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

Search Guest Houses in Chianti Region from CA $69

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Check prices for these dates

Next weekend
Sep 25 - Sep 27
In two weeks
Oct 2 - Oct 4
In one month
Oct 16 - Oct 18
In two months
Nov 13 - Nov 15

Our top choices for Chianti Region guest houses

Chapel

1. Dievole Wine Resort

Dievole Wine Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (211 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 CA $498
CA $560 total
includes taxes & fees
Oct 14 - Oct 15
Dievole Wine Resort
Exterior

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 CA $124
CA $143 total
includes taxes & fees
Oct 18 - Oct 19
Casa di Palaia
27-inch flat-screen TV with digital channels, TV, heated floors

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 CA $172
CA $189 total
includes taxes & fees
Sep 22 - Sep 23
Dimora Casa Eugenia
Garden

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 CA $57
CA $69 total
includes taxes & fees
Oct 11 - Oct 12
Homelink Poggibonsi
Restaurant

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 CA $151
CA $172 total
includes taxes & fees
Sep 21 - Sep 22
Borgo Nuovo San Martino
View from property

6. Villa Gelsomino Garden

Villa Gelsomino Garden
Oltrarno
9.0 out of 10, Wonderful, (142 reviews)
"Great place nice location"
United States
Zaid
The price is CA $142
CA $179 total
includes taxes & fees
Oct 16 - Oct 17
Villa Gelsomino Garden
Garden

7. 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 CA $114
CA $134 total
includes taxes & fees
Oct 7 - Oct 8
Villa Montarioso
Standard Double Room, City View (Tornabuoni Small Size Room)

8. Toscanelli Residenza D'epoca

Toscanelli Residenza D'epoca
Historic Centre of Florence
9.6 out of 10, Exceptional, (391 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 CA $295
CA $347 total
includes taxes & fees
Oct 9 - Oct 10
Toscanelli Residenza D'epoca
Terrace/patio

9. Blossoms of Siena

Blossoms of Siena
Siena City Centre
9.4 out of 10, Exceptional, (43 reviews)
"Great location near piazza il campo. Very helpful host, lovely accommodations."
United States
Melinda
The price is CA $273
CA $307 total
includes taxes & fees
Oct 14 - Oct 15
Blossoms of Siena
3-inch Smart TV with digital channels

10. 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 CA $223
CA $252 total
includes taxes & fees
Sep 27 - Sep 28
podere la strega
Fireplace

11. Ottantotto Firenze

Ottantotto Firenze
Historic Centre of Florence
9.6 out of 10, Exceptional, (176 reviews)
"Quaint boutique hotel in great location. Clean comfortable room and nice breakfast. Wonderful restaurant almost next door and close to train station. Highly recommend."
United States
Timothy
The price is CA $361
CA $420 total
includes taxes & fees
Oct 14 - Oct 15
Ottantotto Firenze
Exterior

12. Residenza d'Epoca Le Aquile

Residenza d'Epoca Le Aquile
Siena City Centre
10.0 out of 10, Exceptional, (94 reviews)
"Fantastic location, helpful and welcoming staff, great sized rooms. 10 out of 10, would recommend."
United States
Stephanie
The price is CA $266
CA $300 total
includes taxes & fees
Sep 22 - Sep 23
Residenza d'Epoca Le Aquile
Deluxe Quadruple Room

13. Palazzo Oliveto

Palazzo Oliveto
Oltrarno
7.6 out of 10, Good, (107 reviews)
"Everything in the property was marvelous and impeccable. Plus the staff very helpful. They make our stay so enjoyable. We highly recommend this venue. It is close to all important points to visit, restaurants and shopping points. It was an outstanding experience to us. Thank you very much for your hospitality. ❤️❤️❤️"
Canada
Maria
The price is CA $128
CA $160 total
includes taxes & fees
Oct 8 - Oct 9
Palazzo Oliveto
Exterior

14. 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 CA $206
CA $233 total
includes taxes & fees
Oct 6 - Oct 7
AmiRooms Affittacamere
Courtyard

15. Drom Florence Rooms & Apartments

Drom Florence Rooms & Apartments
Historic Centre of Florence
9.8 out of 10, Exceptional, (153 reviews)
"Claudia was very helpful and kind! The hotel is a bit out of the way but a nice stay overall. Very clean and exactly what the photos look like."
Canada
Brianna
The price is CA $276
CA $323 total
includes taxes & fees
Sep 20 - Sep 21
Drom Florence Rooms & Apartments
Exterior

16. Relais La Corte Dei Cavalieri

Relais La Corte Dei Cavalieri
Siena City Centre
8.2 out of 10, Very good, (117 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 CA $96
CA $118 total
includes taxes & fees
Sep 20 - Sep 21
Relais La Corte Dei Cavalieri
Premium bedding, in-room safe, desk, laptop workspace

17. Residenza d'Epoca San Martino 29

Residenza d'Epoca San Martino 29
Siena City Centre
9.8 out of 10, Exceptional, (53 reviews)
"Enjoyed our stay."
United States
Rene
The price is CA $201
CA $227 total
includes taxes & fees
Sep 27 - Sep 28
Residenza d'Epoca San Martino 29
Front of property

18. Villa Royal B&B

Villa Royal B&B
Historic Centre of Florence
8.6 out of 10, Excellent, (115 reviews)
"Beautiful hotel and away from the busy main town, nice pool."
Italy
MINH
The price is CA $177
CA $214 total
includes taxes & fees
Oct 11 - Oct 12
Villa Royal B&B
City Double or Twin Room, 1 Queen Bed

19. Le Nove Muse Guesthouse

Le Nove Muse Guesthouse
San Lorenzo
9.6 out of 10, Exceptional, (11 reviews)
"Excellent to visit Florence"
Canada
Carolyne
The price is CA $163
CA $199 total
includes taxes & fees
Sep 21 - Sep 22
Le Nove Muse Guesthouse
Terrace/patio

20. Residenza d'Epoca Palazzo Buonaccorsi

Residenza d'Epoca Palazzo Buonaccorsi
San Gimignano City Centre
8.6 out of 10, Excellent, (195 reviews)
"Thank you so much for a wonderful stay :)"
United Kingdom
Soni
The price is CA $119
CA $139 total
includes taxes & fees
Oct 16 - Oct 17
Residenza d'Epoca Palazzo Buonaccorsi
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
"What an amazing hotel. The attention to detail on the refurb of the property is phenomenal. Once the tennis court, spa etc are completed this will easily be high hundreds per night. We visited all the other properties in the surrounding area and nothing came close to this hotel. The food and drinks were also brilliant - best meal we had in Tuscany was in the hotel. My only suggestions would be to rotate the staff more - they seemed slightly over worked. Easily one of the best hotels I have stayed in."
David 4-night trip
Posted 1 day ago
Fattoria di Vegi

Find out more about Chianti Region

Chianti Region Guest Houses information

Number of reviews
1,919
Accommodation
8 Guest Houses
Lowest Price
CA $69
Highest Price
CA $560

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