Where to Stay
Ten places to stay in Chianti — from castle
relais to rooms above village restaurants.
Accommodation in Chianti ranges from grand Relais & Châteaux properties within medieval castle walls to simple agriturismo rooms on working wine estates. In all cases, location matters — choosing where to sleep shapes which villages, cellars, and restaurants you reach most easily. These ten are our personal recommendations, spanning all budgets and styles.
Relais & Châteaux · 12th Century Castle
A Romanesque pieve and castle complex transformed into one of the zone's most intimate luxury hotels. The Michelin-starred restaurant Il Pievano draws guests from across Tuscany; the cellar is exceptional. Rooms in the converted castle buildings retain thick stone walls and remarkable stillness.
spaltenna.it · +39 0577 749483 · Gaiole in Chianti, SI · Check availability →
Boutique Villa · Scottish-Owned
Perched on the slopes above Greve, Villa Bordoni is a labour of love by Scottish owners David and Catherine Gardner. Eight rooms, a small pool, an outstanding wine list, and cooking that consistently outperforms properties twice the size. The views from the terrace at sunset are worth the journey alone.
villabordoni.com · +39 055 854 6230 · Mezzuola, Greve in Chianti, FI · Check availability →
Marriott Autograph Collection · Wine Resort
An entire medieval hamlet — hamlet, church, olive press, and all — converted into one of Tuscany's finest wine hotels. 56 rooms and suites across its historic buildings, two pools, a spa, and the Michelin-starred Poggio Rosso restaurant. The estate also produces well-regarded Chianti Classico under the Agricola San Felice label.
borgosanfelice.com · +39 0577 3964 · Loc. San Felice, Castelnuovo Berardenga, SI · Check availability →
Abbey Agriturismo · Self-Catering
Stay within the grounds of the 11th-century Benedictine abbey that produces some of Chianti Classico's most elegant wines. Apartments in the converted monks' quarters sleep two to six, with access to the gardens and the estate's oil and wine. Cooking courses run by the Stucchi Prinetti family are legendary.
coltibuono.com · +39 0577 74481 · Badia a Coltibuono, Gaiole in Chianti, SI · Check availability →
Historic Podere · Boutique Resort
A 14th-century podere on 123 acres of meadow, vine, and olive above the Pesa valley, restored with quiet confidence into one of the most intimate luxury properties in Chianti. With only six rooms and a four-bedroom villa, there are never more than 22 guests on the estate — a scale that allows a level of personalised attention rare in any category. The restaurant, Il Sorbo 1384, is a serious draw in its own right: an à la carte kitchen drawing on the kitchen garden and local producers, housed in a setting of extraordinary stillness. The infinity pool looks out over an unbroken arc of Chianti hills.
podere1384.it · +39 0577 1722565 · Castellina in Chianti, SI · Check availability →
Medieval Castle · Agriturismo
Authentic and wonderfully atmospheric — a working medieval castle with rooms in the converted outbuildings and one unforgettable suite within the 11th-century tower itself. The estate produces its own Chianti Classico, and the views from the tower over the valley are remarkable. One of the most honest and characterful places to stay in the zone.
castellotornano.it · +39 0577 746067 · Gaiole in Chianti, SI · Check availability →
Relais de Charme · Wine Estate Borgo
A restored hilltop farmstead set directly within the Tenute del Cabreo estate, between Greve and the walled medieval hamlet of Montefioralle — birthplace of Amerigo Vespucci. Opened in 2017 by Giovanna and Francesca Folonari, whose family has been one of Tuscany's leading wine dynasties for over a century, the property takes its name from Cabreo Il Borgo, the estate's flagship SuperTuscan blend first produced in 1982. Eleven rooms in the converted borgo overlook vine and cypress; dinner in the adjacent Cabreo restaurant is reserved exclusively for Relais guests.
borgodelcabreo.it · +39 055 3985032 · Greve in Chianti, FI · Check availability →
Historic Village Villa · Boutique Guesthouse
An ancient villa set in the heart of Panzano's medieval village — its entrance on the old Chiantigiana, its rear opening onto a sweeping panorama of Chianti hills. Five individually designed rooms in the restored main house, plus a converted barn annex with direct vineyard views over Montefioralle. A heated pool, two-level garden, and wood-burning terrace; an unusually rich programme of curated experiences — private winery visits, wine dinners, cooking school. The entire villa may be taken exclusively.
villalapetraia.com · +39 333 9591881 · Panzano in Chianti, FI · Check availability →
Della Robbia Estate · Historic Boutique Hotel
The former summer retreat of the della Robbia dynasty — the great Florentine sculptors whose terracotta works adorn the adjacent Romanesque Pieve di San Leolino — converted in 1976 into one of the first boutique hotels in Chianti. Count and Countess Aloisi de Larderel live on the property and greet guests personally, running it with the attentiveness of a private house rather than a hotel. The restaurant, Il Torchio, is set in the estate's original wine press room; the salt-water infinity pool, lined with travertine, looks out over the golden bowl of the Conca d'Oro. No televisions in rooms.
villalebarone.com · +39 055 85 26 21 · Panzano in Chianti, FI · Check availability →
Rural Hotel · Thermal Spa
A beautifully positioned rural hotel between Castellina and Siena, with a thermal outdoor pool, a full spa, and panoramic views across the vines and cypress hills of the Chianti Classico zone. The restaurant sources ingredients from the estate and from neighbouring farms. Ideal for those who want comfort and stillness in equal measure.
lefontanelle.com · +39 0577 740194 · Castellina in Chianti, SI · Check availability →