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Our top choices for Chianti Region hotels

A spacious interior with high arched ceilings, stone walls, and a central round mirror reflecting the room. Tables and chairs are arranged for dining or socializing.

1. COMO Castello Del Nero

Tavarnelle Val di Pesa

Nawaf

￥127,412 total

includes taxes & fees

Nov 27 - Nov 28

A building with a stone facade, a central arched doorway, and a window with a decorative frame.

2. Dievole Wine Resort

Castelnuovo Berardenga

Magdalena

￥47,457 total

includes taxes & fees

Nov 20 - Nov 21

A candle on a tray with corks, a glass with a drink and an orange slice, and a table with chairs in an outdoor setting with arches in the background.

3. La Certosa di Pontignano - Place of Charme

Castelnuovo Berardenga

Rodolfo

￥12,768 total

includes taxes & fees

Dec 13 - Dec 14

A dining area with a table and chairs, a view of a landscape through an arched window, and a large umbrella providing shade.

4. Chapter Chianti, a Member of Design Hotels

Cavriglia

Carolina

￥67,339 total

includes taxes & fees

Nov 14 - Nov 15

A spa area with stone walls, a white massage chair, and a potted plant.

5. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Elizabeth

￥19,553 total

includes taxes & fees

Dec 1 - Dec 2

A swimming pool, steps, and a grassy area with umbrellas.

6. Hotel Palazzo San Lorenzo & SPA

Colle di Val d'Elsa

Kerry

￥18,657 total

includes taxes & fees

Nov 15 - Nov 16

A rustic cellar with brick walls, wooden barrels, and a stone ceiling. There is a wooden table with a wine bottle and glasses, and a television mounted on the wall.

7. Belvedere di San Leonino

Castellina in Chianti

Kevork

￥19,746 total

includes taxes & fees

Nov 14 - Nov 15

A spa area with a stone ceiling, a pool, and two sun loungers.

8. Hotel Palazzo San niccolò & Spa

Radda in Chianti

Afeefa

￥13,745 total

includes taxes & fees

Dec 10 - Dec 11

A narrow stone pathway leading to a rustic building with a wooden door and a window.

9. Castello di Fonterutoli Wine Resort

Castellina in Chianti

Saion

￥26,948 total

includes taxes & fees

Nov 13 - Nov 14

An outdoor patio with tables and chairs, a pergola structure, and a stone building in the background.

10. Tenuta CorteDomina

Radda in Chianti

piyanut

￥41,617 total

includes taxes & fees

Nov 14 - Nov 15

A courtyard with stone flooring, arched walkways, and a central fountain.

11. Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

Ana

￥15,761 total

includes taxes & fees

Dec 13 - Dec 14

A pool with a pink flamingo float, surrounded by lounge chairs and a stone deck.

12. La Pensione di Vignamaggio

Panzano in Chianti

Jacob

￥26,251 total

includes taxes & fees

Nov 13 - Nov 14

A person sitting by a swimming pool with a stone building in the background.

13. Hotel Borgo di Cortefreda Relais - Place of Charme

Tavarnelle Val di Pesa

Rahul

￥15,710 total

includes taxes & fees

Nov 27 - Nov 28

An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

14. Palazzo Pacini

Colle di Val d'Elsa

John

￥20,643 total

includes taxes & fees

Dec 12 - Dec 13

A historic stone building with multiple levels, surrounded by lush greenery and yellow flowering plants.

15. Castello La Leccia

Castellina in Chianti

Susan

￥40,061 total

includes taxes & fees

Nov 13 - Nov 14

A covered outdoor seating area with a wooden door, wicker chairs, and potted plants.

16. Borgo Vescine

Radda in Chianti

Natalie

￥76,977 total

includes taxes & fees

Nov 26 - Nov 27

A person sitting in a corner of a room with tiled walls and a bench.

17. Hotel Il Piccolo Castello

Monteriggioni

Frank

￥20,699 total

includes taxes & fees

Nov 15 - Nov 16

A spacious lobby with a reception desk, seating area, and a large vase.

18. Hotel Valdarno

Montevarchi

Emmanuel

￥19,698 total

includes taxes & fees

Nov 14 - Nov 15

A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

19. Terre di Baccio

Greve in Chianti

Gage

￥45,949 total

includes taxes & fees

Nov 15 - Nov 16

A modern bedroom with a wooden floor, a bed with a headboard, a window with curtains, and a shower area with a towel rack.

20. Park Hotel Chianti

Tavarnelle Val di Pesa

Manuel

￥9,615 total

includes taxes & fees

Nov 13 - Nov 14

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Vacation Rentals in Chianti Region

Residence

A stone building with a courtyard, a swimming pool, and vineyard fields in the background.

Riserva di Fizzano Residence

Castellina in Chianti

"Great place to stay in Tuscany! Very nice breakfast also!"

Townhouse

A stone building with a tiled roof, multiple windows, and a prominent tower.

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 "

Residence

A swimming pool with a stone fountain, surrounded by a grassy area and trees.

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

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

San Casciano in Val di Pesa

"Me and my girlfriend really did enjoy this property. Both host were very friendly and welcoming to us. We both did enjoy the feel at Home environment. We would definitely come back here on a future trip. Big shout out to the host for the wonderful cook meals. Great to know a bit about them as well."

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Stay near popular Chianti Region attractions

A spiral staircase with a person standing on it.

Antinori nel Chianti Classico

9.4/10 (16 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.

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

Terraced vineyards on a hillside, a small village, and rolling green hills.

Top Chianti Region Hotel Reviews

Il Borro - Relais & Châteaux

10/10 Excellent

"Excellent unique property with top notch service, attention and experiences. The food and staff at Osteria Il Borro were exceptional!"

Borgo Vescine

10/10 Excellent

"There are no words to describe our experience at this incredibly beautiful and wonderful charming several century old village resort in Chianti. It was everything you imagined Italy to be in wine country. Probably one of my favorite places I have ever stayed at, and I’ve stayed at hundreds of of places around the world. The staff was wonderful, the accommodations were just super cool. It was once a village dating back over 100+ years. It was truly remarkable that the owner discovered it and restored it, creating a truly wonderful experience and beautiful Tuscany. We definitely will stay here every time we go to Tuscany in the future. This is a must-stay place!"

Hu Norcenni Girasole Village

10/10 Excellent

"My family and I had such a great time. Such a kid friendly place and at check in they even had a little playground while you waiting and gave the kids bubbles. So great to be in nature and all of the amenities were lovely. The waterparks that were padded on the ground were genius and we did a family wine tasting which was such a lovely memory. Our stay was so nice with the deck and the grocery store is so affordable for dinners in. Love love love! My toddler played all day and there were so many times we got to relax because they had everything that we wanted or needed right on property."