Our top choices for Chianti Region hotels

Salvadonica - Borgo del Chianti

San Casciano in Val di Pesa

John

￥18,761 total

includes taxes & fees

Feb 17 - Feb 18

Villa Cassia di Baccano

Loro Ciuffenna

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

Ralphvincent

￥20,814 total

includes taxes & fees

Jan 26 - Jan 27

La Certosa di Pontignano

Castelnuovo Berardenga

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

Xuejie

￥19,626 total

includes taxes & fees

Feb 14 - Feb 15

Castello di Meleto

Gaiole in Chianti

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

Anna

Torraccia di Chiusi

San Gimignano

Anthony

￥33,732 total

includes taxes & fees

Feb 13 - Feb 14

Hotel Il Viandante

Terranuova Bracciolini

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

Michelle

￥20,160 total

includes taxes & fees

Feb 15 - Feb 16

Villa il Fedino

San Casciano in Val di Pesa

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

James

￥25,726 total

includes taxes & fees

Jan 26 - Jan 27

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

￥16,773 total

includes taxes & fees

Feb 21 - Feb 22

Antica Pieve B&B

Barberino Tavarnelle

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

Jessica

￥20,067 total

includes taxes & fees

Feb 21 - Feb 22

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

￥19,667 total

includes taxes & fees

Feb 16 - Feb 17

Hotel Borgo San Luigi

Monteriggioni

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

Allyson

Exclusive Studio Suite, 1 Bedroom, Hot Tub, Garden View | Premium bedding, down comforters, in-room safe, desk

Casa di Palaia

Greve in Chianti

Experience Tuscan charm from a rooftop terrace and seasonal outdoor pool.

Eli

￥15,650 total

includes taxes & fees

Jan 22 - Jan 23

Hotel Borgo di Cortefreda Relais

Barberino Tavarnelle

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

Michelle

￥17,675 total

includes taxes & fees

Feb 9 - Feb 10

Agriturismo La Posta Reale

Castiglion Fibocchi

Enjoy the on-site winery and authentic Italian cuisine in a tranquil farm setting.

Michael

Villa I Barronci Resort & Spa

San Casciano in Val di Pesa

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

Luis

￥16,846 total

includes taxes & fees

Jan 28 - Jan 29

Torrebianca Tuscany

Rignano sull'Arno

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

christine

￥15,154 total

includes taxes & fees

Feb 1 - Feb 2

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

￥17,843 total

includes taxes & fees

Feb 10 - Feb 11

L' Eroico

Gaiole in Chianti

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

Perry

Dimora Casa Eugenia

Loro Ciuffenna

Hike lush trails and enjoy rooftop vistas at a charming family guesthouse in Loro Ciuffenna.

Shannon

Agriturismo Montemagni di Sopra

Greve in Chianti

Tuscan farmhouse escape with vineyard views and rooftop terrace in Chianti.

Rachel

￥17,306 total

includes taxes & fees

Jan 22 - Jan 23

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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

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."

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

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 "

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. "

Residence

Panoramic Apartment, 4 Bedrooms (Refrigerator,Galleria) | Living area

Castello di Montegufoni

Montespertoli

"This was a stunning castle to stay in. The frescoed ceilings were gorgeous. Loved every minute that we were there. The staff were wonderful. The only thing i would recommend is to add a vending machine and maybe to offer pastries in thr morning. "

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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."