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Our top choices for Chianti Region hotels

An outdoor dining area with a pool, potted plants, and umbrellas.

1. Relais Vignale & Spa

Radda in Chianti

Ron

￥35,196 total

includes taxes & fees

Oct 28 - Oct 29

A swimming pool with a stone deck, surrounded by trees and a castle-like building in the background.

2. Castello di Spaltenna- Small Luxury Hotels of the World

Gaiole in Chianti

Michelle

￥58,692 total

includes taxes & fees

Oct 30 - Oct 31

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

3. Dievole Wine Resort

Castelnuovo Berardenga

Magdalena

￥44,620 total

includes taxes & fees

Nov 21 - Nov 22

A stone pillar with carvings, a glass door leading outside, and a person sitting on a lounge chair.

4. Hotel Villa Campomaggio

Radda in Chianti

Dario

￥29,521 total

includes taxes & fees

Oct 28 - Oct 29

A wicker chair, a lantern, and a vase of flowers on a balcony with a mountain view.

5. Borgo Del Cabreo

Greve in Chianti

Brian

￥30,480 total

includes taxes & fees

Oct 28 - Oct 29

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

6. Belvedere di San Leonino

Castellina in Chianti

Kevork

￥19,573 total

includes taxes & fees

Oct 28 - Oct 29

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

7. La Certosa di Pontignano - Place of Charme

Castelnuovo Berardenga

Rodolfo

￥17,014 total

includes taxes & fees

Nov 26 - Nov 27

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

8. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Elizabeth

￥18,988 total

includes taxes & fees

Nov 23 - Nov 24

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

9. Chapter Chianti, a Member of Design Hotels

Cavriglia

Michael

￥47,446 total

includes taxes & fees

Oct 28 - Oct 29

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

10. COMO Castello Del Nero

Tavarnelle Val di Pesa

Nawaf

￥126,347 total

includes taxes & fees

Nov 8 - Nov 9

A historic estate with a central courtyard, surrounded by lush gardens and vineyards.

11. Borgo Scopeto Wine & Country Relais

Castelnuovo Berardenga

Scott

￥65,115 total

includes taxes & fees

Nov 4 - Nov 5

A large stone building with a tower, surrounded by lush greenery and a well-maintained lawn.

12. Locanda le Piazze

Castellina in Chianti

Colleen

￥71,344 total

includes taxes & fees

Oct 28 - Oct 29

A large, historic building with a tiled roof and multiple windows, surrounded by lush gardens and a stone pathway.

13. Hotel Le Fontanelle

Castelnuovo Berardenga

Cristina

￥103,076 total

includes taxes & fees

Oct 28 - Oct 29

A rustic outdoor dining area with a stone wall, wooden benches, and a table set for two.

14. Tenuta CorteDomina

Radda in Chianti

Edgar

￥37,663 total

includes taxes & fees

Nov 1 - Nov 2

An indoor courtyard with stone flooring, arched columns, and tables set up for dining.

15. Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

Ana

￥18,987 total

includes taxes & fees

Nov 8 - Nov 9

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

16. Hotel Palazzo San niccolò & Spa

Radda in Chianti

Afeefa

￥14,345 total

includes taxes & fees

Nov 26 - Nov 27

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

17. Hotel Borgo di Cortefreda Relais - Place of Charme

Tavarnelle Val di Pesa

Sergey

￥19,377 total

includes taxes & fees

Nov 27 - Nov 28

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

18. Castello di Fonterutoli Wine Resort

Castellina in Chianti

Micaela

￥28,880 total

includes taxes & fees

Oct 28 - Oct 29

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

19. Castello La Leccia

Castellina in Chianti

Samuel

￥29,636 total

includes taxes & fees

Nov 8 - Nov 9

A clear swimming pool with a view of a lush green landscape and distant hills.

20. Villa Le Barone

Greve in Chianti

Tereza

￥43,897 total

includes taxes & fees

Oct 31 - Nov 1

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Vacation Rentals in Chianti Region

Residence

A stone building with a patio area featuring a table and chairs under a large umbrella.

Relais Villa Olmo - Place of Charme

Impruneta

"Great property and staff. Highly recommend!"

Townhouse

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.

Terre di Baccio

Greve in Chianti

"Amazing property and room, only issue is it’s very understaffed so it’s hard to get anything without chasing down workers. They also don’t stay on the property so after like 11pm you’re on your own. Besides that it was a wonderful location and very peaceful."

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

"Phenomenal. We stayed 4 nights of our honeymoon at the Fattoria de Vegi and can't wait to return in the future. The staff were all so friendly and helpful, the property is set in the most beautiful quiet location with many places to lounge and explore. Everything we ate both for breakfast and from the restaurant for dinner was excellent. It was our favourite stay of the 4 locations we visited on our trip in Italy! Would recommend a cooking class also, it was a lovely addition to our stay. You can tell the attention to detail taken throughout the renovations to turn this property into an absolute class destination."

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."