Chianti Region Hotels from from S$69

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Our top choices for Chianti Region hotels

A Casa Da Agata

A Casa Da Agata
Loro Ciuffenna
10.0 out of 10, Exceptional, (1)
Adventurous travellers will love the on-site hiking and biking trails at this scenic retreat. Enjoy complimentary perks including local cuisine breakfast, WiFi, and parking. Croce del Pratomagno and Soffena Abbey await nearby for cultural exploration.

"Our stay was aboslutely wonderful! The house and farm lies high up in the Tuscan hills and we were immersed in lush greenery with a river flowing nearby. Lorenzo was very welcoming and cooked us a delicious Tuscan dinner every night. We also loved his beautiful dog and two cats who made our stay extra nice! The room was sprakling clean and very cozy. "
United States
Carolina
The price is S$191
includes taxes & fees
27 Dec - 28 Dec
A Casa Da Agata

La Certosa di Pontignano

La Certosa di Pontignano
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (503)
Soak in Tuscany from the rooftop terrace at this charming Castelnuovo Berardenga retreat. The on-site restaurant serves Italian cuisine throughout the day, while the garden setting creates a peaceful atmosphere. Terra di Seta and free perks like WiFi, parking, and breakfast add value.

"Excellent place to stay even for the next time. "
Canada
Xuejie
The price is S$152
includes taxes & fees
26 Dec - 27 Dec
La Certosa di Pontignano

Hotel Palazzo San Lorenzo & SPA

Hotel Palazzo San Lorenzo & SPA
4.0 star property
Colle di Val d'Elsa
9.4 out of 10, Exceptional, (432)
This luxurious hotel offers indulgent spa services including massages and body wraps, plus a relaxing hot tub and sauna. Enjoy free breakfast at the café, then explore nearby Art in Colour and the Archaeological Museum, just minutes away.

"Beautiful hotel and spa. Excellent amenities and modern luxuries. "
United States
George
Hotel Palazzo San Lorenzo & SPA

VIESCA Suites & Villas – Il Borro Toscana

VIESCA Suites & Villas – Il Borro Toscana
Reggello
9.2 out of 10, Wonderful, (7)
Nestled in scenic Reggello, this farm stay offers deep-tissue massages and facials at the on-site spa. Enjoy convenient in-room refrigerators, an outdoor pool, and fitness centre. Close to Franciscan Monastery and Soffena Abbey with free WiFi and parking.

"A dream. Peaceful is the only word that comes to mind. "
United States
Margaux
The price is S$392
includes taxes & fees
2 Jan - 3 Jan, 2026
VIESCA Suites & Villas – Il Borro Toscana

Villa San Lucchese

Villa San Lucchese
4.0 star property
Poggibonsi
9.4 out of 10, Exceptional, (336)
Escape to this historic family-friendly hotel offering free breakfast and parking. Enjoy the seasonal outdoor pool and tennis courts, then unwind at the bar. Conveniently located near San Lucchese Convent and local Tuscan villages with train station access.

"Beautiful place Great service "
United States
patricia
Villa San Lucchese

Relais Della Rovere

Relais Della Rovere
4.0 star property
Colle di Val d'Elsa
9.0 out of 10, Wonderful, (243)
Elegant Italian hotel adjacent to golf course featuring outdoor pool and authentic cuisine at Il Cardinale restaurant. Enjoy free breakfast, WiFi and parking while exploring nearby Sentierelsa Trail and Piazza Arnolfo di Cambio, just minutes from Monteriggioni.

"Quietly located hotel with modern rooms and very good dinner option in the courtyard. Spacious pool to relax after long sightseeing days in the countryside."
Germany
Alexander
Relais Della Rovere

Hotel Toscana Ambassador

Hotel Toscana Ambassador
4.0 star property
Poggibonsi
8.2 out of 10, Very good, (317)
This business-friendly hotel offers 24-hour room service with easy access to Poggibonsi-San Gimignano Station. Unwind at the bar or coffee shop after exploring nearby attractions like Archeodromo di Poggibonsi and Poggio Imperiale Fortress.

"Wonderful breakfast. Good location!"
Canada
Karen
The price is S$92
includes taxes & fees
2 Jan - 3 Jan, 2026
Hotel Toscana Ambassador

B&B Poggiobonizio

B&B Poggiobonizio
Poggibonsi
9.2 out of 10, Wonderful, (62)
Wake up to continental breakfast at this welcoming Poggibonsi retreat. Just 4 minutes from the train station, with free WiFi and parking. Explore nearby Archeodromo di Poggibonsi and Fountain of Fate during your business or leisure stay.

"Simone is a really nice person, he help us a lot, very friendly, room was clean, breakfast was good. "
United States
Odalis
B&B Poggiobonizio

Hotel Ristorante Alcide

Hotel Ristorante Alcide
4.0 star property
Poggibonsi
8.0 out of 10, Very good, (478)
Savour regional specialities at Ristorante Alcide, just an 11-minute walk from Poggibonsi-San Gimignano Station. This hotel offers a welcoming bar, terrace, and room service, with Archeodromo di Poggibonsi and Fountain of Fate nearby.

"I highly recommended "
Canada
George
The price is S$69
includes taxes & fees
18 Jan - 19 Jan, 2026
Hotel Ristorante Alcide

Villa il Poggiale - Dimora Storica

Villa il Poggiale - Dimora Storica
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (145)
Escape to this historic villa with panoramic countryside views, an outdoor pool, and inviting coffee shop. Rejuvenate with hot stone massages while enjoying easy access to Florence attractions and free breakfast, WiFi, and parking.

"Wonderful stay."
United States
Nancy
The price is S$181
includes taxes & fees
8 Jan - 9 Jan, 2026
Villa il Poggiale - Dimora Storica

Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (71)
Surrounded by Chianti countryside near Piazza Matteotti, this charming affittacamere offers wine lovers a perfect retreat with an on-site winery, poolside bar, and hot tub. Indulge in free breakfast before exploring museum-rich Florence.

"The stay was great, and the staff were wonderful. "
United States
SYDNEY
Terre di Baccio

Relais Poggio Borgoni

Relais Poggio Borgoni
San Casciano in Val di Pesa
9.8 out of 10, Exceptional, (57)
Sip local wines at this charming countryside retreat between Florence and Chianti. The seasonal outdoor pool, hot tub, and Osteria del Poggio restaurant create a relaxing Italian escape. Free breakfast, WiFi and parking complement the attentive service.

"Very personal, kind & sympathatic Staff. The Place is gorgeous."
Switzerland
Nils
The price is S$176
includes taxes & fees
11 Jan - 12 Jan, 2026
Relais Poggio Borgoni

Torraccia di Chiusi

Torraccia di Chiusi
San Gimignano
10.0 out of 10, Exceptional, (97)
"A beautiful base for exploring Tuscany away from the crowds."
United States
Anthony
The price is S$277
includes taxes & fees
31 Dec - 1 Jan, 2026
Torraccia di Chiusi

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (97)
Enchanting affittacamere featuring a seasonal outdoor pool, relaxing massage services, and convenient bar. Located near Monastary of Sorelle Clarisse and Antinori nel Chianti Classico, with complimentary breakfast, WiFi, and parking for a perfect Italian countryside retreat.

"Great people, great location great service"
Canada
James
The price is S$205
includes taxes & fees
13 Jan - 14 Jan, 2026
Villa il Fedino

La Pensione di Vignamaggio

La Pensione di Vignamaggio
Panzano in Chianti
9.6 out of 10, Exceptional, (118)
Surrounded by Chianti countryside, this inviting pensione offers a seasonal outdoor pool and terrace for soaking up Tuscan sunshine. Enjoy complimentary breakfast before exploring nearby Church of Santa Maria Assunta. Comfortable rooms feature minibars and free WiFi.

"A beautiful location, fantastic view, close to wineries, little shops and local restaurants. "
Canada
Rob
La Pensione di Vignamaggio

Albergo Del Chianti

Albergo Del Chianti
3.0 star property
Greve in Chianti
8.6 out of 10, Excellent, (188)
Experience authentic Italian hospitality in the heart of Greve in Chianti. This hotel offers a relaxing seasonal outdoor pool, soothing hot tub, and convenient bar/lounge. Just steps from Piazza Matteotti and Wine Museum, enjoy Tuscan charm with modern comforts.

"Very friendly hotel, in a beautiful square. "
United Kingdom
Keith
Albergo Del Chianti

B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (82)
Perched in San Casciano in Val di Pesa, this charming B&B offers a refreshing seasonal pool and scenic rooftop terrace. Enjoy complimentary breakfast, WiFi, and parking while exploring nearby Florence American Cemetery and Memorial. The coffee shop and garden create a peaceful Tuscan retreat.

"It was a wonderful stay the bed was comfortable and the view was beautiful. "
United States
Ruben
The price is S$177
includes taxes & fees
26 Dec - 27 Dec
B&B La Fonte del Machiavelli

Castello di Meleto

Castello di Meleto
Gaiole in Chianti
8.8 out of 10, Excellent, (91)
Immerse yourself in authentic Tuscany at this historic castle estate. Enjoy wine tastings at the on-site winery, cool off in the seasonal outdoor pool, and dine at La Fornace di Meleto restaurant. Free WiFi and parking complement the beautiful garden and terrace settings.

"This Castle is AMAZING! Agatha and Victor so kind. I highly recommend this place. Wines are extremely wonderful. We really enjoy the staying."
United States
Karem
Castello di Meleto

Hotel La Vecchia Cartiera

Hotel La Vecchia Cartiera
3.0 star property
Colle di Val d'Elsa
8.4 out of 10, Very good, (203)
Immerse in Tuscan charm at this hotel featuring a restaurant serving local cuisine for lunch and dinner. Near Museo del Cristallo and Piazza Arnolfo di Cambio, with convenient amenities like free breakfast, WiFi, and room service. Unwind at the bar or terrace.

"The staff was very welcoming. Lovely quiet place. Close to a lot of good restaurants. "
Canada
Sheila
Hotel La Vecchia Cartiera

Hotel Albergo Italia

Hotel Albergo Italia
2.0 star property
Poggibonsi
8.4 out of 10, Very good, (46)
Built in 1880, this Poggibonsi accommodation sits just 3 minutes from the train station. Explore nearby Fountain of Fate and Archeodromo attractions, then unwind with drinks at the cosy bar after your adventures.

"When I arrived the hotel was closed. I have had to sleep in the car"
United States
Martin
Hotel Albergo Italia
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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