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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

￥35,209 total

includes taxes & fees

Oct 30 - Oct 31

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

2. Chapter Chianti, a Member of Design Hotels

Cavriglia

Michael

￥47,466 total

includes taxes & fees

Nov 3 - Nov 4

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

￥44,637 total

includes taxes & fees

Nov 21 - Nov 22

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

4. COMO Castello Del Nero

Tavarnelle Val di Pesa

Nawaf

￥126,399 total

includes taxes & fees

Nov 6 - Nov 7

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

5. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Elizabeth

￥18,984 total

includes taxes & fees

Nov 23 - Nov 24

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

￥16,487 total

includes taxes & fees

Nov 29 - Nov 30

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

7. Hotel Villa Campomaggio

Radda in Chianti

Dario

￥29,534 total

includes taxes & fees

Nov 3 - Nov 4

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

8. Borgo Del Cabreo

Greve in Chianti

Brian

￥29,207 total

includes taxes & fees

Oct 30 - Oct 31

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

9. Belvedere di San Leonino

Castellina in Chianti

Kevork

￥18,856 total

includes taxes & fees

Oct 30 - Oct 31

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

10. Hotel Palazzo San niccolò & Spa

Radda in Chianti

Afeefa

￥14,053 total

includes taxes & fees

Nov 16 - Nov 17

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

11. Tenuta CorteDomina

Radda in Chianti

Edgar

￥37,678 total

includes taxes & fees

Nov 3 - Nov 4

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

12. Hotel Le Fontanelle

Castelnuovo Berardenga

Cristina

￥113,325 total

includes taxes & fees

Oct 31 - Nov 1

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

13. Borgo Scopeto Wine & Country Relais

Castelnuovo Berardenga

Scott

￥65,142 total

includes taxes & fees

Nov 4 - Nov 5

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

14. Castello di Fonterutoli Wine Resort

Castellina in Chianti

Micaela

￥30,955 total

includes taxes & fees

Nov 15 - Nov 16

A courtyard with a fountain, surrounded by neatly trimmed hedges and trees, viewed through an arched doorway.

15. Pieve Aldina - Relais & Châteaux

Radda in Chianti

Paul

￥61,459 total

includes taxes & fees

Nov 1 - Nov 2

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

￥15,900 total

includes taxes & fees

Nov 29 - Nov 30

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

17. Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

Ana

￥19,011 total

includes taxes & fees

Nov 8 - Nov 9

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

18. Locanda le Piazze

Castellina in Chianti

Colleen

￥71,375 total

includes taxes & fees

Oct 30 - Oct 31

A stately building with a grand entrance, multiple arches, and a well-lit facade.

19. Fattoria di Vegi

Castellina in Chianti

Xinyi

￥40,831 total

includes taxes & fees

Oct 30 - Oct 31

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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 "

Vacation Home

A historic stone building with a central tower, surrounded by well-manicured gardens and a gravel courtyard.

Chianti Romantic Retreat

Greve in Chianti

"This is a lovely, quiet place to stay in with the benefit of a pool. We wished we gad booked for longer. It was a great self catering place and a 10 minute drive from the town of Greve in Chianti. You are in the Chianti hills and amongst vineyards. A car is essential to get to local sites, shops and restaurants."

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

Hotel Borgo di Cortefreda Relais - Place of Charme

8/10 Good

"It was a beautiful place. Location was perfect to travel around. It was very clean. Restaurant is decent and food was good. Breakfast was ok."

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."