Chianti Region Hotels from from S$71

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Star rating

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$190
includes taxes & fees
4 Jan - 5 Jan
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$170
includes taxes & fees
5 Jan - 6 Jan
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, (433)
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$390
includes taxes & fees
5 Jan - 6 Jan
VIESCA Suites & Villas – Il Borro Toscana

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
11 Jan - 12 Jan
Villa il Poggiale - Dimora Storica

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 Ristorante Alcide

Hotel Ristorante Alcide
4.0 star property
Poggibonsi
8.0 out of 10, Very good, (480)
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$71
includes taxes & fees
4 Jan - 5 Jan
Hotel Ristorante Alcide

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$95
includes taxes & fees
4 Jan - 5 Jan
Hotel Toscana Ambassador

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

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

Relais Poggio Borgoni

Relais Poggio Borgoni
San Casciano in Val di Pesa
9.8 out of 10, Exceptional, (58)
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$168
includes taxes & fees
11 Jan - 12 Jan
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$276
includes taxes & fees
4 Jan - 5 Jan
Torraccia di Chiusi

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

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$227
includes taxes & fees
13 Jan - 14 Jan
Villa il Fedino

Agriturismo Villa Ulivello in Chianti

Agriturismo Villa Ulivello in Chianti
Greve in Chianti
10.0 out of 10, Exceptional, (11)
"This place os amazing, great service, food and the apartment we picked had everything we needed. The crew made us feel at home since we walked in!"
United States
Leandro
The price is S$172
includes taxes & fees
8 Jan - 9 Jan
Agriturismo Villa Ulivello in Chianti

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

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$176
includes taxes & fees
2 Feb - 3 Feb
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 Torciano Vecchio Asilo

Hotel Torciano Vecchio Asilo
San Gimignano
9.6 out of 10, Exceptional, (54)
"Great boutique hotel in the middle of Tuscany. Wonderful views. The staff was very friendly and accommodating. We really loved the complimentary wine tasting at their nearby winery! We only wish their rooftop deck would’ve been open for even better views. The hotel and winery are family owned and it’s very clear that they value every guest!"
United States
Necola
Hotel Torciano Vecchio Asilo
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.

Holiday Rentals in Chianti Region

Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Mediterranean Region attractions

Learn more about Chianti Region

Take a sightseeing trip of Tuscany's renowned wine region and visit its vineyards, wineries, ancient churches, castles and hilltop villages.

Chianti Region featuring farmland

Top Chianti Region Hotel Reviews

More cheap stays in Chianti Region

Hotels in Chianti Region with star rating

Explore a world of travel with Expedia