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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

￥126,975 total

includes taxes & fees

Nov 15 - Nov 16

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

2. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Elizabeth

￥19,479 total

includes taxes & fees

Dec 1 - Dec 2

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

3. La Certosa di Pontignano - Place of Charme

Castelnuovo Berardenga

Rodolfo

￥12,538 total

includes taxes & fees

Nov 9 - Nov 10

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

4. Chapter Chianti, a Member of Design Hotels

Cavriglia

Carolina

￥47,683 total

includes taxes & fees

Nov 9 - Nov 10

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

5. Dievole Wine Resort

Castelnuovo Berardenga

Magdalena

￥46,730 total

includes taxes & fees

Nov 16 - Nov 17

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

6. Hotel Palazzo San Lorenzo & SPA

Colle di Val d'Elsa

Kerry

￥18,587 total

includes taxes & fees

Nov 15 - Nov 16

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

7. Belvedere di San Leonino

Castellina in Chianti

Kevork

￥19,671 total

includes taxes & fees

Nov 12 - Nov 13

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

8. Hotel Palazzo San niccolò & Spa

Radda in Chianti

Afeefa

￥13,699 total

includes taxes & fees

Dec 1 - Dec 2

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

￥27,670 total

includes taxes & fees

Nov 9 - Nov 10

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

10. Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

Ana

￥17,442 total

includes taxes & fees

Dec 8 - Dec 9

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

￥37,850 total

includes taxes & fees

Nov 9 - Nov 10

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

12. Castello La Leccia

Castellina in Chianti

Susan

￥30,083 total

includes taxes & fees

Nov 9 - Nov 10

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

￥16,080 total

includes taxes & fees

Nov 29 - Nov 30

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

14. La Pensione di Vignamaggio

Panzano in Chianti

Jacob

￥26,160 total

includes taxes & fees

Nov 13 - Nov 14

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

15. Hotel Il Piccolo Castello

Monteriggioni

Frank

￥20,621 total

includes taxes & fees

Nov 10 - Nov 11

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

16. Villa San Lucchese

Poggibonsi

James

￥19,557 total

includes taxes & fees

Nov 9 - Nov 10

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

17. Borgo Vescine

Radda in Chianti

Natalie

￥76,712 total

includes taxes & fees

Nov 15 - Nov 16

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.

18. Terre di Baccio

Greve in Chianti

Gage

￥45,791 total

includes taxes & fees

Nov 9 - Nov 10

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

19. The Club House

Castelnuovo Berardenga

Natalyn

￥79,277 total

includes taxes & fees

Nov 15 - Nov 16

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

￥13,402 total

includes taxes & fees

Nov 9 - Nov 10

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Vacation Rentals in Chianti Region

Vacation Home

A bedroom with a large bed, a wooden ceiling, and a brick archway.

Borgo Argiano

Castelnuovo Berardenga

"Amazing staff, clean room, amazing pool!"

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...

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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.

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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

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

Top Chianti Region Hotel Reviews

Fattoria di Vegi

10/10 Excellent

"We loved our stay,"

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 Firenze Certosa camping in town

8/10 Good

"Great location, superior tent was really nice with the en-suite and balcony. Easy check in. Staff friendly and helpful. Downsides were no designated parking space for us despite not all tents being occupied. Also bread given out at dinner were not free despite us not asking for them and at €6 a bag it was not great value. The bread was pretty hard and tasteless! Regardless I would recommend a stay here in the heart of Tuscany and within half an hour bus ride into Florence ♥️🇮🇹"

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."