Our top choices for Chianti Region hotels

A Casa Da Agata

Loro Ciuffenna

Soak in breathtaking views from the rooftop terrace at this charming B&B in Loro Ciuffenna.

Carolina

￥23,244 total

includes taxes & fees

Jan 25 - Jan 26

Hotel Toscana Ambassador

Poggibonsi

Located near the train station, enjoy relaxing at the bar and terrace in Poggibonsi.

Karen

Hotel Ristorante Alcide

Poggibonsi

Convenient train station hotel with regional cuisine and charming terrace.

George

￥9,025 total

includes taxes & fees

Feb 15 - Feb 16

La Certosa di Pontignano

Castelnuovo Berardenga

Tuscan countryside B&B with rooftop terrace views and Italian dining.

Xuejie

￥19,632 total

includes taxes & fees

Feb 15 - Feb 16

B&B Poggiobonizio

Poggibonsi

Charming B&B near Poggibonsi-San Gimignano Station with complimentary perks.

Odalis

Villa I Barronci Resort & Spa

San Casciano in Val di Pesa

Experience Tuscany's scenic countryside from a luxurious spa retreat.

Luis

￥15,109 total

includes taxes & fees

Jan 25 - Jan 26

Salvadonica - Borgo del Chianti

San Casciano in Val di Pesa

John

￥17,846 total

includes taxes & fees

Feb 22 - Feb 23

Couples treatment rooms, sauna, hot tub, Turkish bath, body treatments

Hotel Palazzo San Lorenzo & SPA

Colle di Val d'Elsa

Experience luxury in the heart of Colle di Val d'Elsa with spa treatments and gourmet café.

George

Villa il Poggiale - Dimora Storica

San Casciano in Val di Pesa

Tranquil retreat in Val di Pesa offers rooftop terrace and peaceful ambiance.

Nancy

￥19,280 total

includes taxes & fees

Feb 8 - Feb 9

Palazzo Pacini

Colle di Val d'Elsa

Tuscan residence next to a golf course with its own winery and terrace.

George

￥20,166 total

includes taxes & fees

Jan 25 - Jan 26

Hotel Albergo Italia

Poggibonsi

Historic Italian hotel offers quick station access and a charming bar lounge.

Martin

Relais Poggio Borgoni

San Casciano in Val di Pesa

Serene Tuscan farmhouse in Chianti with pool, winery, and on-site dining.

Samuel

￥21,771 total

includes taxes & fees

Feb 23 - Feb 24

Hotel Villa San Giorgio

Poggibonsi

Tranquil Tuscan retreat with Italian cuisine by the seasonal outdoor pool.

Kylie

￥10,321 total

includes taxes & fees

Jan 25 - Jan 26

B&B La Fonte del Machiavelli

San Casciano in Val di Pesa

Rooftop terrace views with seasonal pool in Tuscan countryside.

Ruben

￥21,310 total

includes taxes & fees

Feb 12 - Feb 13

Villa il Fedino

San Casciano in Val di Pesa

Rooftop terrace with scenic Tuscan views in San Casciano in Val di Pesa.

James

￥26,012 total

includes taxes & fees

Feb 3 - Feb 4

Torraccia di Chiusi

San Gimignano

Anthony

￥33,738 total

includes taxes & fees

Feb 13 - Feb 14

Hotel La Vecchia Cartiera

Colle di Val d'Elsa

Charming Tuscan retreat near Colle di Val d'Elsa with local cuisine and terrace.

Sheila

Terre di Baccio

Greve in Chianti

Escape to Tuscany with vineyard views from this winery hotel with a rooftop terrace.

SYDNEY

Hotel Torciano Vecchio Asilo

San Gimignano

Necola

Castello di Meleto

Gaiole in Chianti

Luxurious Tuscan castle with winery and seasonal pool in Gaiole in Chianti.

Anna

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Vacation Rentals in Chianti Region

Townhouse

Villa Cassia di Baccano

Loro Ciuffenna

"The staff were great and the villa was amazing"

Townhouse

Rocca di Castagnoli

Gaiole in Chianti

"It was wonderful to stay in a castle in Tuscany no less Every person we met was attentive and kind We were staying near friends and didn’t hang around the grounds much or use the pool but everything seemed well kept It’s really a place to retreat to eat at and sleep at which served our purpose well "

Apartment

Poggio Cennina Resort

Bucine

"The resort is in the most stunning setting. The pool is fantastic. The accommodation is comfortable and has everything you need. The staff were very friendly and helpful. We would highly recommend and would return for another stay."

Townhouse

L' Eroico

Gaiole in Chianti

"Monica was the friendliest most enthusiastic host we’ve stayed with. Everything from her greeting to the amazing breakfast was perfect. She does a lot of baking, so the breakfast was really a treat and you could also get eggs cooked in various ways. The room was a little small but very comfortable. Parking was on the street, but it was fairly close and easy."

Townhouse

Seasonal outdoor pool, pool umbrellas, sun loungers

Farmhouse in Castiglion Fibocchi

Castiglion Fibocchi

"Marisol was so welcoming and helpful. Beautiful apartment and scenery. Would definitely recommend "

Residence

Chianti Village Morrocco

Barberino Tavarnelle

"Spacious room in large resort style complex, set up as fully self contained with kitchen and dining furniture. Peaceful location with lovely views. Very pleasant staff and exceptional breakfast. "

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Stay near popular Mediterranean Region attractions

A woman on a spiral stairway, part of the modern architecture at Antinori Winery Nel Chianti Classico, San Casciano in Val di Pesa, Tuscany, Italy.

Antinori nel Chianti Classico

4.4/5 (7 reviews)

You can enjoy a tasting or tour at Antinori nel Chianti Classico during your travels to Bargino. Check out the churches and wineries in this walkable area.

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Night view of the architecture of the small town of Florence, Shanghai

The Mall Luxury Outlet

4.3/5 (336 reviews)

During your visit to Leccio, you can search for that perfect souvenir at The Mall Luxury Outlet. Discover the acclaimed art scene and churches in this walkable area.

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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.

See all hotels in Chianti Region

Top Chianti Region Hotel Reviews

Villa Casagrande Resort & SPA

10/10 Excellent

"Always beautiful when I stay here, staff are helpful and every room clean and tidy "

Castello Vicchiomaggio

10/10 Excellent

"This beautiful property stole our hearts back in 2019, when my now-wife first visited this magical place. Six years later, we returned — this time to celebrate our wedding reception after tying the knot a few months earlier. From start to finish, everything was beyond wonderful. A special mention to Sandra, the amazing coordinator who made everything run so smoothly, and her fantastic team — Delfina and the lovely lady (whose name, unfortunately, I’ve forgotten) who graciously welcomed and ushered our guests upon arrival. Every detail was handled with care and professionalism. The food and Chianti wines during our celebration were absolutely exceptional — truly a highlight that everyone still talks about! The breakfast and dinner staff were attentive, kind, and ensured everything was perfect throughout our stay. Our rooms were clean, comfortable, and beautifully maintained, with housekeeping doing a fantastic job. We also had the privilege of meeting Mr. John Matta, the owner — such a gracious and inspiring man who leads an extraordinary team. All of our guests loved their stay, and we left with hearts full of joy and gratitude. We can’t wait to come back again — hopefully for our anniversary next time."