A vineyard with rows of grapevines, a house surrounded by trees, and a road with vehicles.

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Check prices for these dates

Next weekend
Oct 16 - Oct 18
In two weeks
Oct 23 - Oct 25
In one month
Nov 6 - Nov 8
In two months
Dec 4 - Dec 6

Our top choices for Chianti Region guest houses

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

1. Dievole Wine Resort

Dievole Wine Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (214 reviews)
"Our recent stay at the Dievole Wine Resort was incredible! The hospitality is second to none. This is the perfect place to unwind in Tuscany. I wish we could’ve stayed longer! Ciao!"
Canada
Marissa
The price is ₩392,876
₩444,206 total
includes taxes & fees
Oct 28 - Oct 29
Dievole Wine Resort
An outdoor seating area with tables and chairs, a wooden bar, and a view of the countryside.

2. Casa di Palaia

Casa di Palaia
Greve in Chianti
9.4 out of 10, Exceptional, (31 reviews)
"This is a great place to stay if you want a relaxed feel at home experience when visiting Chianti. The owner will set you up with a good breakfast with various options like boiled eggs, bread, your selection of coffee or cappuccino and varied pastries and fruits. The view and whole scenery is awesome! We hope to be back soon!"
United States
Belisario
The price is ₩135,474
₩155,043 total
includes taxes & fees
Oct 11 - Oct 12
Casa di Palaia
A luxurious room with a chandelier, classical columns, and a dining area with wooden chairs and a table.

3. Dimora Casa Eugenia

Dimora Casa Eugenia
Loro Ciuffenna
9.2 out of 10, Wonderful, (33 reviews)
"Beautiful boutique type stay. They are so welcoming and kind. Room was spacious, bed was comfortable. Breakfast was very tasty. Walked around the village and it was beautiful. Not one complaint, book your stay! "
United States
Shannon
The price is ₩175,681
₩193,249 total
includes taxes & fees
Oct 8 - Oct 9
Dimora Casa Eugenia
A two-story building with a patio area featuring outdoor seating and potted plants.

4. Homelink Poggibonsi

Homelink Poggibonsi
Barberino Val d'Elsa
5.8 out of 10, (16 reviews)
"There was Ants in the room and property is in very bad condition "
United Kingdom
Avinash
The price is ₩55,478
₩67,053 total
includes taxes & fees
Oct 11 - Oct 12
Homelink Poggibonsi
A stone-walled room with a fireplace, a table with chairs, and a hanging light fixture.

5. Borgo Nuovo San Martino

Borgo Nuovo San Martino
Bucine
7.2 out of 10, Good, (11 reviews)
"Definitely going back in the summer"
United States
Josimar
The price is ₩136,497
₩156,174 total
includes taxes & fees
Oct 12 - Oct 13
Borgo Nuovo San Martino
A living room with a sofa, a coffee table, and a television mounted on the wall.

6. Residenze Strozzi Firenze

Residenze Strozzi Firenze
Historic Centre of Florence
8.4 out of 10, Very good, (5 reviews)
"Lovely property.. best location. Everything is 10/10 for me."
Australia
Marie Jo
The price is ₩167,492
₩202,309 total
includes taxes & fees
Oct 20 - Oct 21
Residenze Strozzi Firenze
Exterior

7. AmiRooms Affittacamere

AmiRooms Affittacamere
Siena City Centre
10.0 out of 10, Exceptional, (25 reviews)
"We received great instructions from Amina on how to access the room which were easy to follow. If arriving in the day, the ground floor is where a lovely flower shop is, then up a lift. There are then 9 easy steps down to where the room is located. This was our 4th stop on our trip and by far the best room. Although in the centre of everything, the room is super quiet, modern, with a lovely-sized bathroom & powerful shower and great WiFi. We would highly recommend and will definitely return...
United Kingdom
Michelle
The price is ₩113,047
₩130,378 total
includes taxes & fees
Nov 4 - Nov 5
AmiRooms Affittacamere
A hotel room with a large bed, a desk with a chair, a dining area with chairs, and a view of a building through open windows.

8. Palazzina Fusi

Palazzina Fusi
Historic Centre of Florence
9.2 out of 10, Wonderful, (180 reviews)
"Perfect location! Attentive staff and a very quiet room ."
United States
debbie
The price is ₩141,099
₩173,291 total
includes taxes & fees
Nov 5 - Nov 6
Palazzina Fusi
A pathway lined with trees and a large pot in the center.

9. Villa Montarioso

Villa Montarioso
Montarioso
8.8 out of 10, Excellent, (143 reviews)
"One of the best places during our stay in italy"
Canada
Michael
The price is ₩109,731
₩128,238 total
includes taxes & fees
Nov 3 - Nov 4
Villa Montarioso
A multi-story building with a classic architectural style, featuring a ground-floor entrance with a canopy and a visible storefront.

10. B&B Le Aquile

B&B Le Aquile
Siena City Centre
9.8 out of 10, Exceptional, (132 reviews)
"Everything is excellent, if I will come back I will definitely stay again, room is clean and huge for 2 and is near to the Cathedral and Plaza. Ada is an amazing person to talk to."
Canada
Lope
The price is ₩144,243
₩164,695 total
includes taxes & fees
Nov 5 - Nov 6
B&B Le Aquile
A modern bathroom with a glass shower enclosure, a vanity with a mirror, and a radiator near the window.

11. Residenza d'Epoca San Martino 29

Residenza d'Epoca San Martino 29
Siena City Centre
9.8 out of 10, Exceptional, (60 reviews)
"Such a beautiful place to stay and so handy to the main square and restraunts we loved our stay here"
United Kingdom
Cara
The price is ₩157,688
₩179,484 total
includes taxes & fees
Nov 4 - Nov 5
Residenza d'Epoca San Martino 29
A balcony with wicker furniture, a table with fruit, and a cityscape view.

12. Blossoms of Siena

Blossoms of Siena
Siena City Centre
9.4 out of 10, Exceptional, (45 reviews)
"The convenience of the hotel being so close to so many activities and a lot of restaurants within walking distance from the hotel."
United States
Walter
The price is ₩223,889
₩252,305 total
includes taxes & fees
Nov 7 - Nov 8
Blossoms of Siena
A dining area with a round table, wooden chairs, and hanging light fixtures.

13. podere la strega

podere la strega
Siena
10.0 out of 10, Exceptional, (4 reviews)
"Vår vistelse på Podere La Strega var fantastisk! Paret som hade hand om oss var alldeles underbara. Frukosten var trevlig vid ett stort gemensamt bord och god mat, mannen på hotellet ordnade en riktigt bra kaffe! Poolområdet var rent och fräsch och det märktes att de tar väl hand om stället. Vi vill åka tillbaka redan nu!"
Sweden
Jenny
The price is ₩246,569
₩277,253 total
includes taxes & fees
Oct 14 - Oct 15
podere la strega
A historic building with intricate architectural details and a dome.

14. Guest House Bel Duomo

Guest House Bel Duomo
Historic Centre of Florence
8.6 out of 10, Excellent, (1,003 reviews)
"Great location and friendly staff! Would stay again."
United States
Tracy
The price is ₩113,422
₩142,847 total
includes taxes & fees
Nov 1 - Nov 2
Guest House Bel Duomo
A balcony with a view of a pool and landscape, a wooden table with chairs, and a large umbrella.

15. Villa Sant Andrea

Villa Sant Andrea
Siena
9.2 out of 10, Wonderful, (36 reviews)
"This was our second time staying here-- so charming and AMAZING breakfast❤️❤️❤️"
United States
Sasha
The price is ₩165,155
₩187,697 total
includes taxes & fees
Nov 2 - Nov 3
Villa Sant Andrea
A storefront with a sign reading 'STUDIO GELATO' and a scooter parked outside.

16. The Florence Crown LR Collection

The Florence Crown LR Collection
Historic Centre of Florence
9.8 out of 10, Exceptional, (8 reviews)
"The room was clean and had plenty of space. Every day, the staff cleaned the room and the bathroom. I love the bid mirror. Two days before your arrival, the staff will give you all the information on how to access your room via WhatsApp, including how to access the Wi-Fi. What I loved was that there was an iron for my clothes. One more thing: the location is very close to a supermarket and restaurants, and even a hair salon. The staff is always available through WhatsApp."
United States
Vivian
The price is ₩158,215
₩192,119 total
includes taxes & fees
Nov 1 - Nov 2
The Florence Crown LR Collection
A multi-story building with a classic architectural style, featuring a central entrance with a canopy, and a series of windows on each floor.

17. Residenza d'Epoca Le Aquile

Residenza d'Epoca Le Aquile
Siena City Centre
10.0 out of 10, Exceptional, (95 reviews)
"Ada was wonderful from the first moment we spoke with her until we had to da6 goodbye when we checked. The restaurant she recommended and made reservations for us eas outstanding. She was spot on guiding us to tours around the area. She even helped us with our luggage the first day. Highly recommend!!!"
United States
Scott
The price is ₩255,199
₩286,746 total
includes taxes & fees
Nov 5 - Nov 6
Residenza d'Epoca Le Aquile
A bedroom with a bed, a TV mounted on the wall, a window with a view of buildings, and a radiator.

18. Toscanelli Residenza D'epoca

Toscanelli Residenza D'epoca
Historic Centre of Florence
9.6 out of 10, Exceptional, (394 reviews)
"This was the perfect place to stay for my trip to Florence. The location was great, right across from Boboli Gardens, down the street from Ponte Vecchio, and close by a bunch of nice restaurants and wine bars. AC works great too!"
United States
Emily
The price is ₩125,750
₩159,421 total
includes taxes & fees
Nov 6 - Nov 7
Toscanelli Residenza D'epoca
An outdoor courtyard with stone walls, arched doorways, and potted plants.

19. Residenza d'Epoca Palazzo Buonaccorsi

Residenza d'Epoca Palazzo Buonaccorsi
San Gimignano City Centre
8.6 out of 10, Excellent, (198 reviews)
"Thank you so much for a wonderful stay :)"
United Kingdom
Soni
The price is ₩113,422
₩132,298 total
includes taxes & fees
Oct 12 - Oct 13
Residenza d'Epoca Palazzo Buonaccorsi
A covered outdoor dining area with a table and chairs, a pergola with vines, and a tree in the foreground.

20. In Corte - Rooms in Florence

In Corte - Rooms in Florence
Santa Croce
8.4 out of 10, Very good, (6 reviews)
"Property was in a good location. It was very clean. Will definitely stay there again. Make sure you read check in instructions before you arrive to save you some time."
United States
Jennifer
The price is ₩128,184
₩159,089 total
includes taxes & fees
Nov 5 - Nov 6
In Corte - Rooms in Florence
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chianti Region Hotel Reviews

Castello Vicchiomaggio

Castello Vicchiomaggio

10/10 Excellent
"What a gorgeous place! We loved it here and can’t wait to go back!"
Sarah 3-night trip
Posted 2 days ago
Castello Vicchiomaggio

Find out more about Chianti Region

Chianti Region Guest Houses information

Number of reviews
1,772
Accommodation
8 Guest Houses
Lowest Price
₩67,053
Highest Price
₩444,206