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Our top choices for Chianti Region hotels

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

1. Hotel Borgo di Cortefreda Relais - Place of Charme

Tavarnelle Val di Pesa

Rahul

RM401 total

includes taxes & fees

27 Nov - 28 Nov

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

2. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Elizabeth

RM499 total

includes taxes & fees

1 Dec - 2 Dec

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

3. Castello di Fonterutoli Wine Resort

Castellina in Chianti

Micaela

RM701 total

includes taxes & fees

12 Nov - 13 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.

4. Belvedere di San Leonino

Castellina in Chianti

Kevork

RM504 total

includes taxes & fees

12 Nov - 13 Nov

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

5. Hotel Palazzo San niccolò & Spa

Radda in Chianti

Afeefa

RM351 total

includes taxes & fees

1 Dec - 2 Dec

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

6. Dievole Wine Resort

Castelnuovo Berardenga

Magdalena

RM1,245 total

includes taxes & fees

25 Nov - 26 Nov

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

7. Chapter Chianti, a Member of Design Hotels

Cavriglia

Carolina

RM1,221 total

includes taxes & fees

11 Nov - 12 Nov

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

8. Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

Ana

RM519 total

includes taxes & fees

30 Nov - 1 Dec

An outdoor patio with tables and chairs, a pergola structure, and a stone building in the background.

9. Tenuta CorteDomina

Radda in Chianti

piyanut

RM969 total

includes taxes & fees

11 Nov - 12 Nov

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

10. La Pensione di Vignamaggio

Panzano in Chianti

Jacob

RM670 total

includes taxes & fees

13 Nov - 14 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.

11. La Certosa di Pontignano - Place of Charme

Castelnuovo Berardenga

Rodolfo

RM346 total

includes taxes & fees

16 Nov - 17 Nov

A covered outdoor seating area with a wooden door, wicker chairs, and potted plants.

12. Borgo Vescine

Radda in Chianti

Natalie

RM2,088 total

includes taxes & fees

11 Nov - 12 Nov

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

13. Hotel Palazzo San Lorenzo & SPA

Colle di Val d'Elsa

Kerry

RM476 total

includes taxes & fees

15 Nov - 16 Nov

A spacious lobby with a reception desk, seating area, and a large vase.

14. Hotel Valdarno

Montevarchi

Emmanuel

RM529 total

includes taxes & fees

17 Nov - 18 Nov

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

15. Castello La Leccia

Castellina in Chianti

Susan

RM1,022 total

includes taxes & fees

11 Nov - 12 Nov

A modern bedroom with a wooden floor, a bed with a headboard, a window with curtains, and a shower area with a towel rack.

16. Park Hotel Chianti

Tavarnelle Val di Pesa

Manuel

RM284 total

includes taxes & fees

30 Nov - 1 Dec

A person sitting in a corner of a room with tiled walls and a bench.

17. Hotel Il Piccolo Castello

Monteriggioni

Frank

RM528 total

includes taxes & fees

12 Nov - 13 Nov

A cobblestone street lined with historic stone buildings, some with ivy, and large terracotta pots with flowers.

18. Hotel Borgo San Luigi

Monteriggioni

Bulent

RM532 total

includes taxes & fees

11 Nov - 12 Nov

A poolside area with outdoor seating and umbrellas, overlooking a scenic landscape.

19. Villa I Barronci Resort & Spa

San Casciano in Val di Pesa

Haris

RM375 total

includes taxes & fees

10 Dec - 11 Dec

A spacious interior with high arched ceilings, stone walls, and a central round mirror reflecting the room. Tables and chairs are arranged for dining or socializing.

20. COMO Castello Del Nero

Tavarnelle Val di Pesa

Nawaf

RM3,252 total

includes taxes & fees

16 Nov - 17 Nov

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Holiday 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...

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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.

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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

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."