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

Next weekend
In two weeks

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$191
includes taxes & fees
28 Dec - 29 Dec
A Casa Da Agata

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$93
includes taxes & fees
2 Jan - 3 Jan, 2026
Hotel Toscana Ambassador

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$71
includes taxes & fees
4 Jan - 5 Jan, 2026
Hotel Ristorante Alcide

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

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

Hotel Villa San Giorgio

Hotel Villa San Giorgio
3.0 star property
Poggibonsi
9.0 out of 10, Wonderful, (105)
Immerse in Poggibonsi's charm at this welcoming hotel featuring poolside dining at Villa Aurora restaurant. Enjoy the hot tub and children's pool after exploring nearby Castello di Monsanto. Just a 12-minute drive from the train station for Tuscan adventures.

"Loved the breakfast amazing !!! Such a beautiful place woujd love to go in summer and lay by the pool "
Australia
Kylie
The price is S$83
includes taxes & fees
28 Dec - 29 Dec
Hotel Villa San Giorgio

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$183
includes taxes & fees
28 Dec - 29 Dec
La Certosa di Pontignano

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

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$391
includes taxes & fees
2 Jan - 3 Jan, 2026
VIESCA Suites & Villas – Il Borro Toscana

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$176
includes taxes & fees
11 Jan - 12 Jan, 2026
Relais Poggio Borgoni

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
28 Dec - 29 Dec
B&B La Fonte del Machiavelli

Palazzo Tiglio - A Small Luxury Hotels of the World

Palazzo Tiglio - A Small Luxury Hotels of the World
Bucine
10.0 out of 10, Exceptional, (3)
Set in Bucine, this luxurious retreat offers a refreshing outdoor pool and peaceful garden terrace. Near historic Civitella Longobard Castle, guests enjoy complimentary WiFi and parking while exploring Tuscan treasures, with a café and lounge for relaxation.

"We found it to be a charming, immaculate, upscale retreat with a hilltop view of the beautiful countryside. We were given personalized attention and many unexpected fine touches, like fresh fruit in the room. Highly recommend."
United States
David
The price is S$501
includes taxes & fees
29 Dec - 30 Dec
Palazzo Tiglio - A Small Luxury Hotels of the World

Le Lappe

Le Lappe
Cavriglia
9.6 out of 10, Exceptional, (32)
Immerse yourself in Cavriglia's charm at this countryside retreat featuring an outdoor pool, hot tub, and rejuvenating sports massages. Savour Italian specialities at Giardino d'Inverno restaurant before exploring nearby Le Miccine attractions with convenient free parking and WiFi.

"Beautiful property in countryside Tuscany region ideal to stay for 2-7 days."
Canada
shrirang
Le Lappe

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$195
includes taxes & fees
13 Jan - 14 Jan, 2026
Villa il Fedino

Hotel Il Castello

Hotel Il Castello
Certaldo Alto
9.6 out of 10, Exceptional, (7)
Positioned near Certaldo Station, this hotel offers complimentary breakfast and WiFi while placing you moments from Museum of Sacred Art and Casa del Boccaccio. After sightseeing, unwind at the inviting bar.

"What a great little hotel! The town is rather small and not much shops like San Gimignano, but this hotel is clean, rooms are roomy and the garden dining is out of this world. Beautiful with views of the sunset and amazing food. One of my favorite. The town has several restaurants too and some good museums. "
United States
Thomas
The price is S$208
includes taxes & fees
2 Jan - 3 Jan, 2026
Hotel Il Castello

Agriturismo Nerbona

Agriturismo Nerbona
Colle di Val d'Elsa
9.6 out of 10, Exceptional, (18)
Discover rural Tuscan charm at this countryside retreat with a refreshing seasonal pool, free bike rentals, and volleyball court. Perfectly positioned near Archaeological Museum and Il Palagio Winery, with convenient parking for day trips.

"Very nice place"
United States
JULISSA
The price is S$141
includes taxes & fees
29 Dec - 30 Dec
Agriturismo Nerbona

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
29 Dec - 30 Dec
Torraccia di Chiusi

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

Hotel La Magione

Hotel La Magione
Poggibonsi
6.0 out of 10, (3)
"La vista sulle colline è bella,le camere pulite e il personale accogliente "
Italy
Gerardo
The price is S$80
includes taxes & fees
18 Jan - 19 Jan, 2026
Hotel La Magione
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