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
2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct
In one month
23 Oct - 25 Oct
In two months
20 Nov - 22 Nov

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, (213 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 NZ$686
includes taxes & fees
14 Oct - 15 Oct
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, (29 reviews)
"The bedroom was large, clean and comfortable as was the bathroom. In particular the owners were very friendly and helpful."
United Kingdom
Steven
The price is NZ$197
includes taxes & fees
4 Oct - 5 Oct
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 NZ$239
includes taxes & fees
28 Sept - 29 Sept
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
6.0 out of 10, (15 reviews)
"There was Ants in the room and property is in very bad condition "
United Kingdom
Avinash
The price is NZ$88
includes taxes & fees
25 Oct - 26 Oct
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
6.8 out of 10, (10 reviews)
"Definitely going back in the summer"
United States
Josimar
The price is NZ$208
includes taxes & fees
12 Oct - 13 Oct
Borgo Nuovo San Martino
A pathway lined with trees and a large pot in the center.

6. Villa Montarioso

Villa Montarioso
Montarioso
8.8 out of 10, Excellent, (141 reviews)
"One of the best places during our stay in italy"
Canada
Michael
The price is NZ$167
includes taxes & fees
7 Oct - 8 Oct
Villa Montarioso
An outdoor courtyard with stone walls, arched doorways, and potted plants.

7. Residenza d'Epoca Palazzo Buonaccorsi

Residenza d'Epoca Palazzo Buonaccorsi
San Gimignano City Centre
8.6 out of 10, Excellent, (197 reviews)
"Thank you so much for a wonderful stay :)"
United Kingdom
Soni
The price is NZ$180
includes taxes & fees
16 Oct - 17 Oct
Residenza d'Epoca Palazzo Buonaccorsi
A narrow street lined with stone buildings, outdoor seating, and a few people walking.

8. La Casa di Ines

La Casa di Ines
San Gimignano City Centre
8.8 out of 10, Excellent, (15 reviews)
"Comfortable beds and nice and clean"
United States
Chrystal
The price is NZ$110
includes taxes & fees
19 Oct - 20 Oct
La Casa di Ines
A stone building with a large patio area, surrounded by lush greenery and a clear sky.

9. Poggio Paradiso Resort & Spa

Poggio Paradiso Resort & Spa
Torrita di Siena
10.0 out of 10, Exceptional, (42 reviews)
"Beautiful property in a very beautiful location. Breakfast is very good and the staff is extremely helpful."
United Kingdom
Giulio
The price is NZ$528
includes taxes & fees
15 Oct - 16 Oct
Poggio Paradiso Resort & Spa
A balcony with wicker furniture, a table with fruit, and a cityscape view.

10. Blossoms of Siena

Blossoms of Siena
Siena City Centre
9.4 out of 10, Exceptional, (43 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 NZ$360
includes taxes & fees
19 Oct - 20 Oct
Blossoms of Siena
A multi-story building with a classic architectural style, featuring a central entrance with a canopy, and a series of windows on each floor.

11. Residenza d'Epoca Le Aquile

Residenza d'Epoca Le Aquile
Siena City Centre
10.0 out of 10, Exceptional, (94 reviews)
"Beautiful room, convenient location. Helpful, friendly staff."
United States
Walter
The price is NZ$382
includes taxes & fees
22 Oct - 23 Oct
Residenza d'Epoca Le Aquile
A dining area with a round table, wooden chairs, and hanging light fixtures.

12. 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 NZ$315
includes taxes & fees
27 Sept - 28 Sept
podere la strega
A balcony with a view of a pool and landscape, a wooden table with chairs, and a large umbrella.

13. Villa Sant Andrea

Villa Sant Andrea
Siena
9.2 out of 10, Wonderful, (36 reviews)
"This place is a gem in Tuscany. Close to Sienna, Florence and other interesting places in Tuscany. Breakfast buffet is excellent and cappuccino and espresso coffee is awesome. Maria and Chiara are very friendly and had great recommendations what to see and best way to visit busy places. Highly recommended."
Canada
Dan
The price is NZ$274
includes taxes & fees
11 Oct - 12 Oct
Villa Sant Andrea
A modern bathroom with a glass shower enclosure, a vanity with a mirror, and a radiator near the window.

14. Residenza d'Epoca San Martino 29

Residenza d'Epoca San Martino 29
Siena City Centre
9.8 out of 10, Exceptional, (58 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 NZ$265
includes taxes & fees
22 Oct - 23 Oct
Residenza d'Epoca San Martino 29
A multi-story building with a classic architectural style, featuring a ground-floor entrance with a canopy and a visible storefront.

15. B&B Le Aquile

B&B Le Aquile
Siena City Centre
9.6 out of 10, Exceptional, (130 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 NZ$231
includes taxes & fees
4 Oct - 5 Oct
B&B Le Aquile

16. AmiRooms Affittacamere

AmiRooms Affittacamere
Siena City Centre
10.0 out of 10, Exceptional, (20 reviews)
"The room was new and very accommodating. Location was great"
United States
Mary
The price is NZ$304
includes taxes & fees
28 Sept - 29 Sept
AmiRooms Affittacamere
A courtyard with outdoor seating, a large planter, and a building in the background.

17. Relais La Corte Dei Cavalieri

Relais La Corte Dei Cavalieri
Siena City Centre
8.2 out of 10, Very good, (119 reviews)
"Easy checkin/checkout, easy with the dog also. Very nice scenery, well located, close to the train station, within the walled city. No AC but the there was a decent fan so no sweating at night despite 30C+ weather."
Canada
Ranmal
The price is NZ$148
includes taxes & fees
27 Sept - 28 Sept
Relais La Corte Dei Cavalieri
A stone building with multiple windows and a central entrance.

18. Fondaco del Moro

Fondaco del Moro
Civitella in Val di Chiana
9.6 out of 10, Exceptional, (58 reviews)
"Beautiful setting, felt like we were staying in a castle! The beds were comfortable and the property was amazing. Highly recommend this place."
Canada
Heather
The price is NZ$135
includes taxes & fees
27 Sept - 28 Sept
Fondaco del Moro
A traditional brick building with a large wooden door, a small window with a grid pattern, and a potted plant on the ground.

19. Palazzo Patrizi Suite & Spa

Palazzo Patrizi Suite & Spa
Siena City Centre
9.4 out of 10, Exceptional, (3 reviews)
"We needed an early taxi and the front desk staff ensured she called before she was even required to report for work. The maintenance workers carried our luggage down early in morning. The rooms were lovely. The location is not marked well and a bit hard to find."
United States
Rhonda
The price is NZ$570
includes taxes & fees
12 Oct - 13 Oct
Palazzo Patrizi Suite & Spa
A bedroom with a bed, bedside table, lamp, and a desk with a chair.

20. Duccio Nacci Rooms - guest house

Duccio Nacci Rooms - guest house
San Gimignano City Centre
9.8 out of 10, Exceptional, (7 reviews)
"Estadia maravilhosa, super central, limpa e atendimento super rápido dos proprietários."
Brazil
Tessa
The price is NZ$259
includes taxes & fees
27 Sept - 28 Sept
Duccio Nacci Rooms - guest house
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

Fattoria di Vegi

Fattoria di Vegi

10/10 Excellent
"This is a newly renovated and opened property cared for by a wonderful family. Everything has been taken care of down to the last detail. The food is delicious, the rooms are well appointed and till we thoroughly enjoyed exploring the property and every interesting nook! There's lots to do including a ping pong table and a beautiful pool. My only regret was not staying longer"
Patrick 2-night trip
Posted 4 hours ago
Fattoria di Vegi

Find out more about Chianti Region

Chianti Region Guest Houses information

Number of reviews
848
Accommodation
8 Guest Houses
Lowest Price
NZ$88
Highest Price
NZ$686

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