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Casale dei Cipressi
The villa's warm brick and stone front with an outside staircase, tall cypresses and umbrella pines, and a table set in the shadeLooking down on a stone farmhouse with a tiled roof and blue-green shutters, cypresses and an umbrella pine in front, hills fading into the distanceA white gravel road winding between lines of cypresses over pale hills, with a small pond in the foreground

Casale dei Cipressi

A restored stone villa among olive groves and cypresses, ten minutes from Pienza in the Val d'Orcia.

4 bedrooms3 bathroomsSleeps 8Private pool
BookExplore the area

A long table under the pergola

Breakfast is on the terrace, lunch is whatever you carried back from the market in Pienza, and dinner runs on until the light has gone. The long table seats all eight of you and faces west.

Inside, thick stone walls keep the rooms cool in July and the stove warms the sitting room in November.

The sitting room, with a dark beamed ceiling, a herringbone parquet floor, armchairs and warm lamplight

Between Pienza and Monticchiello

The villa stands on a white road in the Val d'Orcia, a World Heritage landscape of clay hills, cypress lines and wheat that turns from green to gold. Pienza is about ten minutes by car, Montepulciano twenty-five, Montalcino forty-five and Siena an hour.

Evenings are for the terrace. Days are for the dairy, the abbey, the hot springs or the pool.

Golden sunset over rolling hills with a road lined with cypresses

Perfect for

Eight people, one long table and no need to be anywhere by a set time.

Groups of friends

Four bedrooms, three bathrooms and a pool mean nobody queues for anything. The kitchen table seats everyone for the first-night pasta.

Three generations

Two double rooms with their own bathrooms for the grandparents or parents, and two twin rooms for the children. There are stairs to the first floor and no lift.

Foodies

Pecorino from Pienza, Brunello from Montalcino and Vino Nobile from Montepulciano, with a kitchen big enough to cook it. Dairies, cellars and trattorie are all within 55 minutes.

Culture buffs

Pienza is a Renaissance town planned by one pope. Siena's cathedral, the abbey of Sant'Antimo and the frescoed cloister at Monte Oliveto each make a day.

Celebrations

Milestone birthdays and anniversaries for a household of up to eight, with a pergola made for long dinners. We do not allow parties or events, so evenings stay quiet.

Walkers

White roads leave from beside the villa, and the walks in the guide run from 8 to 13 km, to Monticchiello, to Sant'Antimo and to the springs.

Sleeps 8, with four bedrooms and a private pool.

Book

Our guide to the area

The places we send our own guests, with opening days checked on 13 October 2026: trattorie that close on a Monday or a Tuesday, a dairy that stays open all day, and abbeys that keep a midday pause.

Search the guideLocal secrets
The villa's warm brick and stone front with an outside staircase, tall cypresses and umbrella pines, and a table set in the shade

The house

Perfect for

Groups of friends

Groups of friends
Four bedrooms, three bathrooms and a pool mean nobody queues for anything. The kitchen table seats everyone for the first-night pasta.

Three generations

Three generations
Two double rooms with their own bathrooms for the grandparents or parents, and two twin rooms for the children. There are stairs to the first floor and no lift.

Foodies

Foodies
Pecorino from Pienza, Brunello from Montalcino and Vino Nobile from Montepulciano, with a kitchen big enough to cook it. Dairies, cellars and trattorie are all within 55 minutes.

Culture buffs

Culture buffs
Pienza is a Renaissance town planned by one pope. Siena's cathedral, the abbey of Sant'Antimo and the frescoed cloister at Monte Oliveto each make a day.

Celebrations

Celebrations
Milestone birthdays and anniversaries for a household of up to eight, with a pergola made for long dinners. We do not allow parties or events, so evenings stay quiet.

Walkers

Walkers
White roads leave from beside the villa, and the walks in the guide run from 8 to 13 km, to Monticchiello, to Sant'Antimo and to the springs.

At a glance

Sleeps 8Four bedrooms and three bathrooms.
Private poolOpen late May to late September. Unheated, not fenced and without a lifeguard.
WifiIn the house. We will send you your network details in your welcome message before you arrive.
ParkingFour cars on the gravel court in front of the house.
Heating and coolingA wood-burning stove in the sitting room, radiators, and air conditioning in the bedrooms.
Washing machineIn the house, with a drying rack and a line on the terrace.
KitchenDishwasher, oven, hob, and moka pots for the morning.
BarbecueBuilt in by the pergola. Please bring your own charcoal.
We meet youOne of us welcomes you from 16:00 and hands over the keys.
High chair and cotA high chair and a travel cot, on request.
PetsWelcome on request, and kept out of the pool.

A restored villa of warm Tuscan brick and stone with four bedrooms, three bathrooms and a private pool above an olive grove. The rooms are cool and beamed, the floors are stone and parquet, and every window looks at hills or cypresses.

A turquoise pool edged in terracotta, with loungers, a large terracotta urn, red dahlias in the foreground and olive groves and vines beyond
The pool, with olive groves and vines beyond
The sitting room, with a dark beamed ceiling, a herringbone parquet floor, armchairs and warm lamplight
The sitting room
A kitchen with white tiled walls, a long timber table with stools, a woven pendant lamp and copper pans on a rail
The kitchen and its long table
A vaulted corridor with a stone floor, arched doorways and a lantern, ending in a small window
The vaulted hall
An arched entrance with an open timber door, a lantern overhead and a view of trees outside
The entrance
A gravel track beside a stone outbuilding under umbrella pines, with a row of cypresses, a lawn and the pool in the distance
The grounds, with the pool beyond the pines

Bedrooms

A double bed with a pale wooden headboard and rust-coloured cushions, a woven pendant light and a tall window in a white room

Bedroom 1

First floor Double bed, a tall window onto the olive grove and its own bathroom.

A bed with a woven headboard screen, a wooden bench, a jute rug and a large plant in a white room with a dark ceiling beam

Bedroom 2

First floor Double bed with a day bench, a jute rug and its own bathroom.

A tall shuttered window open onto a lawn and a green hill, in a room with a dark ceiling beam

Bedrooms 3 and 4

First floor Two twin rooms, with single beds that can be pushed together into a double on request. They share a bathroom, and tall shuttered windows look onto the lawn.

In the house

  • Four bedrooms and three bathrooms
  • Private swimming pool, late May to late September
  • Pergola with a long table for eight
  • Built-in barbecue by the pergola
  • Wood-burning stove in the sitting room
  • Air conditioning in the bedrooms
  • Washing machine and dishwasher
  • Wifi throughout
  • Desk on the landing, looking at the olive grove
  • High chair and travel cot
  • Bed linen, towels and pool towels
  • Parking for four cars on the gravel court
  • Olive grove and lawn

Stay your way

Choose a topic.

Where everyone sleeps

Bedrooms 1 and 2 have double beds and their own bathrooms. Bedrooms 3 and 4 have twin beds and share a bathroom. A travel cot fits in any room.

In the house

  • High chair
  • Travel cot
  • Pool towels

Good to know

  • The pool is not fenced and has no lifeguard. An adult must be at the water whenever children are in or near it.
  • Stone stairs lead to the first floor and there is no lift.
  • The terrace is shaded by the pergola in the afternoon heat.

Dogs are welcome by arrangement, and stay out of the pool. <a href="#ask">Tell us about your dog</a> before you book. The places below are tagged as welcoming dogs in the guide.

What is here

  • Wifi in the house.
  • The desk on the landing looks onto the olive grove.

Video calls

It is a countryside connection and we have not published a speed. If you need steady video calls, ask us before you book.

Green hills under a sunset sky with a winding road lined with cypresses

Explore the Val d'Orcia

The places we send our own guests, mixing the famous towns with a dairy, a trattoria and a few quiet roads. Opening days and hours were checked on 13 October 2026. Italian places often close one day a week and for the afternoon, and many shut for part of August and for weeks in January and February, so look at the hours on each card and book the evening before.

Culture

Ready-made days

Half-day trips

Each trip is a half day or a day. Drive times are from the villa, rounded, and hours were checked on 13 October 2026 where the trip says so.

Further afield

Siena, Monte Oliveto and the hot springs are about an hour away. Each is worth a day, so start early and eat lunch there.

Walks, water and wildlife

Walks leave from the road beside the villa or a short drive away, and the springs are the other kind of exercise. Gardens and a famous view are below.

Hot springs

On foot

Gardens and views

Through the year

Opening hours shift with the season: abbeys and gardens keep longer days in summer, and many trattorie close for some weeks in January or February. Checked on 13 October 2026.

A small chapel and farmhouse on a green hill with a wooded ridge behind

Spring

At the house

  • The wheat is bright green and the poppies line the lane. The pool is still too cold, so eat outdoors at midday.

Nearby

  • La Foce's guided garden visits start in April (the 2026 season ran from 1 April to 28 October).
  • Walks are at their best from April to early June, before the heat.
A turquoise pool edged in terracotta, with loungers and red dahlias, and olive groves beyond

Summer

At the house

  • The pool is open and evenings on the terrace run late. The stone walls keep the bedrooms cool.

Nearby

  • Montepulciano's Cantiere Internazionale d'Arte runs in late July and early August (20 July to 2 August in 2026).
  • Siena's Palio is run on 2 July and 16 August.
  • Many shops and restaurants close for a week or two around Ferragosto, 15 August: ask before you drive.
Pale harvested hills with a white road lined with cypresses and a small pond

Autumn

At the house

  • The grape and olive harvests happen around the villa, the light turns amber and the stove is lit in the evening.

Nearby

  • Pienza's Fiera del Cacio, the pecorino fair, runs in the first week of September (31 August to 6 September in 2026).
  • The white truffle fair at San Giovanni d'Asso runs on two weekends in November; the dates change each year.
  • On 1 November the abbey of Sant'Antimo and Siena cathedral move to winter hours, and Siena's marble floor is covered again after 31 October.
Pale hills in morning mist with a hilltop farmhouse ringed by cypresses

Winter

At the house

  • The stove in the sitting room, long lunches and quiet roads. The pool is closed.

Nearby

  • Palazzo Piccolomini is closed 16 to 30 November and 7 January to 14 February.
  • The free hot springs at Fosso Bianco are open all year, although the Terme San Filippo spa is closed for restoration.
  • Some trattorie close for weeks in January or February: always ask first.

Plan your day

Tap the places you would like to see and we will draw you a route from the house, then work out roughly how long it takes. You can save the result as a picture for your phone.

Drag the map sideways. Tap a pin for details.

Drawn by hand and not to scale. A dashed ring means further afield. Place positions are approximate.

Your day

Nothing chosen yet. Tap a place on the map, or pick from the list below it.

All the places

The same places as the map, as a list. Choose any of them.

Terracotta roofs of a hill town under a cloudy sky, with hills beyond

Local secrets

Eight things most visitors to the Val d'Orcia walk past.

A town built by one pope

Pienza was a village called Corsignano until Pius II, who was born there, had it rebuilt from 1459 around a single square. UNESCO listed the centre in 1996.

Pecorino in walnut leaves

Caseificio Cugusi ages pecorino in walnut leaves, hay, bran and ash. Taste them side by side at the counter, because the rind changes everything.

Hot water for free

At Fosso Bianco in Bagni San Filippo a 48-degree spring cools down a white limestone gully into pools. It is free and open all year.

A pool for looking at

The steaming basin in Bagno Vignoni's square is a sixteenth-century tank, and Saint Catherine of Siena and Lorenzo de' Medici were among the spa's visitors. Nobody may bathe in it now.

A theatre where the village is the cast

Since 1967 the people of Monticchiello have staged a play about their own lives each summer. The 2026 play was the sixtieth.

Cypress avenues are private

The cypress drive at Poggio Covili is on private land: photograph it from the entrance. The Baccoleno avenue, on the road toward Siena, belongs to an agriturismo.

The garden in a war diary

La Foce, the garden in Iris Origo's War in Val d'Orcia, opens for guided visits on Wednesdays and Sundays until 28 October 2026.

The floor that is usually covered

Siena cathedral's inlaid marble floor is covered for most of the year and uncovered for a few months. In 2026 it is on view until 31 October.

Sources, checked 13 October 2026: Wikipedia (Pienza, Bagno Vignoni), caseificiocugusi.it, bagnisanfilippoterme.it, visittuscany.com, La Nazione (Teatro Povero), 22places.com and italia-by-natalia.pl (cypress avenues), lafoce.com, operaduomo.siena.it. The Saint Catherine and Lorenzo story is from Wikipedia.

A stone square with a well-head fountain, awnings and café tables in the sun

Culture

The Val d'Orcia was shaped by pilgrims on the Via Francigena, by Sienese bankers and painters, and by one pope who rebuilt his birthplace as an ideal town. Here are books to read, painters and monks, and the films that made the hills famous.

Books set here

Two books to read before you come, one from the valley itself.

War in Val d'Orcia

Iris Origo · 1947

Her diary of 1943 to 1944, written at La Foce while she sheltered children and refugees close to the front line.

Under the Tuscan Sun

Frances Mayes · 1996

A memoir of restoring a villa near Cortona, about an hour east of here in the Val di Chiana.

History, art and music

A pope who rebuilt a village, and a tradition of chant.

Pius II, 1405 to 1464
Born Aeneas Silvius Piccolomini in Corsignano, he became pope in 1458 and had his birthplace rebuilt as an ideal Renaissance town, renamed Pienza.
Gregorian chant and the Cantiere
The monks of Sant'Antimo and Monte Oliveto sing the daily offices, and Montepulciano's Cantiere Internazionale d'Arte, founded by Hans Werner Henze, fills the town with music each summer.

Artisans and makers

In the Val d'Orcia the craft is mostly food and monks.

Pecorino di Pienza
Sheep's milk cheese made around Pienza, eaten fresh or aged for months, sometimes in walnut leaves, hay or ash. Cugusi has made it since 1962.
The monks of Monte Oliveto
The abbey's Benedictine monks sell their own wine and monastic products from the abbey.

Makers and galleries to visit today

Film and TV

Two films that used the hills around Pienza.

Romeo and Juliet, 1968
Franco Zeffirelli filmed the Capulet party in Palazzo Piccolomini, on Pienza's main square.
Gladiator, 2000
The gravel road from the Pieve di Corsignano to Terrapille, just outside Pienza, was filmed as the road through the Elysian Fields in Ridley Scott's film.

Places to visit

Open as listed on 13 October 2026; the cards show the days.

A gravel track beside a stone outbuilding under umbrella pines, with a row of cypresses, a lawn and the pool in the distance

Stay with us

Send us your dates and we will reply by email to confirm, or book through the booking link on this page.

Request your datesBook your stay
The villa's warm brick and stone front with an outside staircase and tall cypresses

Send us your dates

Tell us when you would like to stay and how many of you are coming. We reply by email to confirm. Nothing is charged on this site.

We use your details only to reply about your stay.

At a glance

Sleeps 8Four bedrooms and three bathrooms.
WifiIn the house.
ParkingFour cars on the gravel court.
Heating and coolingA stove, radiators and air conditioning in the bedrooms.
We meet youFrom 16:00, at the villa.
PetsWelcome on request.
Everything in the house

Getting here

Times are by car to the villa without traffic, rounded. Allow extra on Friday and Sunday evenings on the A1 motorway, which has tolls, and on the Cassia road behind farm traffic.

FlorenceAbout 2 hoursAbout 125 km
RomeAbout 2 hours 45 minutesAbout 200 km
Pisa airportAbout 2 hours 15 minutesAbout 165 km

By train

  • Chiusi-Chianciano Terme is the nearest main-line station, about 35 km away. Regional trains call there; check the timetable for others.
  • We do not know a bus we can recommend for the last stretch. Most guests hire a car in Florence or Rome, because a car is the sensible way to stay here.

Parking

At the villa there is room for four cars on the gravel court. In Pienza, Montepulciano, Montalcino and Siena the historic centre is a limited traffic zone (ZTL): park outside the walls.

Distances and times are rounded estimates from road distances, not read from a live route planner on 13 October 2026. Allow extra, and check your route before you travel.

Questions people ask

Booking and your stay1
When are check-in and checkout?
Check-in from 16:00 and checkout by 10:00. One of us meets you at the villa. If you land late, tell us and we will either wait or agree a lockbox with you in advance; the details come in your booking message.
Getting here and parking1
Where do we park?
Four cars fit on the gravel court. The last stretch is a white gravel road. Hire cars manage it, but drive slowly after rain.
Around the house3
Is there a pool?
Yes, a private pool for house guests, usually open from late May to late September. It is unheated, not fenced and has no lifeguard.
How do the heating and fire work?
There is a wood-burning stove in the sitting room, with logs by the door, and radiators in the house. We show you the stove at check-in. In summer the bedrooms have air conditioning.
Is the wifi good enough to work?
Wifi works throughout the house. It is a countryside connection, so we do not promise speeds. If you need video calls, ask us before you book.
Out and about2
When do shops and restaurants open?
Many shops close from about 13:00 to 16:00 and on Sunday afternoons. Restaurants serve lunch from about 12:30 to 14:30 and dinner from 19:30, and rarely open in between. Most close one day a week, many close for a week or two around Ferragosto (15 August), and some close for weeks in January or February. Each place in the guide shows its days.
Can we drive into the old towns?
Rarely. Pienza, Montepulciano, Montalcino and Siena restrict cars in the historic centre (a ZTL). Park outside the walls and walk, because fines arrive by post months later.
Food and shopping1
Where is the nearest supermarket?
There is a Coop in Pienza, about ten minutes away, and another in Montalcino. Pienza also has a Friday morning market. Shop on Saturday for Sunday.
Dogs1
Can we bring the dog?
Please ask first. Dogs are welcome by arrangement, stay out of the pool and off the beds. Tell us the breed and size when you ask.
Families and little ones1
Do you have a cot, high chair or stair gates?
We have one high chair and one travel cot, both free. Tell us before you arrive and we will set them up. We do not have stair gates, and the first floor is up stone stairs.

Ask Chiara and Matteo a question

Thinking of staying, or planning a stay? Send us your question and we will reply by email.

We use your details only to answer your question.

An arched entrance with an open timber door, a lantern overhead and trees visible beyond

Guests

This section covers your stay from arrival to checkout. Door codes, key-safe numbers and the wifi password are in your welcome message and are never published here.

Extras

Arrival

  1. Drive to the villa using the pin in your booking message. The last stretch is a white gravel road.
  2. Park on the gravel court in front of the house, up to four cars.
  3. One of us meets you from 16:00, shows you the stove, the pool and the bins, and hands over the keys.
  4. Arriving late? Tell us beforehand. We will either wait or agree a lockbox with you; its details come in your booking message and never appear on this site.
  5. Shops close for the afternoon and on Sunday. Buy bread, milk and wine for the first night on your way in.

House manual

Also searchable from the site search.

Safety

  • Emergencies: call 112, the single European number, for police, ambulance and fire. For an ambulance alone, call 118.
  • The nearest emergency department is at the Nottola hospital near Montepulciano, about 25 minutes away. Check the route before you need it.
  • The pool is not fenced and has no lifeguard. Children must be watched at all times.
  • The stove glass gets very hot. Never leave the stove unattended with its door open.

Nearby essentials

The duty pharmacy (farmacia di turno) for nights and Sundays is posted on every pharmacy door and listed at lanazione.it/siena/farmacie. We keep the number of a local driver on the kitchen board; ask us if you need one.

House rules

  • Up to 8 guests.
  • Pets by arrangement. Please ask first.
  • Smoking outside only, please.
  • No parties or events.
  • Quiet from 23:00, please.
  • Please shower before using the pool, and no glass at the poolside.
  • Please shower before using the pool, and no glass at the poolside.

Departure

Please leave by 10:00. Close the shutters and windows, switch off the air conditioning and lights, let the stove go cold, sort the rubbish into the bins by the gate (raccolta differenziata), and leave the keys on the kitchen table.

A pergola with white drapes and wicker armchairs beside a pool, with loungers on the lawn beyond

Extras

Local businesses you can book yourselves, for a cooking class, a transfer, a tasting or food to take home. We have not checked prices or availability.

These are independent third parties. We don't provide, book or endorse them. Please check details and prices with them directly.

Cooking classes and meals

  • Ristorante Daria, MonticchielloA family restaurant that also runs cooking classes. Ask what is on offer.
  • Podere Il Casale, PienzaAn organic farm with a restaurant, cooking classes and cheese tastings.

Taxis and airport transfers

  • BlueKeys ElitePrivate transfers with a driver at a fixed price per vehicle, quoted online, including Pienza to the Rome airports and stations. Based near Naples, so book well ahead.
  • A local driverWe keep the number of a driver from Pienza and Montepulciano on the kitchen board.

Things to book

  • La Foce gardenGuided visits only, booked online. The 2026 season ends on 28 October.
  • ArgianoPrivate cellar visits and tastings in the Villa Bell'Aria, booked on its website.
  • Poggio AnticoWinery tours and tastings in Montalcino, booked on its website.
  • Caseificio CugusiTastings at the dairy, and picnics booked online in the warm months.

Food and groceries

  • Caseificio CugusiSells pecorino at the counter and ships from an online shop.
  • Salumeria Gastronomia del Corso, PienzaA deli with its own salami and prosciutto, plus pecorino, wine and sandwiches.
  • La Taverna del Pecorino, PienzaA shop and tasting room for pecorino, salami, olive oil and balsamic vinegar on Via Condotti.
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