Some places invite you to slow down the moment you arrive — not through remoteness, but through atmosphere.
Self-catering Residence
Countryside
Cultural, Family, Food & Wine, Hiking
A Private Hilltop Hamlet for Families, Groups & Independent Travellers
Some places invite you to slow down the moment you arrive — not through remoteness, but through atmosphere.
Montestigliano is one of those rare estates: an 18th-century hilltop hamlet restored with quiet devotion, wrapped in olive groves and soft Tuscan light.
Perfect for families, small groups, and travellers who value space and independence, this private estate offers self-catering villas and apartments that blend rustic character with thoughtful comfort.
It’s a place for long evenings outdoors, unhurried mornings, and the quiet luxury of living like a local.
Authentic Tuscan Hamlet: A family-owned estate with restored farmhouses, traditional architecture, and centuries-old rural charm.
Flexible Self-Catering Freedom: Villas and apartments with full kitchens, terraces, gardens, and spacious indoor–outdoor living.
Two Panoramic Pools: Wide views, quiet areas for adults, and safe open spaces for children.
Seasonal Estate Experiences: Pizza nights, olive oil tastings, communal dinners, and farm-to-table collaborations.
Ideal for Families & Groups: Generous living spaces, privacy between units, and large outdoor areas for gathering and play.
Close to Siena & Crete Senesi: A peaceful base with easy access to Tuscany’s medieval towns, wineries, and scenic landscapes.
9 apartments
£ 2700 for Casa Massimo (sleeps 4)
Travel planning
7 nights self catering
Fully comprehensive car hire arranged at the airport
We often pair Albergo Etico in Rome with Montestigliano for a journey that begins in the cultural vibrancy of the Eternal City before settling into the calm, open landscapes of rural Tuscany. Contact us to explore all the ways to combine this stay with other refined locations.
A former Vin Santo drying room, now a warm apartment with two connected living rooms, an open fireplace, a well-equipped kitchen, and two en-suite bedrooms. A private garden framed by olive trees offers pergola dining and beautiful sunset light.
A first-floor farmhouse apartment with terracotta floors, whitewashed walls, and a traditional Tuscan fireplace. The south-facing balcony is ideal for aperitivo, while the lawn below is perfect for children’s games and pergola dining.
A compact sister apartment to Virginia 1. Features an open-plan living area, two bedrooms, one bathroom, a sunset-facing balcony, and a garden with pergola and barbecue.
The most intimate of the lower-hamlet villas, with wide valley views. The open-plan living area includes a fireplace, and the villa’s standout feature is its large outdoor kitchen–dining terrace and peaceful south-east facing garden.
A bright first-floor villa accessed via an outdoor stone staircase. The furnished terrace overlooks the valley. Indoors, an open-plan living area centres on an original fireplace, with two bedrooms and a bathroom.
A spacious three-storey villa with rustic charm. Features include an Etruscan cellar, a living–dining room, generous bedrooms, multiple bathrooms, and a covered terrace with a wood-fired oven — ideal for long summer evenings and homemade pizza.
A private villa blending restored Tuscan character with contemporary design. Large sliding doors open to a furnished terrace with outdoor fireplace and wide views. Both bedrooms are en suite. A quiet hideaway close to the hamlet.
A bright, spacious first-floor farmhouse in the heart of the hamlet. Includes a large living room with a wood burner, kitchen–dining area, three bedrooms, and two bathrooms. The rear garden has a wisteria pergola and open views over olive groves.
A generous farmhouse ideal for larger families or groups. A stone staircase leads to a covered loggia terrace with sunset views. Inside, the open-plan kitchen and living areas connect naturally. Five bedrooms, four bathrooms, and a second rear terrace complete this spacious, private home.
Cook at home or explore nearby trattorie in Sovicille and Siena.
Montestigliano hosts relaxed communal evenings throughout the week, perfect for families and groups.
Generous Tuscan grills with pork ribs, sausages, chicken, salads, pasta, and bruschette. Sunset dining with views across the hills.
Wood-fired pizzas by Damiano served slice after slice — margherita, meat feast, vegetarian, and the estate-favourite Nutella pizza. A lively, family-friendly evening.
Hands-on classes led by the estate chef, teaching simple, authentic Tuscan dishes using fresh local ingredients. Suitable for adults, children, or families.
Learn to taste and compare oils with Massimo, the estate farmer. November guests can join the olive harvest and visit the local frantoio for freshly pressed oil.
✔ Two panoramic pools: the “Quiet Pool” for adults to read, and the ‘Noisy Pool’ for families.
Gardens, olive groves, walking paths
✔ Seasonal tastings & pizza nights
✔ Barbecue and pizza oven areas
✔ On-site concierge
✔ Family-friendly outdoor spaces
✔ Fully equipped kitchens
✔ Indoor/outdoor dining areas
✔ Air conditioning (in many units)
✔ Wi-Fi
✔ Terraces or private gardens
✔ Washing machines (varies by unit)
Restored 18th-century rural architecture
Low light pollution — superb stargazing
Estate-produced olive oil
Sustainable energy practices
Perfect for retreats, families, and small groups
📍 Siena — 20 minutes: Medieval architecture, art, and lively evenings
📍 San Gimignano — 45 minutes: Towers, gelaterie, Vernaccia
📍 Crete Senesi — 25 minutes: Photogenic clay hills and scenic drives
📍 Monteriggioni — 35 minutes: Perfectly preserved medieval citadel
📍 Montalcino — 45 minutes: Brunello wineries and Val d’Orcia vistas
📍 Abbey of San Galgano — 25 minutes: Roofless abbey and the sword in the stone