Our top choices for Chianti Region hotels

Tenuta Decimo

San Gimignano

harman

￥12,225 total

includes taxes & fees

Jun 23 - Jun 24

Villa Sabolini

Colle di Val d'Elsa

DEANA

￥30,704 total

includes taxes & fees

Jun 21 - Jun 22

Agriturismo San Sano

Gaiole in Chianti

Shawn

￥22,002 total

includes taxes & fees

Jun 10 - Jun 11

Torre a Cona Wine Estate

Rignano sull'Arno

Jill

￥59,973 total

includes taxes & fees

Jul 2 - Jul 3

Castello Vicchiomaggio

Greve in Chianti

Tiffany

￥39,423 total

includes taxes & fees

Jun 10 - Jun 11

Salvadonica - Borgo del Chianti

San Casciano in Val di Pesa

Sterling

￥45,847 total

includes taxes & fees

Jun 8 - Jun 9

Hotel Il Viandante

Terranuova Bracciolini

Michelle

￥20,196 total

includes taxes & fees

Jul 5 - Jul 6

Castello di Tornano Wine Resort

Gaiole in Chianti

Austin

￥43,435 total

includes taxes & fees

Jun 23 - Jun 24

Palagina la cascina

Figline e Incisa Valdarno

Igor

￥20,652 total

includes taxes & fees

Jun 7 - Jun 8

Breakfast, lunch, dinner and brunch served

Villa San Lucchese

Poggibonsi

Carol

￥21,794 total

includes taxes & fees

Jun 21 - Jun 22

La Certosa di Pontignano

Castelnuovo Berardenga

Ken

￥27,129 total

includes taxes & fees

Jul 5 - Jul 6

2 restaurants; breakfast, lunch, and dinner served

Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

Jason

￥28,836 total

includes taxes & fees

Jun 21 - Jun 22

Hotel Colle Etrusco Salivolpi

Castellina in Chianti

Teodora

￥21,620 total

includes taxes & fees

Jun 28 - Jun 29

Borgo di Pietrafitta Relais

Castellina in Chianti

Simon

￥27,030 total

includes taxes & fees

Jun 18 - Jun 19

Villa il Poggiale - Dimora Storica

San Casciano in Val di Pesa

William

￥28,086 total

includes taxes & fees

Jun 28 - Jun 29

Hotel Casafrassi Wine Resort

Castellina in Chianti

Alex

￥11,255 total

includes taxes & fees

Jun 7 - Jun 8

Indoor pool, seasonal outdoor pool, sun loungers

Hotel Palazzo San niccolò & Spa

Radda in Chianti

gary

￥21,522 total

includes taxes & fees

Jun 18 - Jun 19

HOTEL LA FENICE

Reggello

"Place definitely had better times in terms of exterior looking, bedroom was ok ish in terms of size. really tiny shower, wifi stopped working through the night. breakfast was ok for a one night stop (cold cuts, vienosserie, boiled eggs, fruits, cake, cereal). possibility to safely store bicycle inside. Osteria next door is life saving for excellent food. the place is next to a very busy road, expect this when opening the window "

Ariel

￥15,199 total

includes taxes & fees

Jun 22 - Jun 23

Castello di Meleto

Gaiole in Chianti

Steven

￥42,507 total

includes taxes & fees

Jun 8 - Jun 9

Castello di Fonterutoli Wine Resort

Castellina in Chianti

Giancarlo

￥36,683 total

includes taxes & fees

Jun 15 - Jun 16

View all properties

Vacation Rentals in Chianti Region

Residence

Relais Villa Olmo

Impruneta

"We had an excellent stay, the staff is very friendly, stunning location and easy but windy road into Florence "

Aparthotel

Borgo Argenina

Gaiole in Chianti

"Such a beautiful place to stay! The cottage was amazing, very spacious and clean. The grounds themselves were picturesque, was well above our expectations and the host was very welcoming and accommodating."

Townhouse

Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

Villa di Sotto

Castelnuovo Berardenga

"Beautiful villa, very spacious, gorgeous property and great restaurant on the property to have a delicious meal. Staff very welcoming. Close to other main cities, like Siena, for day trips. We loved sitting by the pool, although it wasn’t heated, so too cold to use in April. We did love using the indoor heated pool and hot tub each day. We had a fabulous time and hope to go back someday! "

Residence

Castello Del Nero - Podere San Filippo

Barberino Tavarnelle

"Much nicer stay then the rooms at the Como"

Townhouse

B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes

San Casciano in Val di Pesa

"The beautiful place, very comfortable, the incredible attention, the breakfast felt like in Homewith a lot of love We hope to return one day"

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 Chianti 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

4.7/5 (16 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

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

Borgo Vescine

10/10 Excellent

"We enjoyed our stay immensely. The staff was very accommodating, especially with our two year old. The activities we did (movie night- included; dinner in the olive grove, truffle hunting, & a cooking class- paid) were all lovely experiences. We loved the property grounds."

Relais Vignale & Spa

4/10 Poor

"Honestly, I've had better stays at Motel 6. The staff were mostly indifferent about any of my requests. The room and facilities simply didn't measure up to the cost. The room was small - hardly room to open one suitcase, let alone two. No soap, or body wash dispenser in the shower. The only option was to drop the tiny hotel bar of soap on the floor, then hope you didn't kill yourself picking it up again. No Kleenex either. Yes, it's a small thing but at the price they charge... And the hotel is on a steep hillside, with stairs, stairs and more stairs. Not easy for anyone with even slight mobility issues. The one bright spot was the view from our room's terrace. The restaurant also has lovely views out over the Tuscan countryside. But overall ABSOLUTELY not worth the money."

Villa I Barronci Resort & Spa

8/10 Good

"Staff was friendly, property location is beautiful- The internet didn’t work in our room or side of the resort and the food was less than ideal, the food options were limited. After spending 10 days in other parts of Italy (sorento and Florence) and hotels, this was probably our least favorite."

Hotel Villa Ambrosina

10/10 Excellent

"This hotel is a gem! The staff is super friendly and they help a lot! Room was clean, shower is great, self parking is in front of the property. Located about 20 minutes from Florence in car. The breakfast was EXCELLENT! Coffee is great and the "Toscana mood" is all over. Thank for all your attention. If I could give 6 stars I would do it."