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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

RM911 total

includes taxes & fees

30 Oct - 31 Oct

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

2. Dievole Wine Resort

Castelnuovo Berardenga

Magdalena

RM1,252 total

includes taxes & fees

28 Nov - 29 Nov

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

RM453 total

includes taxes & fees

16 Nov - 17 Nov

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

RM765 total

includes taxes & fees

3 Nov - 4 Nov

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

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

Gaiole in Chianti

Michelle

RM1,520 total

includes taxes & fees

30 Oct - 31 Oct

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

6. Borgo Del Cabreo

Greve in Chianti

Brian

RM755 total

includes taxes & fees

31 Oct - 1 Nov

A couple dining at an outdoor table with a view of the countryside.

7. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Elizabeth

RM491 total

includes taxes & fees

23 Nov - 24 Nov

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.

8. Belvedere di San Leonino

Castellina in Chianti

Kevork

RM487 total

includes taxes & fees

30 Oct - 31 Oct

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

9. Chapter Chianti, a Member of Design Hotels

Cavriglia

Michael

RM1,229 total

includes taxes & fees

1 Nov - 2 Nov

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

10. Castello di Fonterutoli Wine Resort

Castellina in Chianti

Micaela

RM832 total

includes taxes & fees

29 Nov - 30 Nov

A stone building with a circular window and a door, surrounded by purple flowers.

11. La pietra del cabreo

Greve in Chianti

Morvarid

RM837 total

includes taxes & fees

30 Oct - 31 Oct

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

12. Villa Le Barone

Greve in Chianti

Tereza

RM1,137 total

includes taxes & fees

31 Oct - 1 Nov

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

RM484 total

includes taxes & fees

29 Nov - 30 Nov

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

14. Hotel Palazzo San niccolò & Spa

Radda in Chianti

Afeefa

RM363 total

includes taxes & fees

29 Nov - 30 Nov

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

15. Tenuta CorteDomina

Radda in Chianti

Edgar

RM975 total

includes taxes & fees

10 Nov - 11 Nov

A rustic stone building with a wooden pergola, outdoor seating, and a garden with various plants.

16. Castello di Tornano Wine Resort

Gaiole in Chianti

Karina

RM716 total

includes taxes & fees

2 Nov - 3 Nov

A pool with a view of a lush valley and distant buildings.

17. Castello Vicchiomaggio

Greve in Chianti

Mary Margaret

RM835 total

includes taxes & fees

2 Nov - 3 Nov

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

18. Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

Ana

RM491 total

includes taxes & fees

8 Nov - 9 Nov

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

19. Fattoria di Vegi

Castellina in Chianti

Xinyi

RM1,119 total

includes taxes & fees

30 Oct - 31 Oct

A stone-walled dining area with a table set for four, a bench, and a view through an open doorway to the outside.

20. Borgo di Pietrafitta Relais

Castellina in Chianti

Vanessa

RM455 total

includes taxes & fees

3 Nov - 4 Nov

View all properties

Holiday Rentals in Chianti Region

Residence

A spacious indoor area with arched windows, wooden furniture, and hanging plants.

Relais Villa Olmo - Place of Charme

Impruneta

"Great property and staff. Highly recommend!"

Townhouse

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

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...

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. Visit 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

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."

Hotel Villa Cesi

10/10 Excellent

"Rooms are very clean and staff are very friendly and super helpful and above all they are caring and very accommodating especially with our elderly less abled parents for which we are very grateful. Property is in a beautiful setting. Restaurant staff also very helpful. Thank you very much to all who hosted us at Villa Cesi."

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."