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Aug 7 - Aug 8
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Aug 8 - Aug 9
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Aug 7 - Aug 9
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Aug 14 - Aug 16

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Our top choices for Chianti Region hotels

1. Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
United States
Alejandro
¥18,657
¥21,251 total
includes taxes & fees
Aug 27 - Aug 28
Borgo di Pietrafitta Relais

2. La Certosa di Pontignano

La Certosa di Pontignano
Castelnuovo Berardenga
United States
Edyta
¥14,431
¥17,332 total
includes taxes & fees
Aug 22 - Aug 23
La Certosa di Pontignano

3. Agriturismo San Sano

Agriturismo San Sano
Gaiole in Chianti
United States
Paula
¥16,945
¥19,368 total
includes taxes & fees
Aug 7 - Aug 8
Agriturismo San Sano

4. Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais
Castelnuovo Berardenga
United States
Qingwen
¥83,100
¥93,232 total
includes taxes & fees
Aug 9 - Aug 10
Borgo Scopeto Wine & Country Relais

5. Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa
Radda in Chianti
United States
Lin
¥25,019
¥28,614 total
includes taxes & fees
Aug 27 - Aug 28
Palazzo Leopoldo Dimora Storica & Spa

6. Pieve Aldina - Relais & Châteaux

Pieve Aldina - Relais & Châteaux
Radda in Chianti
Italy
Matteo
¥94,673
¥105,598 total
includes taxes & fees
Aug 10 - Aug 11
Pieve Aldina - Relais & Châteaux

7. Chapter Chianti, a Member of Design Hotels

Chapter Chianti, a Member of Design Hotels
Cavriglia
United Kingdom
Samay
¥61,946
¥69,233 total
includes taxes & fees
Aug 9 - Aug 10
Chapter Chianti, a Member of Design Hotels

8. Palagina la cascina

Palagina la cascina
Figline e Incisa Valdarno
United States
Peter
¥12,522
¥14,138 total
includes taxes & fees
Aug 10 - Aug 11
Palagina la cascina

9. Villa San Lucchese

Villa San Lucchese
Poggibonsi
United States
Simona
¥23,983
¥27,475 total
includes taxes & fees
Aug 30 - Aug 31
Villa San Lucchese

10. Castello di Meleto

Castello di Meleto
Gaiole in Chianti
Canada
Vinesh
¥23,678
¥27,504 total
includes taxes & fees
Aug 7 - Aug 8
Castello di Meleto

11. Dievole Wine Resort

Dievole Wine Resort
Castelnuovo Berardenga
United States
Rory
¥50,584
¥57,101 total
includes taxes & fees
Aug 26 - Aug 27
Dievole Wine Resort

12. Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais
Barberino Tavarnelle
United States
Sergey
¥30,722
¥34,887 total
includes taxes & fees
Aug 30 - Aug 31
Hotel Borgo di Cortefreda Relais

13. Hotel Il Piccolo Castello

Hotel Il Piccolo Castello
Monteriggioni
United Kingdom
Ian
¥22,997
¥26,572 total
includes taxes & fees
Aug 7 - Aug 8
Hotel Il Piccolo Castello

14. Tenuta CorteDomina

Tenuta CorteDomina
Radda in Chianti
United States
Dustin
¥43,306
¥48,365 total
includes taxes & fees
Aug 8 - Aug 9
Tenuta CorteDomina

15. Borgo Del Cabreo

Borgo Del Cabreo
Greve in Chianti
United Kingdom
joseph
¥47,642
¥53,135 total
includes taxes & fees
Aug 9 - Aug 10
Borgo Del Cabreo

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

Castello di Spaltenna- Small Luxury Hotels of the World
Gaiole in Chianti
United States
Rama
¥60,833
¥68,735 total
includes taxes & fees
Aug 7 - Aug 8
Castello di Spaltenna- Small Luxury Hotels of the World

17. Hotel Villa Campomaggio

Hotel Villa Campomaggio
Radda in Chianti
United States
Katelyn
¥35,031
¥39,627 total
includes taxes & fees
Sep 6 - Sep 7
Hotel Villa Campomaggio

18. Castello di Tornano Wine Resort

Castello di Tornano Wine Resort
Gaiole in Chianti
United States
Austin
¥35,217
¥40,197 total
includes taxes & fees
Aug 25 - Aug 26
Castello di Tornano Wine Resort

19. Relais Vignale & Spa

Relais Vignale & Spa
Radda in Chianti
Canada
tera
¥28,677
¥37,138 total
includes taxes & fees
Sep 5 - Sep 6
Relais Vignale & Spa

20. Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa
San Casciano in Val di Pesa
United States
Lauren
¥28,349
¥32,277 total
includes taxes & fees
Sep 6 - Sep 7
Villa I Barronci Resort & Spa
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Vacation Rentals in Chianti Region

Townhouse

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
"Beautiful property"
Villa Curina Resort
Residence

Villa San Filippo

Villa San Filippo
Barberino Tavarnelle
"This place was beautiful, quiet like a picture you’d see in the movies"
Villa San Filippo
Residence

Chianti Village Morrocco

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

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
"This is an excellent property. Very historic, rustic and with great views across the Tuscan landscapes. Lorenzo and his mother were super duper hosts who took great care of us. The property dates back to 1380 and the rooms are decorated with choicest artifacts that adds greatly to the experience. The location is fantastic too with the local market and restaurants in easy walking reach. The breakfast service is fabulous with many choices and Lorenzo himself is great chef as well! Highly recommend...
Villa il Fedino
Townhouse

Villa di Sotto

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

La Locanda di Pietracupa

La Locanda di Pietracupa
Barberino Tavarnelle
La Locanda di Pietracupa
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
Townhouse

B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
"It was a wonderful stay the bed was comfortable and the view was beautiful. "
B&B La Fonte del Machiavelli
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
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
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

Residenzia del Sogno

Residenzia del Sogno
Castellina in Chianti
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Residenzia del Sogno
Townhouse

Terre di Baccio

Terre di Baccio
Greve in Chianti
"We had a wonderful experience! The staff was kind and very helpful. Our room was stunning and very spacious for a family of 5! The breakfast was amazing, and all of the activities on site were very fun - we especially enjoyed the cooking class! I would absolutely love to return here. I recommend looking into and booking on-site activities in advance so you can get the most out of your experience!"
Terre di Baccio
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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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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 relaxing 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 romantic 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 walkable 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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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 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
"Our family of 18 stayed at the Villa this July (2026) and could not have been more pleased with everything associated with our stay. Jacopo and Beatrice truly are first class hosts. They helped us book 3 vehicles that were dropped off and picked up directly at the Villa which was a great time saver. They also provided a grocery shopping service so that we had drinks and snacks at the villa when we arrived.The meal service was truly fantastic! We opted for the Welcome dinner and the Florentine BBQ, both of which were great. We visited a lot of places while in Italy but the family dinners at sunset were among our favorites.The Villa was beautiful and spacious. The grandkids really enjoyed the open spaces and the pool. The views from the back deck of the surrounding Tuscan countryside were also very special. We even got to see hot air balloons on a few occasions. The relative close proximity to Firenze was also clutch for day trips on high-speed trains. There is a good reason why this Villa won the VRBO Vacation Rental of the Year. You simply cannot go wrong here. I am very thankful for the memories that will last a lifetime and role this villa and the hosts played in making that happen!"
Dennis K. 7-night trip
Posted 19 hours ago
"Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C
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 days ago
Castello di Spaltenna- Small Luxury Hotels of the World
Relais Vignale & Spa

Relais Vignale & Spa

10/10 Excellent
"This place is absolutely amazing. The pictures don't do it justice. The rooms are simple, but the staff, food, pool, and views are wonderful. I would highly recommend this place as a couples getaway. The included breakfast and nice parking situation were huge benefits as well."
michael 4-night trip
Posted 5 days ago
Relais Vignale & Spa
Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa

10/10 Excellent
"This was a fabulous stay. The property is beautiful, the grounds were fun to walk and the swimming pool was lovely. Breakfast every morning was delicious. Hotel was very quiet during the week but was noticeably busier starting Friday (I think local people come just for the weekend). Our room was spacious and very clean. Bed was very comfortable. There is a bar near the pool that serves drinks in the afternoon and dinner nightly on the terrace. The nearby town was so cute and had a coop as well as numerous delicious restaurants (I recommend Nonno’s for a rustic, authentic dinner, La Carboneira for pizzas and I Pini for gelato. I would stay here again and highly recommend!"
Carrie 4-night trip
Posted 5 days ago
Villa I Barronci Resort & Spa
Salvadonica - Borgo del Chianti

Salvadonica - Borgo del Chianti

10/10 Excellent
"This is the Tuscan escape you dream about! We absolutely loved our stay at Salvadonica! A peaceful retreat surrounded by vineyards, hills, and incredible sunsets! It’s perfectly situated to explore Chianti and other locations nearby. The restored farmhouse offers wonderful accommodations that are comfortable and private. There’s a refreshing pool, outdoor movies, yoga in the vineyard, and plenty of spaces to escape and relax. The onsite restaurant La Volpenera, was casually elegant and delicious! Try the gelato with the Salvadonica olive oil…you won’t be sorry. The included breakfast buffet featured a variety of options and was perfect start to each day. We signed up for the Wine and Olive Oil Tasting with Sommelier Irene which gave us a personalized tasting of Salvedonica’s products and history. Excellent experience! And we took the Cooking Class with Chef Ivana which was the best meal we had on our entire trip! Cooking with Ivana felt like we were spending the day with family! Everyone working here provided exceptional service! I only wish we had a longer stay! Can’t wait to return to Salvadonica!"
Maria 2-night trip
Posted 13 days ago
Salvadonica - Borgo del Chianti
Villa Il Palagio

Villa Il Palagio

10/10 Excellent
"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 Palagio."
Nuno 11-night trip
Posted 2 weeks ago
Villa Il Palagio
Hotel Villa Campomaggio

Hotel Villa Campomaggio

10/10 Excellent
"I was fortunate enough to stay in this beautiful hotel whilst photographing a wedding in Tuscany and I was so pleased that I am hoping to stay again as soon as I can. The staff were lovely, the hotel was beautiful and the surrounding areas were stunning. The spa was clean and calming, with three different rooms to try and a jacuzzi. I was offered a free yoga class one morning and my room was cleaned before 10am every day. On my last day, I checked out at 11am after breakfast and was offered a place to keep my bags so that I could stay out by the pooI until I needed to leave. I would highly recommend this beautiful hotel to anyone travelling through Tuscany!"
Hannah 2-night trip
Posted 1 month ago
Hotel Villa Campomaggio
Fattoria di Vegi

Fattoria di Vegi

10/10 Excellent
"Amazing hotel! Looking forward to coming back."
Harry 2-night trip
Posted 1 month 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

More cheap stays in Chianti Region

Villa Norcenni Aparthotel

Villa Norcenni Aparthotel

Via Norcenni 7 Figline e Incisa Valdarno FI
¥13,988
¥15,934 total
Aug 7 - Aug 8
includes taxes & fees
Villa Norcenni Aparthotel
Villa Castiglione

Villa Castiglione

Via Colle Ramole 20 Impruneta FI
¥19,983
¥22,528 total
Aug 20 - Aug 21
includes taxes & fees
8.6/10 Excellent! (276 reviews)
Villa Castiglione
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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