Our top choices for Chianti Region hotels

Villa Sabolini

Colle di Val d'Elsa

Tranquil countryside retreat with panoramic views and poolside relaxation.

Amit

￥17,708 total

includes taxes & fees

Mar 1 - Mar 2

Castello La Leccia

Castellina in Chianti

Serene vineyard escape with mountain views and Tuscan spa treatments.

haluk

￥30,935 total

includes taxes & fees

Mar 12 - Mar 13

La Certosa di Pontignano

Castelnuovo Berardenga

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

Xuejie

￥17,028 total

includes taxes & fees

Mar 2 - Mar 3

Castello Vicchiomaggio

Greve in Chianti

Experience a charming Tuscan wine estate with seasonal pool and regional cuisine.

Cheyenne

￥30,010 total

includes taxes & fees

Mar 13 - Mar 14

Castello di Tornano Wine Resort

Gaiole in Chianti

Escape to a Tuscan wine paradise with poolside views and tennis courts nearby.

Matthew

Salvadonica - Borgo del Chianti

San Casciano in Val di Pesa

Paula

￥17,634 total

includes taxes & fees

Feb 23 - Feb 24

Villa il Poggiale - Dimora Storica

San Casciano in Val di Pesa

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

Nancy

￥18,984 total

includes taxes & fees

Feb 22 - Feb 23

Capanna 1826

San Gimignano

Scenic wine retreat in Tuscany with daily gourmet breakfast and lush gardens.

Jim

Castello di Fonterutoli Wine Resort

Castellina in Chianti

Elegant wine resort in Chianti offers Italian cuisine and peaceful countryside setting.

Matthew

Borgo Del Cabreo

Greve in Chianti

Jeffrey

La pietra del cabreo

Greve in Chianti

Enchanting Chianti stay with a seasonal pool, vineyard views, and gourmet dining.

Stephen R

Il Borro - Relais & Châteaux

Loro Ciuffenna

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

Ian

￥70,015 total

includes taxes & fees

Feb 24 - Feb 25

Hotel Borgo di Cortefreda Relais

Barberino Tavarnelle

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

Michelle

￥19,471 total

includes taxes & fees

Feb 15 - Feb 16

Castello Di Montemasso

Greve in Chianti

Experience the charm of Tuscany at a historic castle in Greve in Chianti.

Kathleen

￥19,764 total

includes taxes & fees

Mar 1 - Mar 2

Corte di Valle Wine and Resort

Greve in Chianti

Wake up in the heart of Tuscany and sip wine at an estate with pool and terrace.

Eddie

Hotel Borgo San Luigi

Monteriggioni

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

Allyson

Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

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

Claire

￥19,134 total

includes taxes & fees

Mar 1 - Mar 2

Castello di Meleto

Gaiole in Chianti

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

Anna

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

￥16,250 total

includes taxes & fees

Mar 12 - Mar 13

Borgo di Pietrafitta Relais

Castellina in Chianti

Experience Tuscan countryside charm at this winery retreat with outdoor pool.

Nelson

￥16,559 total

includes taxes & fees

Mar 16 - Mar 17

View all properties

Vacation Rentals in Chianti Region

Vacation Home

Deluxe Apartment | Premium bedding, down comforters, in-room safe, desk

Borgo Argiano

Castelnuovo Berardenga

"Very comfortable stay. "

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

Seasonal outdoor pool, pool umbrellas, sun loungers

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...

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

Farmhouse in Castiglion Fibocchi

Castiglion Fibocchi

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

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."

See all vacation rentals

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

Sign in

Sign up, it's free

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 stunning cathedral and wineries in this walkable area.

See properties

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.

See properties

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

Hotel Palazzo San Lorenzo & SPA

10/10 Excellent

"Very good place, clean, good service, great food, the rooms were amazing."

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."