Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Chianti Region hotels

An aerial view of a historic estate with multiple buildings, a swimming pool, and terraced vineyards.

1. COMO Castello Del Nero

Tavarnelle Val di Pesa

Nawaf

￥127,451 total

includes taxes & fees

Nov 27 - Nov 28

A cozy living room with a sofa, a coffee table, and a view of greenery through large windows.

2. Dievole Wine Resort

Castelnuovo Berardenga

Magdalena

￥47,472 total

includes taxes & fees

Nov 20 - Nov 21

A bedroom with a canopy bed, a bedside table, a chair, a potted plant, and a large mirror.

3. Chapter Chianti, a Member of Design Hotels

Cavriglia

Carolina

￥47,877 total

includes taxes & fees

Nov 12 - Nov 13

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

4. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Elizabeth

￥19,560 total

includes taxes & fees

Dec 1 - Dec 2

A stone building with ivy-covered walls, a stone pathway, and a garden with flowers.

5. Belvedere di San Leonino

Castellina in Chianti

Kevork

￥19,752 total

includes taxes & fees

Nov 12 - Nov 13

An aerial view of a historic building complex with a central courtyard, surrounded by vineyards and greenery.

6. La Certosa di Pontignano - Place of Charme

Castelnuovo Berardenga

Rodolfo

￥13,548 total

includes taxes & fees

Nov 16 - Nov 17

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

7. Hotel Palazzo San Lorenzo & SPA

Colle di Val d'Elsa

Kerry

￥18,662 total

includes taxes & fees

Nov 15 - Nov 16

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

8. Hotel Palazzo San niccolò & Spa

Radda in Chianti

Afeefa

￥13,752 total

includes taxes & fees

Dec 10 - Dec 11

A stone building with a tiled roof, green shutters, and a small staircase leading to a door.

9. Castello di Fonterutoli Wine Resort

Castellina in Chianti

Micaela

￥26,958 total

includes taxes & fees

Nov 12 - Nov 13

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

10. Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

Ana

￥20,343 total

includes taxes & fees

Nov 30 - Dec 1

A rustic stone wall with a window, a potted plant, a bust sculpture, and a table with a magazine.

11. Tenuta CorteDomina

Radda in Chianti

piyanut

￥38,005 total

includes taxes & fees

Nov 12 - Nov 13

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

12. La Pensione di Vignamaggio

Panzano in Chianti

Jacob

￥26,259 total

includes taxes & fees

Nov 13 - Nov 14

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

13. Castello La Leccia

Castellina in Chianti

Susan

￥40,073 total

includes taxes & fees

Nov 12 - Nov 13

A poolside area with lounge chairs, umbrellas, and a swimming pool.

14. Hotel Il Piccolo Castello

Monteriggioni

Frank

￥20,706 total

includes taxes & fees

Nov 15 - Nov 16

A yellow building with stone pillars, multiple windows, and a statue in the garden.

15. Villa San Lucchese

Poggibonsi

James

￥16,665 total

includes taxes & fees

Nov 29 - Nov 30

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

16. Hotel Borgo di Cortefreda Relais - Place of Charme

Tavarnelle Val di Pesa

Rahul

￥15,714 total

includes taxes & fees

Nov 27 - Nov 28

A bedroom with a stone wall, a large mirror, a bed with white linens, a potted plant, and a view through a window with curtains.

17. Terre di Baccio

Greve in Chianti

Gage

￥45,962 total

includes taxes & fees

Nov 15 - Nov 16

A stone house with a tiled roof, large glass doors, and a stone pathway leading to it.

18. The Club House

Castelnuovo Berardenga

Natalyn

￥78,807 total

includes taxes & fees

Nov 17 - Nov 18

An aerial view of a rustic village with stone buildings, a central courtyard with string lights, and a swimming pool.

19. Borgo Vescine

Radda in Chianti

Natalie

￥76,999 total

includes taxes & fees

Nov 25 - Nov 26

A spacious living area with a large window, a sofa, a green armchair, and a patterned armchair.

20. Salvadonica - Borgo del Chianti

San Casciano in Val di Pesa

Elsa

￥14,889 total

includes taxes & fees

Nov 12 - Nov 13

View all properties

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."

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 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."