A stone Tuscan villa with a cypress-lined pool at golden hour, Chianti hills in the background

Where to Stay

Rest Among
the Vines

Places to stay in Chianti — from castle relais to rooms on working wine estates.

Accommodation in Chianti ranges from grand luxury hotels 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 are our personal recommendations, spanning all budgets and styles.

Stone-walled castle exterior of Castello di Spaltenna in Gaiole in Chianti
Gaiole in Chianti €€€€

Castello di Spaltenna

Small Luxury Hotels of the World · 12th-Century Castle

A Romanesque pieve and castle complex transformed into one of the zone’s most intimate luxury hotels, with some 38 rooms. Il Pievano, holder of one MICHELIN star under chef Antonio Iacoviello, draws guests from across Tuscany; the cellar is exceptional. Rooms in the converted castle buildings retain thick stone walls and remarkable stillness.

  • Pool
  • Spa
  • MICHELIN-starred restaurant
  • Wine cellar
  • Vineyard views

spaltenna.it  ·  +39 0577 749483  ·  Read more →

The vine-covered terrace of Villa Bordoni boutique hotel above Greve in Chianti
Greve in Chianti €€€

Villa Bordoni

Boutique Villa · Restaurant Il Guardingo

Perched on the slopes above Greve, Villa Bordoni is unmistakably a labour of love — the kind of house where every room and every plate feels personally considered. Eleven rooms, a small pool, an outstanding wine list, and in its restaurant, Il Guardingo, cooking that consistently outperforms properties twice the size. The views from the terrace at sunset are worth the journey alone.

  • Pool
  • Il Guardingo restaurant
  • Wine list
  • Panoramic terrace

villabordoni.com  ·  +39 055 854 6230  ·  Read more →

The stone piazza of Borgo San Felice, a medieval hamlet converted into a five-star hotel
Castelnuovo Berardenga €€€€€

Borgo San Felice

Relais & Châteaux · Wine Resort

An entire medieval hamlet — church, olive press, and all — converted into one of Tuscany’s finest wine hotels, a member of Relais & Châteaux since 1992 and owned by Allianz. More than 60 rooms and suites across its historic buildings, two pools, a spa, and two MICHELIN Keys. Poggio Rosso holds one MICHELIN star and a Green Star, with chef Stelios Sakalis in the kitchen since July 2025 as part of Enrico Bartolini’s group; Osteria Il Grigio is the more relaxed alternative. The estate also produces well-regarded Chianti Classico under the Agricola San Felice label.

  • Two pools
  • Spa
  • MICHELIN-starred restaurant
  • Own winery
  • Tennis

borgosanfelice.com  ·  +39 0577 3964  ·  Read more →

Stone-vaulted rooms of the agriturismo at Badia a Coltibuono, an 11th-century Benedictine abbey
Gaiole in Chianti €€

Badia a Coltibuono — Agriturismo

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.

  • Self-catering
  • Abbey gardens
  • Cooking courses
  • Estate wine

coltibuono.com  ·  +39 0577 74481  ·  Read more →

The infinity pool of Podere 1384 suspended above Chianti hills and vineyards near Castellina
Castellina in Chianti €€€€

Podere 1384

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.

  • Infinity pool
  • Spa & sauna
  • Il Sorbo restaurant
  • 123-acre estate
  • Max 22 guests

podere1384.it  ·  +39 0577 1722565  ·  Read more →

The medieval tower of Castello di Tornano rising above Chianti Classico vineyards near Gaiole
Gaiole in Chianti €€€

Castello di Tornano

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.

  • Tower suite
  • Estate wine
  • Pool
  • Vineyard views

castellotornano.it  ·  +39 0577 746067  ·  Read more →

The hilltop borgo of Borgo del Cabreo overlooking Sangiovese vines with Montefioralle in the distance, Greve in Chianti
Greve in Chianti €€€

Borgo del Cabreo

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 Super Tuscan blend first produced in 1982. Eleven rooms in the converted borgo overlook vine and cypress. There is no restaurant on site: guests dine at the sister property, Pietra del Cabreo, nearby. The new Cabreo winery opened in May 2026.

  • Panoramic pool
  • Estate wines
  • Dining at Pietra del Cabreo
  • Vineyard views
  • Montefioralle walks

borgodelcabreo.it  ·  +39 055 3985032  ·  Read more →

The salt-water infinity pool of Villa Le Barone looking over the Conca d’Oro vineyards of Panzano in Chianti
Panzano in Chianti €€€

Villa Le Barone

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.

  • Salt-water pool
  • Il Torchio restaurant
  • Tennis
  • Own olive oil
  • Historic house

villalebarone.com  ·  +39 055 85 26 21  ·  Read more →

The pool and vineyard panorama at Hotel Le Fontanelle near Pianella, Castelnuovo Berardenga
Pianella €€€

Hotel Le Fontanelle

Rural Hotel · Spa

A beautifully positioned rural hotel at Pianella, on the Sienese side of the zone, with an indoor heated pool, an outdoor pool, a full spa, and panoramic views across the vines and cypress hills of the Chianti Classico. The restaurant sources ingredients from the estate and from neighbouring farms. Ideal for those who want comfort and stillness in equal measure.

  • Indoor heated pool
  • Outdoor pool
  • Spa
  • Restaurant
  • Vineyard views

lefontanelle.com  ·  +39 0577 740194  ·  Read more →

La Darbia in Chianti at dusk: three stone farmhouses with lit windows among olive trees and cypresses, the pool in the foreground and vineyards on the hillside behind
Between Greve and Panzano €€€€

La Darbia in Chianti

Boutique hotel · Restored hilltop hamlet · Opened 2026

The newest address on this list opened in May 2026 on a fifteen-hectare estate between Greve and Panzano, twenty-five minutes from Florence. An avenue of pines leads up to three old stone farmhouses of an eleventh-century hamlet, now restored into seventeen suites and apartments, five of them designed for families. The estate keeps its olive groves, woodland and a broad lavender field where forty beehives produce the house honey.

  • 17 suites and apartments
  • Two pools
  • Spa area
  • Restaurant
  • Family suites
  • Lavender field & honey

chianti.ladarbia.com  ·  +39 351 498 4286  ·  Read more →

A bedroom at Pieve Aldina: linen bed and bench under old wooden beams, with herringbone terracotta floors and soft natural tones
Radda in Chianti €€€€

Pieve Aldina

Relais & Châteaux · Fontenille Collection · Former bishops’ residence

Pieve Aldina stands above the Chiantigiana near Radda, its buildings leaning against the Romanesque church of Santa Maria Novella. In the fifteenth and sixteenth centuries this was the summer residence of the bishops of Siena; in 2023 it opened as the first Italian house of the French Fontenille Collection, and it has been a member of Relais & Châteaux from the start. Twenty-two rooms and suites are spread across the old abbey house, the farm manager’s house and their outbuildings.

  • 22 rooms & suites
  • Outdoor pool
  • Spa with hammam
  • Le Rondini restaurant
  • Cooking classes
  • Pet friendly

pieve-aldina.fontenille-collection.com  ·  Read more →

A suite at COMO Castello Del Nero: frescoed walls and painted-marble door frames around a white bed, with a freestanding bath glimpsed in the next room
Tavarnelle Val di Pesa €€€€€

COMO Castello Del Nero

COMO Hotels · 12th-century castle · One MICHELIN Key

A twelfth-century castle on a 740-acre estate outside Tavarnelle, with Renaissance frescoes upstairs and interiors by the Milanese designer Paola Navone. It is COMO’s only hotel in Tuscany, and the MICHELIN Guide gave it one Key in 2024 and again in 2025. Beyond the castle, the estate holds Podere San Filippo, a farmhouse of twelve self-catering apartments, and Villa San Luigi, a five-bedroom villa with its own infinity pool.

  • COMO Shambhala spa
  • 25 m heated outdoor pool
  • La Torre (1 MICHELIN star)
  • Apartments & private villa
  • Tennis & padel
  • Shuttle to Florence and Siena

comohotels.com  ·  Read more →

The infinity pool at Castel Monastero, with the medieval hamlet and its bell tower rising above the gardens
Monastero d’Ombrone €€€€

Castel Monastero

Medieval castle hamlet · Spa Monasterii · MICHELIN-starred Contrada

Castel Monastero is first recorded in 1044, under the name of Sarna, and from 1050 is called Monastero after the nearby Berardenga abbey. Siena and Florence fought over it, and the Sienese Chigi Saracini family later made it their country house for hunting and the grape harvest. Restored as a resort, the castle and its hamlet now hold 68 rooms, suites and signature suites around a small piazza, plus Villa Lavanda for those who want a house of their own.

  • 68 rooms & suites
  • Spa Monasterii (c. 1,500 m²)
  • Contrada (1 MICHELIN star)
  • Cantina restaurant
  • Private villa
  • Family & dog friendly

castelmonastero.com  ·  +39 0577 570570  ·  Read more →

Aerial view of The Club House at Pievasciata at sunset: a long stone building with a cypress-lined drive, lawns and a golf green, hills fading into the distance
Pievasciata €€€€€

The Club House

Adults only · 15 rooms · MICHELIN-starred Il Visibìlio

The Club House opened in 2022 in a restored farmhouse near Pievasciata, at the end of a dirt road in the hills north of Siena. It is the quieter sibling of Hotel Le Fontanelle and the Vallepicciola winery, all three tied to the Bolfo family under the Fontanelle Estate name. Fifteen rooms and suites, adults only (teenagers from 14 are accepted), are done in classic Tuscan style; some suites have a private garden or a terrace over the valley.

  • 15 rooms & suites
  • Adults only (14+)
  • Panoramic outdoor pool
  • Spa (400+ m²)
  • Il Visibìlio (1 MICHELIN star)
  • Tennis & golf practice green

fontanellestate.com  ·  Read more →

Aerial view of Vignamaggio between Greve and Panzano: the rose-coloured Renaissance villa with its walled Italian gardens and pool, among vineyards and olive groves
Between Greve and Panzano €€€€

Vignamaggio

Historic wine estate · La Pensione in Panzano · Farmhouses

Vignamaggio is one of the great old names of the Greve valley: more than four hundred hectares between Greve and Panzano, a pink villa that was the Gherardini family’s home, and a letter of 1404 that is the first record of wine made here. A long restoration is still under way. The villa itself is closed for now, along with garden and cellar tours, but the rest of the estate is open again.

  • La Pensione hotel (21 rooms, Panzano)
  • Farmhouses & flats
  • Pool
  • Il Ristoro restaurant
  • Weddings at Il Borgo
  • Estate shop

vignamaggio.com  ·  Read more →

Aerial view of Borgo Scopeto near Vagliagli: the stone hamlet with its tower, pools and gardens, surrounded by olive groves, cypresses and vineyards
Vagliagli €€€€

Borgo Scopeto Wine & Country Relais

Medieval hamlet · Five-star relais · Views of Siena

Borgo Scopeto began as a fortified outpost of Siena; its name comes from the heather once cut here for brooms. Florence took it and left a stone Marzocco lion, still in the main garden. From the fourteenth to the nineteenth century the Sienese Sozzini family turned it into a castle and farming village, and in the 1990s Elisabetta Gnudi Angelini bought and restored it, with the Borgo Scopeto winery a few kilometres away.

  • 52 rooms, suites & villas
  • Two pools (one adults only)
  • Spa
  • La Tinaia restaurant
  • Views of Siena
  • Tennis

borgoscopetorelais.it  ·  +39 0577 320001  ·  Read more →

Smaller stays

The heated pool and terraced garden of Villa La Petraia, a historic villa in the heart of Panzano in Chianti
Panzano in Chianti €€€

Villa La Petraia

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.

  • Heated pool
  • Garden terrace
  • Cooking school
  • Wine experiences
  • Exclusive-use option

villalapetraia.com  ·  +39 333 9591881  ·  Read more →