it for your dates. Opening dates are set by each villa. In high season villas rent Saturday to Saturday.
- Which villas in Val d'Orcia suit large groups?
- 5 sleep 12 or more: Tenuta La Barricaia (sleeps 26, 13 bedrooms), Villa Vetrichina (sleeps 12, 6 bedrooms), Villa Agresto (sleeps 12, 6 bedrooms), Villa delle Sorelle (sleeps 12, 6 bedrooms) and Villa Oddi (sleeps 12, 6 bedrooms). For a celebration, ask about seated dining for the whole group and whether outside guests are allowed.
- How much does a villa in Val d'Orcia cost?
- Starting rates run from about €8,000 a week (Villa Vetrichina, sleeps 12) to about €112,000 a week (Villa Biondi, sleeps 10). Rates rise in July and August and fall in spring and autumn; each villa page shows its rates by season, and we confirm the exact price for your dates.
- Is the Val d'Orcia better than Chianti for a villa holiday?
- It is grander, quieter and more deliberate, with the largest estates and the most cinematic landscape. Choose it over Chianti for a big family gathering, a serious wine week, or a return trip that wants a slower rhythm; choose Chianti for a first visit or easier city access.
- Which town should I base near in the Val d'Orcia?
- Montalcino for Brunello and a wine-led week, Montepulciano for the cooler eastern edge and Cortona, Pienza or San Quirico for the central views and easy movement between both wine zones.
- How far is the Val d'Orcia from an airport?
- Florence is about ninety minutes; Rome Fiumicino is around two hours and often the easier flight for guests arriving from North America. A car is essential.
- Is the Val d'Orcia good for a large family group?
- Yes, particularly. It holds the collection's largest historic estates, with the space, grounds and pool privacy a multi-generational week needs.
- When is the best time to visit the Val d'Orcia?
- Late April through May for the green, September into October for harvest and softer light. The valley turns gold in June. Late July and August are hot and busier.
- Can you arrange Brunello tastings?
- Yes, including private, owner-led visits at estates in Montalcino and Montepulciano that do not accept public bookings.
Field notes on Val d'Orcia
The whole journal
Val d'Orcia
Spring in the Val d'Orcia: Poppies and When to Go
Val d'Orcia in April and May is a different region from the August postcards. Wildflowers along the SP146, the lambs, the cantinas at their easiest. The editor's view of the most photographed weeks of the Tuscan year.
Val d'Orcia
Pienza, Tuscany: What to See and Where to Eat
Pienza, the planned Renaissance city built in five years between 1459 and 1464. The pecorino, the pope, the perfect piazza, and how to use the town as part of a Val d'Orcia week.
Val d'Orcia
Montepulciano: What to See and the Cellars Below
Montepulciano: Vino Nobile, Renaissance hilltop architecture, the cantinas under the town. The editor's view of the steep, serious Tuscan town that is one of the great single-day visits in central Italy.
Val d'Orcia
The month of September in the Val d'Orcia
Why the four weeks after the heat are, quietly, the finest of the year — and what to do with them.
Compare nearby areas and alternative bases
Planning the week