Our top choices for Chianti Region hotels

Salvadonica - Borgo del Chianti

San Casciano in Val di Pesa

John

￥17,846 total

includes taxes & fees

Feb 22 - Feb 23

Hotel Borgo di Cortefreda Relais

Barberino Tavarnelle

Tranquil Tuscan retreat with rooftop terrace views and indulgent spa services.

Michelle

￥17,678 total

includes taxes & fees

Feb 8 - Feb 9

Villa Cassia di Baccano

Loro Ciuffenna

Tranquil Tuscan retreat with poolside dining and spa treatments in Loro Ciuffenna.

Ralphvincent

￥26,609 total

includes taxes & fees

Jan 28 - Jan 29

Torraccia di Chiusi

San Gimignano

Anthony

￥33,738 total

includes taxes & fees

Feb 13 - Feb 14

Castello di Meleto

Gaiole in Chianti

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

Anna

2 restaurants, breakfast, lunch, dinner served; Italian cuisine

Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

Experience Tuscan elegance at this historic spa resort with indoor and outdoor pools.

Claire

￥17,716 total

includes taxes & fees

Feb 10 - Feb 11

Hotel Il Viandante

Terranuova Bracciolini

Experience a tranquil retreat in Tuscany with easy access to local attractions.

Michelle

￥20,017 total

includes taxes & fees

Feb 15 - Feb 16

Il Borro - Relais & Châteaux

Loro Ciuffenna

Unwind at this Tuscan gem with a winery, pool, and two inviting restaurants.

Ian

￥70,853 total

includes taxes & fees

Feb 25 - Feb 26

Relais Poggio Borgoni

San Casciano in Val di Pesa

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

Samuel

￥19,517 total

includes taxes & fees

Feb 25 - Feb 26

Antica Pieve B&B

Barberino Tavarnelle

Escape to the peaceful Tuscan countryside in this charming Barberino B&B.

Jessica

￥20,073 total

includes taxes & fees

Feb 15 - Feb 16

Hotel Borgo San Luigi

Monteriggioni

Experience Tuscan countryside views from the rooftop terrace with seasonal pool.

Allyson

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 14 - Feb 15

Indoor pool, seasonal outdoor pool, sun loungers

Hotel Palazzo San niccolò & Spa

Radda in Chianti

Relax in Tuscany with hot stone massages and wine country exploration.

Dee

￥18,887 total

includes taxes & fees

Feb 2 - Feb 3

Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas

Agriturismo Nerbona

Colle di Val d'Elsa

Tuscan farm stay with seasonal outdoor pool and mountain biking trails nearby.

JULISSA

￥16,776 total

includes taxes & fees

Feb 21 - Feb 22

Torrebianca Tuscany

Rignano sull'Arno

Tuscan retreat with free breakfast and nearby luxury shopping at The Mall outlet.

christine

￥15,156 total

includes taxes & fees

Feb 8 - Feb 9

Hotel Colle Etrusco Salivolpi

Castellina in Chianti

Scott

Villa il Fedino

San Casciano in Val di Pesa

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

James

￥25,002 total

includes taxes & fees

Jan 27 - Jan 28

Villa I Barronci Resort & Spa

San Casciano in Val di Pesa

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

Luis

￥13,518 total

includes taxes & fees

Jan 27 - Jan 28

Chiantirooms Guesthouse

Greve in Chianti

Perfect countryside escape with a scenic rooftop terrace in Greve in Chianti.

Pasquale

L' Eroico

Gaiole in Chianti

Experience the tranquil heart of Chianti with a stay in charming Gaiole surroundings.

Perry

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Vacation Rentals in Chianti Region

Townhouse

Villa il Fedino

San Casciano in Val di Pesa

"Great people, great location great service"

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

Rocca Palazzaccio

Impruneta

"A lovely stay at this property with our 2 year old.The apartment had everything we needed and communication with the host was very good There are steep hills to access the property by car or foot so bear that in mind but we managed fine with a pram and a car its just worth noting Handy to have laundry facilities on site aswell. There is a coop just a few minutes down the road Lovely views and a clean pool which was perfect for our little one to use and toys there that he could play in the...

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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."