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Aug 18 - Aug 19
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Aug 19 - Aug 20
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Aug 21 - Aug 23
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Aug 28 - Aug 30

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Our top choices for Chianti Region hotels

Breakfast included
Hotel
Pool
Bed & breakfast
Farm

1. La Certosa di Pontignano

La Certosa di Pontignano
Castelnuovo Berardenga
United States
Edyta
¥10,736
¥13,285 total
includes taxes & fees
Sep 8 - Sep 9
La Certosa di Pontignano

2. Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
United States
Alejandro
¥18,901
¥21,529 total
includes taxes & fees
Sep 13 - Sep 14
Borgo di Pietrafitta Relais

3. Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa
Radda in Chianti
Canada
Elizabeth
¥27,643
¥31,514 total
includes taxes & fees
Aug 24 - Aug 25
Palazzo Leopoldo Dimora Storica & Spa

4. Pieve Aldina - Relais & Châteaux

Pieve Aldina - Relais & Châteaux
Radda in Chianti
Italy
Matteo
¥95,911
¥106,979 total
includes taxes & fees
Aug 19 - Aug 20
Pieve Aldina - Relais & Châteaux

5. Agriturismo San Sano

Agriturismo San Sano
Gaiole in Chianti
United States
Paula
¥22,402
¥25,381 total
includes taxes & fees
Aug 30 - Aug 31
Agriturismo San Sano

6. Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais
Castelnuovo Berardenga
United States
Qingwen
¥80,992
¥90,937 total
includes taxes & fees
Aug 26 - Aug 27
Borgo Scopeto Wine & Country Relais

7. Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA
Figline e Incisa Valdarno
United States
Jason
¥24,611
¥27,810 total
includes taxes & fees
Aug 23 - Aug 24
Villa Casagrande Resort & SPA

8. Relais Vignale & Spa

Relais Vignale & Spa
Radda in Chianti
Canada
tera
¥30,845
¥39,596 total
includes taxes & fees
Aug 21 - Aug 22
Relais Vignale & Spa

9. Chapter Chianti, a Member of Design Hotels

Chapter Chianti, a Member of Design Hotels
Cavriglia
United Kingdom
Samay
¥62,757
¥70,140 total
includes taxes & fees
Aug 20 - Aug 21
Chapter Chianti, a Member of Design Hotels

10. Hotel Villa Campomaggio

Hotel Villa Campomaggio
Radda in Chianti
United States
Gregory
¥28,656
¥32,628 total
includes taxes & fees
Aug 23 - Aug 24
Hotel Villa Campomaggio

11. Hotel Il Viandante

Hotel Il Viandante
Terranuova Bracciolini
United States
Michelle
¥15,753
¥21,016 total
includes taxes & fees
Aug 29 - Aug 30
Hotel Il Viandante

12. Borgo Vescine

Borgo Vescine
Radda in Chianti
United States
David
¥112,431
¥125,151 total
includes taxes & fees
Aug 26 - Aug 27
Borgo Vescine

13. Borgo Del Cabreo

Borgo Del Cabreo
Greve in Chianti
United Kingdom
joseph
¥34,433
¥38,614 total
includes taxes & fees
Aug 21 - Aug 22
Borgo Del Cabreo

14. Dievole Wine Resort

Dievole Wine Resort
Castelnuovo Berardenga
United States
Rory
¥49,952
¥56,424 total
includes taxes & fees
Aug 26 - Aug 27
Dievole Wine Resort

15. B&B Poggiobonizio

B&B Poggiobonizio
Poggibonsi
United Kingdom
ROBERT
¥11,311
¥13,180 total
includes taxes & fees
Aug 24 - Aug 25
B&B Poggiobonizio

16. Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti
United Kingdom
Jess
¥25,569
¥29,232 total
includes taxes & fees
Aug 21 - Aug 22
Belvedere di San Leonino

17. Castello di Meleto

Castello di Meleto
Gaiole in Chianti
Canada
Vinesh
¥37,086
¥42,271 total
includes taxes & fees
Aug 20 - Aug 21
Castello di Meleto

18. Hotel Il Piccolo Castello

Hotel Il Piccolo Castello
Monteriggioni
United Kingdom
Ian
¥22,748
¥26,314 total
includes taxes & fees
Sep 1 - Sep 2
Hotel Il Piccolo Castello

19. Hotel Palazzo San niccolò & Spa

Hotel Palazzo San niccolò & Spa
Radda in Chianti
United States
gary
¥20,329
¥23,469 total
includes taxes & fees
Aug 23 - Aug 24
Hotel Palazzo San niccolò & Spa

20. Hotel Palazzo San Lorenzo & SPA

Hotel Palazzo San Lorenzo & SPA
Colle di Val d'Elsa
United States
Elizabeth Ann Brand
¥29,103
¥32,751 total
includes taxes & fees
Aug 23 - Aug 24
Hotel Palazzo San Lorenzo & SPA
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Vacation Rentals in Chianti Region

Residence

Riserva di Fizzano Residence

Riserva di Fizzano Residence
Castellina in Chianti
"Great place to stay in Tuscany! Very nice breakfast also!"
Riserva di Fizzano Residence
Townhouse

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
"Great spot"
Villa di Sotto
Apartment

Villa Il Palagio

Villa Il Palagio
Rignano sull'Arno
"Our family of five enjoyed our time at the property very much. The rooms were comfortable and the surrounding area is beautiful. The pool is a huge plus to cool down and have a relaxing time. The Rignano train station nearby makes it easy to get around Italy, by connecting to Florence’s main station. Truly an asset. The A1 highway is also nearby connecting you within easy access to beautiful Tuscany. Restaurants in the area were very good also. I would definitely stay again at Vila Il...
Villa Il Palagio
Residence

Chianti Village Morrocco

Chianti Village Morrocco
Barberino Tavarnelle
"Front desk was very helpful and very comfortable room. "
Chianti Village Morrocco
Residence

Residence Poggio del Golf

Residence Poggio del Golf
Impruneta
"Pool was a welcome treat after hard days touring, kitchenette and full fridge freezer was great, air con worked well, laundry a great bonus. Nice location Would recommend to friends"
Residence Poggio del Golf
Camping

Glamping Village Orlando in Chianti

Glamping Village Orlando in Chianti
Cavriglia
"Had an amazing stay and wished we'd had longer there"
Glamping Village Orlando in Chianti
Aparthotel

Relais Villa Belvedere

Relais Villa Belvedere
Figline e Incisa Valdarno
"True Tuscan style, beautiful views and a lovely breakfast."
Relais Villa Belvedere
Townhouse

Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
"It was perfect for my one night stop before moving on to another location in Toscana."
Antico Borgo il Cardino
Aparthotel

Podere il Pino

Podere il Pino
Poggibonsi
"Beautiful place to stay. Great for kids and has an amazing view. "
Podere il Pino
Townhouse

Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
"Very nice and quiet neighbourhood. Close to city centre. The host is very kind."
Mariani Bed & Breakfast
Townhouse

Rocca di Castagnoli

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 "
Rocca di Castagnoli
Camping

Hu Norcenni Girasole Village

Hu Norcenni Girasole Village
Figline e Incisa Valdarno
"We all loved this place. It is conveniently close to Florence or Sienna so you can take a day trips if you get bored but there are plenty of activities on site. We wished we have reserved more days to stay but we will do that next year."
Hu Norcenni Girasole Village
Apartment

Tenuta Tegolato

Tenuta Tegolato
Barberino Tavarnelle
"We stayed with our 2 years old son and it was very quiet and comfortable. Everything is very well taken care of, the place is beautiful!"
Tenuta Tegolato
Vacation Home

Chianti Romantic Retreat

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."
Chianti Romantic Retreat
Townhouse

Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
"The staff were great and the villa was amazing"
Villa Cassia di Baccano
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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 stunning cathedral and wineries in this walkable area.
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A grand, illuminated building with arched windows and a central fountain.

The Mall Luxury Outlet

8.8/10 (355 reviews)
During your visit to Leccio, you can search for that perfect souvenir at The Mall Luxury Outlet. Discover the acclaimed art scene and stunning cathedral in this walkable area.
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Tenuta Torciano Winery

9.2/10 (40 reviews)
You can enjoy a tasting or tour at Tenuta Torciano Winery during your travels to Ulignano. Discover the beautiful countryside and wineries in this quaint area.
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Castle of Brolio

9.2/10 (44 reviews)
You can find out about the history of Gaiole in Chianti with a stop at Castle of Brolio. Discover the beautiful countryside and charming coffeehouses in this walkable area.
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Verrazzano Castle

9.8/10 (10 reviews)
You can find out about the history of Greve in Chianti with a trip to Verrazzano Castle. Discover the area's countryside and wineries.
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Castello di Albola

9.0/10 (9 reviews)
You can enjoy a tasting or tour at Castello di Albola during your travels to Radda in Chianti. Discover the beautiful countryside in this quaint area, or enjoy its local tours.
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Meleto Castle

8.6/10 (10 reviews)
Find out about the history of Gaiole in Chianti when you spend time at Meleto Castle. Discover the beautiful countryside in this walkable area, or enjoy its local tours.
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Piazza Matteotti

9.4/10 (21 reviews)
Find out about the history of Greve in Chianti when you take a trip to Piazza Matteotti. Discover the beautiful countryside in this quaint area, or enjoy its local tours.
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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
A vineyard with rows of grapevines, a house surrounded by trees, and a road with vehicles.

Top Chianti Region Hotel Reviews

Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA

10/10 Excellent
"A beautiful hotel in a lovely little town. The staff were amazing, so helpful. The rooms were very clean and comfortable. I didn’t use the indoor pool or spa facilities so can’t comment on them. The outdoor pool is across the road and up a steep hill, so great if you have a car but not so much if you are on foot! Overall a very good stay."
Jonathan 2-night trip
Posted 5 hours ago
Villa Casagrande Resort & SPA
 "Villa Torre in Chianti"  Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C

"Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C

10/10 Excellent
"This was our 50th wedding anniversary celebration, and the it all went very smoothly. Thanks to Beatrice and Jacopo for their help!"
James H. 7-night trip
Posted 6 hours ago
"Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C
Belvedere di San Leonino

Belvedere di San Leonino

10/10 Excellent
"The most beautiful and breathtaking place to stay. The staff were lovely, the rooms were quiet, the views were exceptional. The breakfast was perfect. Idyllic!"
Jess 3-night trip
Posted 7 days ago
Belvedere di San Leonino
Hu Norcenni Girasole Village

Hu Norcenni Girasole Village

10/10 Excellent
"Two large pool sites. Helpful staff. Lots of entertainment. Restaurant options and a well stocked reasonably priced food market."
Katie 5-night trip
Posted 11 days ago
Hu Norcenni Girasole Village
Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent
"Just an amazing overall experience, super welcoming and hospitable staff. Vacationing in an estate that is 1100 years old makes it even more memorable. Thank you Spaltena"
Ashley 2-night trip
Posted 2 weeks ago
Castello di Spaltenna- Small Luxury Hotels of the World
Fattoria di Vegi

Fattoria di Vegi

10/10 Excellent
"Amazing hotel! Looking forward to coming back."
Harry 2-night trip
Posted 2 months ago
Fattoria di Vegi
Hotel Toscana Ambassador

Hotel Toscana Ambassador

10/10 Excellent
"Room was clean, staff was helpful and easy to park."
Jennifer 3-night trip
Posted 2 months ago
Hotel Toscana Ambassador
COMO Castello Del Nero

COMO Castello Del Nero

10/10 Excellent
"Great staff!"
Philip 1-night trip
Posted 2 months ago
COMO Castello Del Nero

More cheap stays in Chianti Region

Villa Castiglione

Villa Castiglione

Via Colle Ramole 20 Impruneta FI
¥18,893
¥21,336 total
Aug 30 - Aug 31
includes taxes & fees
8.6/10 Excellent! (276 reviews)
Villa Castiglione
Villa Norcenni Aparthotel

Villa Norcenni Aparthotel

Via Norcenni 7 Figline e Incisa Valdarno FI
¥34,561
¥38,571 total
Aug 19 - Aug 20
includes taxes & fees
Villa Norcenni Aparthotel
Castello di Pratelli

Castello di Pratelli

Via Di Pratelli 1/a Figline e Incisa Valdarno FI
Get rates
9.2/10 Wonderful! (5 reviews)
Castello di Pratelli
Agriturismo Il Caggio di Sotto

Agriturismo Il Caggio di Sotto

Loc. Il Caggio di Sotto, 26 Colle di Val d'Elsa SI
Get rates
9.6/10 Exceptional! (16 reviews)
Agriturismo Il Caggio di Sotto
Quercia Al Poggio

Quercia Al Poggio

Strada Di Quercia Al Poggio 4 Barberino Tavarnelle FI
Get ratesQuercia Al Poggio
Tenuta La Pieve Casale Presciano

Tenuta La Pieve Casale Presciano

Via di Migliari Pergine Valdarno AR
Get ratesTenuta La Pieve Casale Presciano

Hotels in Chianti Region with star-rating

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